A Deep Dive on What Works in SaaS Sales, and Doesn't With Jason + Aircall's Ex-VP of Sales

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Now I finally it used to happen back in the day, but yeah, now that the brand's disappeared, it's less often.

But yeah, it's one of those things. I think I've just always read it and never heard it. So I have been saying it wrong for years. But anyhow, I want to dive into that. But before we do that, can you give the audience, I guess, a quick overview of, you know, your career leading up to that, Right? You're highly educated, you spent a lot of time in school. You know, what were your thoughts going through school? What did you plan to do and kind of. What were the series of events that led you to technology leadership?

Well, look, things have changed so much. In fact, they've changed so much. Not just since we sold Equis on Adobe sign in 2011, which is now. It's two generations ago. It's changed so much even since 2015, 2016, when we met. It's just cloud is so big and so much has changed. We can chat about, but, you know, if it's helpful to learn about one somewhat successful person's thread. For me, like, for what it's worth, everything I did was, was I, you know, was not. Not really intentional. Not accidental, but not intentional. You know, I came originally, you know, a while back, but back actually when I was briefly a startup attorney working for startups like Yahoo and others, and they were small, but I just wanted to be. I wanted to be part of tech. I wanted to work with founders. I never thought maybe the biggest learning that's so different to today, but maybe not that different from what a lot of people go through is I never thought I was good enough to be a founder. It never occurred to me I could be a founder. So I started working with startups. I loved it. It was just my blood, you know, I was a programmer when I was a kid and it's what I want to do. So I came to Silicon Valley, like many of us have done, got to work with startups, joined one of my clients. Two weeks later, we were acquired for a billion dollars. It was a crazy ride. I won't get into all the details. Ultimately, the company that acquired us went bankrupt. So I went in two weeks from having eight figures of gains to $50,000. One of those classic older, older Internet stories, it's less common, doesn't really happen in SaaS and Cloud. And then I went and joined a startup as often we did, that had raised tons of money. It looked really hot. And I got there as a total dog. It was a total dog. I got there and the third week there, I went with the CEO to visit our top two customers. Both of them canceled the contracts the third week. So we went from. And one of them was going to lead the next round. So we lost 40 million in customer contracts, went from 40 million to zero, and we lost a $50 million series seed investment. So we had no revenue and no money left. That was my third week in the job. But maybe the one of the Learnings is it looked great on the outside. So it's so hard to do your diligence. Right. And the board was fabulous and the investors were fancy.

You see that a lot there too.

What's that?

I feel like that happens a lot.

Right.

The due diligence is like no matter how deep you go. I always said I don't think that they learn quite as much as they do in the first month after the acquisition.

Yeah. The single best actually due diligence question I ever got from a vc. When I was a founder, I sat with a well known VC at the time. He since retired. We had breakfast and he said, okay Jason, I really have one final question for you. And it's like what, what's. What are the. What, what's the top thing I'm going to learn at the first board meeting? I don't know.

Now that's the question to ask on the other side.

Yeah, it's the best question. It's the best question because obviously you're.

Not volunteering the worst. Right. Like if you don't ask what founder is going to tell you.

Yeah. And then maybe just two learnings we could touch on if you want to go in the early days. So after that I joined this startup that had raised all this money and it was devastating. There's some funny stories around I won't share but ultimately I realized it was going to, going to not going to make it in its current form. But never quit. Right. So we grabbed a little bit of technology off the shelf. I grabbed a co founder, we spun out a company out of that company. We sold it for 50 million after 12 months. So I won't go into all the deals but the lesson is just never frigging quit. Right? But the meta lesson isn't really that when I think back. So we sold that company for 50 million after 12 months and we had huge challenges ahead of us. We had not built up 10 million of recurring revenue with 140% NRR. We had huge challenges and my co founder and I, she and I, we never look back, we always say look, selling for 50 million after 12 months when we had a decade of work to do and massive risk. Greatest, greatest decision on my mind. Fast forward to Adobe Sign, Echo Sign. I mean even before the acquisition closed I knew it was an error. I knew it was an error because as between signing and closing the deal, we crossed 10 million in ARR with 120. Really 140% in bigger accounts, 120% NRR. And we were cash flow Positive. So back in those days, eight years ago, nine years ago, we didn't fully understand what it meant that recurring revenue recurs. It sounds funny today, but Even when Box IPO'd Wall street made fun of SAS companies five years ago, this revenue isn't real. It's going to fail. But the number one lesson is this frigging revenue recurs for decades. And I knew I didn't get this until I had the clarity of mind. It's so hard running a company between signing and closing. When I had a mental break and I'm like, frack. If I take 10 million at 120% NRR and we don't even, and I have Brendan, but we don't even crush it in sales and marketing. We don't even do any marketing, just draw a line, we will get to 100 million. And I've seen this now with so many investments and other companies I've done, they get to. That's why our original title, remember from our first Saster event, was impossible. Inevitable. Right? 0 to 1 is impossible, 1 to 10 is unlikely. But 10 to 100, if you're committed and you have happy customers and you have positive nr, it's inevitable. Right? It's inevitable. And that's kind of the lesson that spawns saster, which is can we share this playbook so that people realize if they get their company to a certain level, they can do it, they can go big. Right. And there were no unicorns really when we started Saster and now there's 500 in SAS and cloud. So it is, you can do it. Right. And anyhow, that's, that's, that's maybe one slice of the lesson, which is if you, if you, if you have something in SAS and cloud, multiples will come and go, but if you have that 120% or north net revenue retention or maybe 105 and with SMBs and yeah. And you have a good team like settle in for decades. Settle in for decades. Because it can go forever. It can go forever.

Yeah.

Hindsight's I've seen companies like Mailchimp 20 years, Zendesk and others, they're all, all those companies are crossing a billion in ARR today. All of them. All of them at a billion. Not just some of them, all of them. And they're all going to hit 5 to 8 billion and almost all of them are going to hit 10 billion in ARR. It's crazy. The power of recurring revenue.

Yeah, it's interesting. Like I've been getting into finance and Investing lately. And I sort of had the same epiphany with compounding interest.

Right.

And I didn't realize as a young guy, like, if I put that money away and you just let it run its course, like, it just grows. And it's recurring revenue is even more.

Powerful than it does because it doesn't grow at 1% like cash does. 15 to 20%, 8% like NASDAQ historically, as until recently, it can grow like crazy. It can grow crazy in tech. Crazy in tech, Right.

So you would have held onto it now in hindsight, huh?

Oh, of course, yeah. I mean, I only think about it two or three times a day only. Yeah. But at least it is haunting, but at least it's given me the understanding of how it works. Right. I had a founder I invested in who not that long ago had an offer to buy his company for a little over a billion dollars. And the amount of money that the founders would have made, they had sold very few shares. They'd only been through one round. Really? Very interesting. Yeah. And the founder called me up and said, what should I do? It's like my investors think I should take this offer. I'm like, oh, don't sell. This is so much money. But I knew the numbers. I'm like, yeah, you're only at 40 million ARR. And so a billion is a huge multiple. Right. But you're grow, not only growing like a weed, but your customer. You have like 140% net revenue retention and you're burning nothing. Like, just go all in. Like, life is short, right? Life is short on this stuff.

Is it a hundred times harder for him to accept that reality than it is for you to give that advice?

No. At the end, he said, yeah, I just needed one person to remind me I'm not doing it.

Wow, that's impressive. I don't know if I would be that easy on that. A billion dollars is.

I know. But if the thing is in SaaS at a certain point, and this is why I knew between that signing and closing, right. At a certain point, you know, you know the risks, you know the stability, you know it. And like, you can see 12 months out so easily in SaaS after a certain point, like, you know, like, if you're ahead of sales, like, you're like, let's say you ended this year at 10 million, right? And the CEO says, I want to do 25. Okay. Right. If the customers are happy, it's not like you might end the year at 11. You and the CEO are going to be debating Whether you end the year at 18 or 20 or 22 or 24, and you might even lose your job as head of sales for not hitting that crazy number. But you're not going to grow zero, right? You have so much visibility in SaaS past a certain point if you keep investing in it, that, you know, and that you can have the confidence to say, look, yeah, if I pass up this incredible M and A offer, which makes no logical sense, right? By any historical stance, but I can say, look, in two years, I'll be back, right? And Aaron Levy has the famous story. And you know, Box has had a tough time, right? But when Aaron Levy passed on the citrix deal at 600 to 800 billion, he's like, it might be three or four years until I get back there, and it's been longer. But, you know, he's got a $3 billion company today, right? It'll be worth more. And so that's one of the crazy things is settling in for a couple decades in SaaS. I found that founders today are more comfortable doing that. They get it. We've seen the roadmap, right? Back when I started, there was only Salesforce, right? And I'm like, I can't be as good as Salesforce. I can't do that. Good. So who's my role model now? We have a hundred role models. Well, is your role model Asana? Is your role model Reich, that just got acquired for 2 billion? Is your role model Atlassian, which is worth 50? Just pick your role model or your comp and just be like, almost as good as them. You don't have to be as good as Atlassian anymore to do well. Just come up, just come close and you can have a unicorn. That's the crazy thing about today. You just come close to a leader, you can build a unicorn, which is just, you know, we couldn't even see this a few years ago, Right. I remember when we started Saster, one of the early posts was everybody lies and listed the revenue for a bunch of cloud leaders. And then HubSpot at the time I think was at 30 million an ARR or something like that, which seemed like a lot. And then they IPO'd in 2016, and when HubSpot IPO'd, they're worth $750 million. But today there was 16 billion. Wow. Yeah. So you just gotta keep. That's the thing.

I can see why. I mean, for a million reasons. But if I were a founder, you know, having this type of conversation with you would be really important. To me, every once in a while, I think, to sort of, you know, level check a little bit, because I think if you get. You get as a founder, you can get so buried in the stress and the anxiety that you get that offer for that acquisition.

You can't.

It's blinding.

Right. There's one answer to all of this, though, which is the number one advice I give. It's number one, number two, number three, number four, number five. Like, you do get buried. Right. And the bigger issue for founders is that you get tired.

Yeah. Yeah.

And you see so many CEOs sell their company after four or five or six years because that's when the grind just wears you to the ground.

And the answer, they probably just needed a vacation.

Right?

Like a nice month off, you need a vacation.

And I wrote that years ago, in the early days, like before you quit or before you quit a CEO take two weeks off and. And do no work for two weeks. But. And that still is true. That's the advice I give everybody. But the real answer, which we knew before is, is you gotta hire better VPs. You gotta hire an executive. And once you cross certain levels, like say 10 million, you have to start making yourself obsolete each year. You cannot survive as CEO. Still being the VP of sales, still being the VP of marketing, still especially see this way too often, still being the VP of product. No, you cannot. You cannot guess. Your product gets too complicated at 5, 10 million dollars. I'm sure you saw this at Air Call Aircon, the early days was. Was a simple product, right? Yep. And it still seems simple on the outside, but as the years go by, the number of features, the number of integrations, the number of workflows, it's so complicated, piles of. CEO can't be the VP of product that the company will fall apart. So you've got to, as CEO, you have to take 20 to 30% of your job each year and make. Make yourself obsolete. Get yourself out of there. And the best way is to find one great vp. That's the easy way to do it. Right. And just stop being a VP of something every year. You got to do it.

Yeah. It's really interesting hearing you say this, because I think back to my experience at Air Call and Ali, the CEO is actually really, really good at that. And it was a learning experience for me because this was a much bigger startup than I had worked at before.

Right.

They had been through some bigger growth. They're also international, so just a lot more employees and customers. But he was really good at being extremely Hands off. And it was a big shift of pace for me. And I remember my first 90 days, a big focus is like getting to know the CEO and what our working relationship and sort of cadence is going to look like.

Right.

And I remember he sat me down at one point in my second month or something. We're doing my 60 day check in, sort of. And he's like, you know that. He's like, I'm always here to help you and give you my thoughts, but you ask me for a lot of them. And I'm like, would you prefer me to just do things? And he's like, yeah, of course, you're a VP of sales. I'm like, okay. And one thing about me, and I remember getting this compliment from him in every review when you tell me something like that. And you gave me some advice before we got on this call, like, I take those things very seriously and I will spend an hour at least tonight thinking about the advice you gave me. And I did the same thing with him. And so then I implement real change. And that was something, I think that was a strength for me that he really liked about me. But anyway, you know what my point is? He was really good at that and I think that was a huge key to how they were able to grow so fast. To your point is that he really never. And part of it is natural for him. He had no desire to do those jobs. And that's why he's actually really great to be a CEO because he'd much rather focus on finding the best person to do it. Whereas I think some founders, they start out doing everything themselves, which was really not how that company was built. So he sort of had that DNA from the start to always find the talent.

Right.

He comes from a consulting background, so he was not the guy who was going to do the work. He was the facilitator. And that worked really, really well for them.

Yeah. There's a related point, I think for folks that might listen to this, there might be a lot of potential VPs and VPs to be a thing I've learned is you just said when you started there, you spent a lot of time with the CEO the first 60 days. Right. Really getting to know each other. That's the way it happens 95 times out of 100. Right. I've learned it's a mistake.

Interesting.

What I like to do today when I'm helping portfolio companies or other CEOs, recruiters, here's what I like to do. I like to get this is it's important for all VPs, sales and marketing might be the most important. I like to get them all the way to the offer letter stage. Okay. And I like the CEO to have signed the offer letter, but before it gets countersigned, I ask them to spend a half day as a working session. Okay? You've got the offer. Okay. Colin, it's yours. Okay. Now let's talk about what we're really going to do the first 90 days. Let's. And if you're. And what I especially love with ahead of sales is really look at the existing pipe. Okay. Because in the first 90 days, unless you're ultra high velocity, you're going to have to work with what you have. So what are we really going to get at what deals are in flight? Who are you going to hire? Who are you really going to hire? How are we going to get those hires done? And really do not just do the 60 to 90 day plan you do to get hired. Okay. And look smart, but actually do a work it for a half day. And sometimes at the end of that half day, 15% of the time the candidates like this is not. This is not the right fit for me. Right. And it doesn't mean they're not great because we wouldn't let it get that far. They have the sign, they have a last chance to pull the ripcord. And no one does this extra meeting between signing and starting. Right. And my rule to the CEOs is you're not allowed to change your mind.

Only the candidate back out of the offer.

It's a quiet thing. I only tell this to the candidate. I tell them the worst things happen is when two folks get married and they're great but they shouldn't be together. Right. You're a great vp. But there's going back to what we chat about earlier. There's only so much diligence you can do. Right? And it's easier. The CEO can do more diligence. The vp. The VP can talk to everyone. They can do Google, they can do this. But at the end of the day it's hard for them to do perfect diligence. Hopefully they're listening to gong on chorus calls. Please do that. Not enough people do that before they take a job. Spend hours listening to all to all of it. Um, but I want them another chance to make sure that this is a place they feel they can thrive for several years. So they need that extra session that you never quite get in the recruiting session. And it shouldn't happen after you start. Right? It's Too risky. Right? It's too risky. Because, listen, you had a CEO that loved to be hands off in sales, right? But that's not true of all CEOs. Some CEOs especially, that are good at enterprise sales. They want to be in the deals, right? And then a lot of CEOs that are good at marketing want to be very involved in marketing strategy. Right? And I find so many. So many sales folks fail because there's disalignment on what to do in the beginning, even though they're great. And so many marketers fail because they want to execute a marketing playbook that the CEO doesn't believe in.

Yep.

Okay. The marketer is like, okay, I want to do social. I want to do paid. I want to do Gartner. I want to do whatever it is. And the CEOs. No, look, I know you. I know you worked at wherever, Slack, but that's not the way it works here.

Yeah, it's different here.

Right? Okay. Let me tell you what I need is this type of dimension I need. This is working, and I just want more of it. And then I see these. The heads of marketing just flame out in new roles because they want to do their playbook, but not what the CEO wants. So they don't do this working session either. Right. And so this. In today's world, there's so many more veterans today. Right? There's SaaS, companies, they go through phase transitions and folks leave and they move on. Or the directors want VP gigs, or the right VP at 5 million is not the right one at 50 million. And there's so many great folks you can meet. But do this last step after the offer letter so the candidate does not feel like they have to oversell you. Right. Do it. And magic comes of it.

That's brilliant. I did that once with an sdr. We got a little experimental. So you're reminding me of that story. We had this guy come in for an interview. We were so tossed up. You know, it was one of those interviews, like, this guy's either going to be the best SDR we ever hire, or he's going to be the biggest pain in the neck. And usually from my history, I'm like, those are usually probably the best hires. They might also be the worst. But, like, those are the ones I'm most excited. Excited to hire because there's a lot of potential. But we were. There was. There was a lot of disagreement across the hiring teams. Anyway, we said, come in. Let's bring them in for. For a half a day or A couple hours, whatever.

Let's.

Let's get them into the training and let's just sort of start the first day and see how it goes. And we, you know, explain it to him the same way. This is a chance for you to make sure this is the right place for you, make sure you enjoy it, Get a feel of what it's like to not be interviewing here, but to be working here. And so we brought this guy out. His name is Phil Nizvetsky. He's all over LinkedIn. Uh, and the man, right, a guy comes in and this is an intimidating thing to walk into. He's coming straight out of college onto a sales floor, a bunch of people making noise, making sales. We sit him right down and I'm hands off. I paired him up with an ae. I said, teach him, you know, this process, da, da, da. Have him make some cold calls and let's just see what happens. He had done some cold calling in an internship, so he kind of knew what, how to do the calls. And he comes in and he's cranking through. And this is not an easy product to sell over a cold call, right? A phone system like this is a long process to get someone in the door. And, you know, he's bumping his head up against the wall, but I love his energy and he's learning, he's taking the coaching. So we already know we're going to hire this guy, right? And I said, hey, man, you got the job. Like, great, great stuff. You'll start on Monday. He goes, I can't leave yet. What do you mean? Because I didn't book a meeting. He goes, you came here for me to book a meeting? If you don't mind, I don't want to leave until I do that. I'm like, we'll go right ahead, right? And sure enough, within an hour, he booked a meeting. You know, he called some people he knew might be interested, but it was a legitimate prospect. And then he booked it. And so anyway, long story. Well, long story long, he turned out to be our top sdr, and now a top ae.

Yeah, it's good you did that one. The slight difference is you can take more of a risk on an SDR and AE because there's more of them. You can say, look, that high beta person is either going to be great or flame out and still do that practice day. But if she's not there in six months, it's okay. If your VP doesn't work out in six months, you could be behind setback for year for years for lose half.

Your team if they, if they liked her. Right?

Yeah. And so. But yeah, I'm with you. I'm with you.

That's great advice though because I think people are looking for tactics.

Right.

On how to hire the right vp. I know that's probably. I don't know if you break down your web traffic, but I bet there's a big, big chunk of that pie chart that's going for how to hire a VP on Saster.

Right.

Reading all that content, still true.

It's evolved over the years, but it is still true that like the number one question founders have just as they hit traction is how the hell do I find this magical VP of Sales? Right. That's part of the fun of the early days of Sasser that you'll remember. People understand this better than they did back then when it really seemed like almost a sorcerer type position. But yeah, it's still, it's still number one. It's still the number one angst and founders. Fewer founders than in the old days. But founders continue to make the mistake that they think a VP of Sales is going to solve their problems. Right. What a VP of Sales is going to do is, is let you continue your growth and tilt it. Right. But they're not.

Can you repeat that one more time?

Yes. A VP of Sales is going to do one or both things. Like they're going to let you. If you're growing very quickly, they're going to let you maintain that growth. Because founder led sales is always going to break down after two AES or threes or four AES. So if you don't hire a VP of sales, even if you're growing like rocket, your growth will always plateau somewhere between 4 and 12arr. Depending on how quickly you're growing without a VP of sales. So job one is just feed the engine, hire great. It's really ultimately hiring great people and putting systems and processes in place. If you don't do that and you're growing quickly, you'll fail. If you're growing more moderately, let's make up a number. 60%. Right. What a VP of sales can do is help you grow 80% or 90%. And that in SaaS we talked about compounding the difference between growing 60% a year and 80% or 90 or 100, it's profound. Over four or five years. Right. But what a VP of sales can't do is take a company that's not growing and magically create growth. A VP of sales can't take a company that's growing 10% a year and turn it into a unicorn. Right? That's not her job. That's not their job. Their job is to take what works with two AES or even one and a half AES sometimes and make it work with 10 and actually make it work better. Make it work better by spending every day working on this and every hour driving down sales cycles just by talking to customers more and driving deal size up by not being scared to break deals and just basic stuff, but not to create sales out of an environment with no product, market fit or leads. Right. And that's. That. That's, that's still. Most founders aren't looking for a VP of sales today too early because they don't feel like they can afford it. But, but too many people are looking for a magician, right? There is no magician.

Yes. Yes. Yeah, I always say, like, salespeople don't create demand. Right. We convert demand. And you know, I think there's, there's. And, and, and I know that's debatable because people say, well, outbound sales is creating demand. And I, I argue against that. So they're not actually creating it. What they're doing is they're contacting it. They're creating the awareness. But the demand really falls back on the marketing team. If an SDR is reaching out to them, they're creating that awareness. They might be getting that prospect to check out the company to go to the website, but then at that point the hands are really in the marketing team. The messaging on the website, the collateral, whatever, they research your reputation, they're going to do that stuff before they respond to that sdr. And that's where I see the marketing team.

If the marketing team has done a.

Good job creating that demand, then they can respond to the sdr.

It is. And it varies a little bit the more enterprise you get. But there's sort of two important learnings I've taken away from that one is, it's a shame. It's a shame. It's a shame for everyone if you hire your VP of sales before your VP of marketing.

Yes. Just had this conversation this morning with.

This was one of his posts in Sastra where I wrote, I hired my VP of Marketing at 2020 K in MRR. It wasn't a week too late. And people, people's jaws dropped back in the day. But I still see this, I see this mistake being made as much now as when I wrote that post seven years ago. And maybe it's because today cloud is bigger. So that early demand you get that early quirky organic demand you get from a blog post or a partnership. Like there's more of that in the old days. So you can get a little further without anyone in marketing than in the old days because cloud is bigger. But God, if you don't arm the sales team with, with, with, with help when they start, what's the, what's the point, right? It's, it's a waste of doing it. And so that's the number one mistake I see is miss sequencing this. Or sometimes today it's actually more common. The old days is letting a VP of sales sit for 6, 9, 12 months without a VP of marketing. A VP, not, not some little, some person with two years of experience, but without someone with a commit to sales. The most, the highest function organization is when marketing has a commit to sales. And it doesn't really matter what the commit is, whether it's opportunities. I don't like revenue, but it could be MQLs or MQOs or SQLs or S. I really don't care whether it's even raw leads. Everyone hates it, but I don't care as long as it's a frigging commit. It's a number, right?

Something start with something, a number and.

A number that progresses in the year, ideally even faster than revenue. Then magic always happens. And I see way too many companies with they finally find a VP of sales and there's no one in marketing that can own a commit for six or 12 months and you're just undermining the efficacy or the performance of your sales team. Now the flip side is the other big mistake that I am shocked still happens today. Maybe I'm not shocked is there's, you know, founders get in their mind they have to hire VP of sales, right? And they finally find someone and there's no improvement at 90 days. And I wrote this post early in Saster. The early days like you know, if VP of Sales doesn't make a difference in 30 days, they never will. They'll never work out. And people hated this post but. And all the head of sales hated it. Then they thought about it later.

They're like, you're right, I was one of those, yeah, you hated it. And then I thought more about it over time and even just thinking more about it now as you're repeating and I'm remembering back to reading that yeah, I did hate it because my perception was you really can't have much visible change in that amount of time you're working on things for the Long haul, da da da da da da. But then when you really think about it, and I went into Air Call, I'll tell you with a very different strategy around this type of lesson. And it's that you can't go in just thinking about the long term. You have to go in with sort of two different missions. And this is how I went into Air Call. I went in and I will give a lot of credit to my CEO because he actually guided me down this path, which is he wanted me to come up with quick wins, a list of quick wins. This is the first one on one I had with him. He said, in our next one on one, I want you to give me a list of quick wins that you are going to accomplish in the first 90 days. Then I also want to see an outline, high level of what you want to do in the first six months. Right. So he was getting me to think about how do you get some quick wins now? Win over some respect from the team. Just show some improvement. Do something. It doesn't have to be a major milestone, right. But just show that you're getting some stuff done. And I did that. And I don't know if I would have without him guiding me. I would have probably thought more long term and focused more on that. Because in my head you're kind of just thinking about the long term sustainability of the business. But to your point and to his point, there's a perception factor, right? You have perception of your founders, of your team, of your investors. And if you get those quick wins in actually earn their respect, everything else becomes a lot easier.

It does. And I see 100% failure rate when three months in the CEOs like, well, you know, Jason's gonna do great as a VP sales. We don't, we're not seeing in the numbers yet, but the pipeline's looking great. I've just 0% of the time have I ever seen that be a success. It's proving it to the team, it's proving it to the CEO. And it's also just the fact that no matter what situ, assuming there are leads going back to the question, you know, arm your VP of sales with a VP of marketing before they start assuming there's anything in flight, any opportunities in flight. If you hire anyone good and they spent 50 hours a week working those deals, instead of the 10 hours the CEO has, more of them are going to close. Just that. Just think about that for a minute. Let's say there's only 10 deals in flight and you join as a VP of sales. That's not great. You wish you had 100 opportunities walking in the door, but it's not zero. Let's say you walk in at 10. I bet you three of them the CEO has never even talked to. Okay, two of the 10. There's some junior AE that doesn't quite know what they're doing. Okay. And five are sort of okay. What happens if you take those two and you just call the two the CEO forgot about or got too busy? You guide the ae. That's really out of their element. Right. And you coach the other five? Let's say two of those were going to close in the first 90 days, now four will. It's just that simple. It's just by 40, 50 hours a week, helping the deals in flight. That alone is going to get you 20 to 30% more revenue out of those 10 opportunities. Right. Just. Just by increasing the odds that they close. Right. Then because you're in them, they're going to close a little bit faster because the CEO got distracted and forgot. So they're going to close. So you're going to get 20% more revenue and then they're going to close 20% faster. Right. And then a couple of them, you're going to ask, you know, I know, I know you said you needed 10 seats, but how many folks? Oh, there's 100. What if we start with 25 seats? And so you just drive up the deal size a little bit. These are all deals in flight. This is not outbound or anything. That's why there's always magic in the beginning. Even if the deal size is high, there's always magic. And the mediocre VPs to sales, the folks that are double stretches. Another classic Saster post. They don't get it. They don't get the impact they can have on the. On the opportunities that are there the day they walk in there, they don't get it. They don't get it. And they fail. They fail. Right. A great VP of Sales knows there's going to be one call closes. A great VP of Sales knows there's going to be easy deals as well as hard deals. A great VP of Sales knows that doesn't mean they're not a great VP of Sales. They have to have a different playbook for different things. And a great VP of Sales knows that if I walk in with 10 opportunities, I got to quickly figure out which are the good ones and throw some frigging energy.

Right? Right. Yeah. The quick ones go such a long way and it can Even buy you some time and take some pressure off you just to.

It's a lot of pressure off, right? And then the next thing they do in that first couple days is, especially if it's a high velocity environment, is they get rid of the one crummy AE and they bring in two good ones. And the mathematical impact of doing that, even by day 90, it's always jaw droppingly high. Right? You always find out that one terrible AE the CEO didn't realize was so bad, was just destroying deals, was saying the dumbest thing in the world or.

Remove cancer from the team too. Yeah, I mean that, that sometimes, at least for me, you know, coming in sometimes as a first time, like sometimes it's just as easy as removing someone from the team.

That's enough. Just concentrate leads in the better people. Just concentrate leads. That it's, that sounds so simple. But the folks that haven't. This is why a double stretch VP is so dangerous. Like hiring the great AE to be your vp. That's never done any of it. They don't get it. They don't get, you know what the double stretch does? They're worried about losing that person because they think they need coverage. They're worried about losing that person that doesn't perform because then they're down a man. Right? No, no, no. Someone this experience realized if I got those 20 opportunities instead of distributing them to four people, one of them is terrible. Let me just distribute them to three, the three better ones. That alone can give you a 20% revenue lift. Right? Just think about the math and trust.

Me, they'll find time to run those demos.

Yeah, it just destroys it. And so this is another reason the double stretch. I just, every time a founder proposes that like I'll give you the one, the double stretch again is someone who's never hired any successful people, never been a successful leader at any stage. I think if you can hire two great AES, you can eventually hire 200 if you're aggressive and want it. But if you've hired zero, the one exception I will say, and this is so true, is sometimes, and you've worked in the SMB world, sometimes if there's, if the velocity in SMB is so high, like it's all one call close, there's more time for a double stretch to learn the playbook. Sometimes I find in high velocity sales, just a great AE can rise to VP of sales. That's because they get a whole extra year to learn on the job. Right? But anything other than the tiniest ACVs with infinity leads, there's no time to learn. Right? There's no time to learn that on the job.

Yeah. That's exactly how I was able to move into leadership so quick is we were very transactional at my first company, Single platform, we were selling $40, $59 or $49 a month service. You know, we had to close a sale a day for every rep. And so, you know, when they moved me in to be the head of sales training at the time there was just a VP of Sales literally overseeing almost 100 person org with like just flat management. We had no training, nothing. And so I took that over for him. And to your point, like, you know, I was a first time leader in sales. I had management experience before, but it worked really well just because the process was so repeatable.

Right.

It was just about cranking it out and training. And I think for coming in as a VP Sales at a company like that, it's, it's almost just so much more focused on sales training and coaching than it is on like the executive strategic type work where you really need that experience. Because I think like my skill level as a first time VP of sales compared to when I did it the second time is significantly different.

Right.

It's not just. You wouldn't think that's just three years of experience. Like there's so many lessons learned packed into that. To get someone who's done it once versus hasn't done it, it's night and day.

Yep. And the dangerous one is the ones that think that haven't quite done it and they're just copying something. Well, you know, copying, copying.

I learned that lesson and this proves what I just said. You're backing it up.

Right.

I learned that lesson as my first time VP sales. I went to doctor.com, i spent the first six months taking the single platform playbook and rubber stamping it to a different industry and a different product. And I learned pretty quickly this doesn't work that way.

Right.

And then I had to spend the next few months really relearning a whole new industry and business and starting from scratch with a blank slate. And that was the right way to do it was instead of coming in like the know it all and trying to show everyone what I know. When I went to, that's what I did@doctor.com, when I went to Air Call. I come in and I say, show me everything. You know. Right. That was the mindset with the team is I wanted to learn from them and then try to apply Things that I've learned to the business, and it worked out significantly better. You know, it's night, night and day.

The last related point on this, and we can talk about other things you want, but the last related point to all this is, you know, do they have enough experience? Are they double stretch? Can they do it? Here's the final mistake. So many CEOs make hiring a VP sales, especially sometimes other positions. But VP sales, because they're so stressed about scaling revenue, right? They think this is magic. You have to really believe, I would say, 90% of the VPs of sales that CEOs I've worked with, where they flamed out, right? They flamed out in the first 30 to 300 days. Not all of them, but 90%. The CEO loved the spreadsheet they put together. They loved where they worked. They loved the references they loved. But, But I asked him, did you really believe that he could do it? Like, honest, deep down? No. But I don't know. I've never done this before. Like everyone. No, like, it will never work because as a CEO, you have always been the first VP sales. Even if you were terrible at it, you still did it. Someone got those first 10 customers, those 50 customers. So your gut will, like, you can't go too much on your gut as a CEO, but it's this trigger and I always see at the end and they always say, you know, I never, never really believed him, but boy, the board loved him and he was a smooth talker and that, that, you know, he said he knew everybody, but I never believed. And that's. Don't let, of course, don't fall in love with logos, right? Don't fall in love with the fact that they worked at Slack or.

I love that you preach that so, so much. Yeah, yeah. Like, especially the big co logos, you.

Know, too much, but it can fool you. But sometimes it works. But you have to love them. You have to, you have to love them. And if you do love them, the reason it also works is, first of all, if you don't love them, it's a flag that it doesn't make sense. Like, every CEO is smart enough, okay? Hopefully as CEO, you're not the smartest person in your company or you're doing it wrong, okay? That's a sign of a bad CEO if they're the smartest person in the company, but you're smart enough to know if it doesn't smell right, if it's not. No matter how good their resume is right now, if you do love them, the Beauty is every. You know, no VP of anything, especially sales, is going to be great at everything. Right? Like you know, if you're great at high velocity, inbound like when you started, you're not going to be great at big deals and enterprise and outbound or vice versa. Right? But if you believe, if you love them, if you love them, you will backfill them. You will help them and you will help them lean in where they're good and you will cut them some slack in the areas that don't and you'll give them more time and you'll even help them recruit a bit and you will backfill them. You backfill people you believe in on that report to you. Right. And you shrink and hide from the folks that you don't believe in. Right. And that backfilling, especially for almost anyone, even if you've done it all before, but especially those of it doesn't, it's having the CEO not just have your back but backfill you even quietly. That's the magic. That's the magic, Right. But you have to believe, you have to love them or you're not going to backfill them.

Yeah, I guess the judgment probably gets clouded by just that. They probably just want so badly to hand that responsibility off to someone else. Right. The sales. Right. Because especially if you're not a sales founder, which most SaaS founders are not. I don't know the percentage, but most of them are tech founders. I think like just I could imagine like the pressure of doing sales when you don't really. You're not a salesperson, you just probably want to get away from that so fast. And when you finally have the money to hire a vp, it's gotta be so tempting to just pull that trigger and dump the, the greatest responsibility, you know, onto somebody else.

It is.

Yeah. I guess the lessons learned. Right. In the long run of rushing that type of stuff. When would you say? We talked a lot about avoiding that first time VP of sales. So we're talking from the founders.

The double stretch. Not the first time. The double stretch.

The double stretch. Right, Right. Okay.

So do want to. For most of you, Most of us, Most startups should hire first time VP of sales. You should hire a great director or someone that was sort of a vp. That's a stretch because otherwise you're going to hire someone that's washed out. Who else is going to join your 11,000th 2 million ARR SaaS startup? Right. So a stretch is good. A double stretch, a stretch too far. Someone that skips steps. Too many steps. Especially doesn't work in sales. Especially doesn't work in sales.

All right, that's a good distinction. So in case anyone missed that, the double stretch is more of an AE who's never managed someone, never hired someone, moving into a VP type role. Yeah, and the stretch is sort of someone who's maybe done a little bit of hiring. Maybe they've been a sales manager and they're kind of skipping over director or something like that to be a vp, the AE one.

And just, just to push on. I don't ask the question you want to ask, but in today's world is the number one AE at a hot startup, the number one AE at Air Call in the early days, the number one AE at wherever. They're always going to get a shot at VP of sales. If I, if I look up someone on LinkedIn and Colin says this was the number one AE at air call in the early days, that person's gonna get a VP shot. Now, maybe not the VP at whatever notion or the hottest SaaS company, but they're gonna get a VP shot at a funded company because some CEO that likes to bet on scrappy is gonna say, you know who I should bet on the best day? Like sometimes you could bet on the very best engineer ever to be your cto. That actually can sort of work. We could talk about that. It can work in customer success, although it's risky, never works in sales because they have none of the hiring or management experience. That's the double stretch. And I just don't. If I had to be binary about one point. When you're tired, when you're desperate to hire that VP of sales, do not hire the best AE somewhere ever.

It's such, such, such good advice. I will say there's a but. There's might be a but to that. And maybe my career is a little bit weird, but it kind of really worked out to my advantage. I spent four years in corporate retail management and I went through an enormous amount of management and leadership training. And then I got out of that business and I went into SAS and started as an entry level salesperson. So here I am now as an ae, but I spent four years managing and leading people. Yes, I understood.

But again, you were hyper transactional. Right. That's where the inception really is. It's hyper transactional. Because that gives you a little more time to build up those jobs. Right? Hyper transactional and hyper early. Look, you can hire someone as your fifth employee that has never been a sales leader before and if they're amazing, they have time. You get an extra year if you're the fifth employee. That's where I've seen it work. Right. I saw Gayton at Algolia take them from, you know, $50 in AR to 50 million. Right. @ Algolia. And he is great and very thoughtful, but he came out of biz dev background but he was almost like a co founder. He joined so early. He had a full year. It was a year before they got to 15k in MRI when I invested. Wow. So that extra year and he made. I love him. I mean he's great, but he's made plenty of errors. But that year let him take time, find that one a really figure out the strategy. But. But as a vp, we never get a year, do we? You have to join so early. You have to join so early.

No, your year is your first 90 days.

Yeah, it's your first 60. Yeah, 60. 90 days. 60.

90 days. Right. Especially. And I knew this going into air call, I knew in my head I got brought in through a recruiting firm. So I know in 90 days if they keep me, they're paying, they're writing a check. Right. So I know that 90 day check in is really important. And so that was top of mind for me. And I actually didn't really consider that I actually had the job until that day.

That's a healthy. That is rare these days, but it's a healthy attitude.

It's the way I thought about it because I knew that they're going to spend. It's a significant amount of money. Right. It's a big percentage of your salary or whatever that they're going to have to cut and they're going to consciously have that on their calendar to make that decision before that, that 90 days. So yeah, I think that's important. I want to, I want to ask you now from the.

But it's not expensive. Let me just say one thing. I don't mean to. It's not expensive recruiting fees is that recruiters seem so expensive in the early days of a startup. They're very stressful. But if you find someone great, it doesn't matter.

Yeah, yeah.

I didn't get this as a CEO for a long time, but now when I invest, even if it's a relatively small check, like if it's too small, you can't afford recruiter. Right. I mean literally, if you have no money, I get it. But when you raise venture capital especially, you know what the number one reason that money goes in is for hiring, the second one is hiring, and the third one is hiring, and the fourth one is hiring.

So let's say you raise here, right? The vc.

Yes.

Yeah.

Yeah. So if you raise anything more than $2 million, okay. And you tell your VCs, hey, I want to, you know, we can talk about contingent versus, you know, retained search and the issues and bad recruiters. There's so many issues here. There's so many ways you can flush your money down the toilet in recruiting. Don't get me wrong, but if you spend 100 grand to get an incredible VP of Sales at your company or an incredible VP of Demand gen, I gave you $2 million. Take 5% of that and make your company better. That's. And, you know, I also, you know what I tell founders when they're like, I can't afford it? You know what I say? How about 2.1 million? Like, what will it take to make you. I'm not saying blow everybody, but like, if you think it's too expensive, I'll give you the extra 50 grand. 30 grand, 100. Like it doesn't matter. That's the difference between me investing 2 million. 2.1 is irrelevant. Right. So if, trust me, I know you're cheap and I know you would have failed if you haven't. But. But it's not. It's just something to see on the other side. Right. From your point as a candidate, you feel like it's a lot and it is a lot of money. Right. But you're, you're.

What I meant by that is it's over so much that they're going to. I just meant it's enough that they're going to think about am I keeping this person or not.

Right? Yeah, for sure. I don't think. But I don't think. I know you felt that way, but I don't think most CEOs think if they're going to keep that person, they've. Oh, my God. It's so. It's such an investment and it's so risky to bring in a VP. No. 1 I never see. I've never seen that across. Maybe interesting. My. For 25 years, I've never seen a CEO say, I'm going to decide in 90 days if this VP is going to work out. I mean, you know how much time went into finding that VP? Usually six months, 30, 100 interviews. And I find the opposite is the bigger problem is they stick with the candidate when they. When it's clear.

When it's clear, when it's Clear.

That's the danger and the compounding danger of hiring terrible AES, of not. Of not believing in the product. Right. Of. It's. It's. It's not. It's not. A good VP is okay. I wrote this post like last year showing the math of what a bad VP does. Like the deceleration in your business is tragic. Right. Keeping a good but not great VP of sales is okay, but a bad one. It's a snowball effect. Right. All of a sudden you have five terrible AES instead of one bad one. Right. And then when the sales team loses confidence, it's all over, isn't it? You never get it back. You never get it back. And I would say this is the number one issue. You have to. You have to smell a CEO. You have to smell it when your VP of sales loses confidence and it may not be their fault, it may be your fault. It may. It's often the root cause is often their last job was easier. That's almost always the root cause. Like I. Yeah, Air Call was hard because it was competitive, but that you joined something even harder and they fall apart because they had a playbook at Air Call that even with 10 competitors, it sort of worked. And then they go into this other market where instead of being like, at least having segments of the market where they're number one, they're like number four. Right. They don't know the number four playbook or they, I don't know the 10x feature, but whatever it is, when fear, when fear sneaks in, you have to. Even if you have to get rid of the entire sales team, it's worth it. It's a can. That's the biggest cancer is fear on a sales team. Right. Because those nine Nos for everyone. Yes. Once you feel it's going to be 10 out of 10, you just hide. Right.

And it's the same for an ae.

Right.

It's a mindset of a salesperson all the way from start to finish.

Yeah. That's why you have to. That's why I really think Your top couple AES should make tons of money.

Oh, you have to.

I wrote this earlier. I wrote early. Your top AE should be driving an M6 convertible. Then I made it an MA convertible. Then it was a Tesla because the cars were changing. But you need. You need two folks making tons of money on any sales team with more than six or eight folks. Two. One or two folks at least.

And do not require them to make 100 cold calls a day because they will leave.

No. And Just making and just showing that, yeah, there's something better about how she does it, but crap, holy cow. Someone can make 400,000, $500,000 a year. Someone can crush it like someone's on the person.

It's very hard to paint that picture when you come in as a VP of sales, or I will say, when you're interviewing as a VP of sales, if you find a company you feel good about, maybe you're trying to decide on a company, but you see, one of them has that rock star AE who's earning money hand over fist, the other doesn't. I would go probably with the one who does if all things are equal, because that's going to your job a thousand times easier.

Keep her and find three more like her and you'll hit the plan for the year. It's that simple, isn't it?

Yeah, it really is. Because then half the training and strategy is all figured out. Right. You just need to replicate this person's doing one.

One other, one related point, though. I wrote about this recently. I have never really talked about it. It took me a while to figure out though, which is that yes, if you're a VP of sales and you want to do something early but not too early, find one where one A is crushing it. Right? That's the cheat sheet. That's the cheat. Right. It's funny.

Things I bring up probably came from a post I read from you years ago. I wrote this one time.

I wrote this one other one I wrote recently. It took me a while to figure it out, even though I went through it with Brendan, who, you know, which is why would a great VP of Sales join a struggling SaaS company? Now, today, it was hard enough back in the day, but today, with 1,000, 2,000, 5,000 SaaS companies, every VP of Sales candidate I know, if nothing else, I can get a ton of interviews. Right. Because there's just so many SaaS companies. It's not that it's easy for either side. It's not easy, but there's so many interviews like you, you could mail your plate. Yeah. So why would you ever join one that's struggling? And so what I find is, you know, almost every SaaS company goes to. I wrote a year of hell a while ago. Or they go through. They go through a phase, transition or a deceleration and the CEOs give up, they hide and they're like, you know what? I've got to suck it up. And I cannot hire a VP of sales until I hit 100% growth again, or whatever it is. And I've learned that's a tragic error. And what I've learned is that there's just a tip. But it took me a while. Like, it helps to have an advocate. It helps to have, you know, a Jason Lemkin or a Colin saying on social media everywhere, this is a great company. Then someone will take that extra look, okay, you need a little bit of a boost. But just like the best VP of sales know, if there's one AE that's crushing it, they can create three, or at least three or four. The other thing the best AES know, the best VP of Sales know and is if there's a brand out there, if I've heard of this product and the customers are happy and there's leads and the team was terrible, that could be a gift.

That's the best start.

That's the best one. Because I'm a friggin. That's how you crush it in the first 90 days is when the leads are there and the NRR is high and the NPS is high and there's a mini brand. People have heard about it. People love this company. But the team was just terrible. It happens more often than you can think. And not every VP of sales will get it. Not the check the box person that just came out of a hot company, they won't get it. But the intellectual ones will say, let me show I know you've heard of me. That's good. And look, we had a terrible year last year, but our leads tripled and everything else, like intellectual VP of sales will take that meeting because they'll realize, man, this is a good fit for my skill set.

Yeah, the key, man, is when you're shopping for that VP job, just get an honest overview from people in the company of what are the biggest problems that need to be solved in the next six months and what are the things that are going so well that you don't even need to change them. And with those two lists, you should be able to figure out, you should be able to narrow down the list a lot.

Right?

There's obviously other factors and stuff, but there's a lot there. And I was going to ask you too. I know we're running up on time, but we got a couple of questions I wanted to ask. One, how important do you think it is to. To sort of the pairing of the VP with the actual product, the industry, what they're selling, and the personality or experience of the vp? How important is that matchup there versus everything else? We Talked about.

Yeah, I used to think about it a lot when I started investing in developer centric products and APIs. Could a B2B sales leader handle talking to a CTO? Selling to a CTO or VP of engineering?

I just went from aircall to Dasha, which is a developer platform.

Yeah. And it's certainly true that a lot of VP of sales don't want to do that. They want to work in a very certain environment and they should stick in that. Like they'll self select out. Okay. So for sure. So some folks should stick to domains that they're comfortable in. Especially sales is hard enough as it is. Selling a product you don't understand is a mistake. Yes. Yeah, we can see that.

That's why I asked actually, because the thought came up in my head before when we were talking about when you were giving the example of coming in and going through the pipeline and finding those deals where you can help really quickly. Because if the product is so new to you and the industry is so new to you, you actually can't really do that in the first 30 or 60 days. Like it's really hard at least because you run the risk of getting on the call and having no idea what you're talking about. You might be more likely to blow the sale. But very technical, right?

But what I found is two things. First of all, ACV controls everything else. At the end of the day, every 20k deal is sold the same way. Every 50k deal is sold the same way. Every 1 million dollar deal is sold the same way. So if you're very good, like that's why it's like you have to believe in them. Right. They have to have hired a couple great reps and then don't take ACV risk. You can do it. And then if the ACV is on point, like if it's a new category, it's a new space, it's confusing. But the VP of sales has sold your price point. If they in a couple hours of Google research can understand it enough, then it's okay. Then you'll get them there. You'll get them there. If a couple hours they don't get it, they don't get the value prop, then you're done. It's okay for both sides. So this is not as big an issue as it sounds. Even if they can learn enough about the space in two hours to sell you on it, the sell me the pen test does kind of work. As long as you do it the right way and it's not cheesy Right. If they can sell you that pen after a couple hours of work and the ACV is sort of similar, they will figure out all the rest. They will figure out all the rest.

When you say don't take an ACV risk, do you, what do you mean by that exactly?

Look, if you're sell like if this is the best VP sales you ever met, but she's been selling $500 a month deals, don't bring her in to sell a million dollar deals or 50k deals. I know you think it's the best person you've ever met. And the other side works too. If they've sold bigger deals, they will melt in a transactional environment. They will have, you know, big deals, know how to like get a list of named accounts, get the team together, do the outbound, but when they have a thousand leads a week to process or a day, they have no idea what they're doing and they don't take it seriously. And they hire mediocre people and they look down on the small deal sizes and it all falls apart. Right. That small business just segment falls apart. So the experience is derived at an acv, at a type of deal size, not in an industry. Got it.

Yeah, that makes people make sense.

Right? Anyone with a brain can figure out most industries at least at a sales level. And you know, I wasn't sure then I started in the early days, I started talking to a lot of folks that had gone to GitHub when GitHub was exploding. I'm like, how can you learn how to sell, you know, repo service? They're like it's 10 questions now. We do need, we do want smarter, you know, we don't want dumb people. Okay, but it's 10, it's 10 questions.

Yeah, it's like selling slack. Like hey, my storage has ran out, I need more apps, I need to sign up. Can you tell me how to do it?

Yeah, it helps to have SES and it helps to have solution architects. But, but you don't need to be technical to sell a technical product after it has a brand after it, after it's at a couple million in revenue. Right. Before that it's different.

Got it.

All right.

Do a quick sort of rapid fire wrap up. You just kind of hit on a point that, that I think is important to talk about. We, we talked a bit about when to hire the VP marketing. Do it first. Right. When to hire the VP sales, when to do this, when. Cause you just talked about sales engineers, which is, is a thing that I Don't think a lot of organizations necessarily know how to do the right way. When would you say a. That you need sales engineers? Like which. Which type of company or product? And then when do you actually start to add them into the. Into the org?

Yep. And look, we can talk about sales engineers versus solution architects and who's more technical or whatever. The simple answer is, do you already have one? And what I mean is, is the CEO have to come into deals to talk about some technical side? Does the cto, does the VP of engine. Do you drag an engine. You have to drag an eng. Even if you don't drag an engineer into the deal, do you have to go and ask a couple questions to someone on the rest of the team to close the deal? If the answer is yes, you need a sales engineer or a solution architect on the sales team. In fact, it would be great to have one today because you're wasting your fucking time and you're wasting your CTO's time answering that question when that, when that solution architect can do it just as well.

Yeah, yeah. So that's the case with my client right now, right? I have one AE and the CEO is the one to one.

It's okay. But so you know, a classic ratio in a lot of more technical companies, or even in Salesforce back in the day is sort of one for every eight, right. You'd have a, you'd have someone attached to a pod. Right. And that, that's a tax. It has a cost and has to be. It's like it has to be built into the cost of sales. But, but that 1 for 8 ratio is a rough number to think about. But if you have money, I would love to have it at a 4 because those first two AES are so different than 3 through 200. After the first two, you have to be able to hire a more diverse type of ae, not just those crazy ones that can figure out how to sell your product. And so even if the first two can be their own SE and their own VP of marketing and generate their own collateral and make their own looms like three through 300 can't. So I would love in a perfect world to have a Solution Architect by Rep3.

It's great advice. What do you look for in an SE or solution architecture candidate? Like, what's the profile for that?

I think that today it's, it's like cs. It's much easier than it was a few years back. Hire someone that's done it for a year or two somewhere and that loves your Product. Here's it, here's a case like where loving your product is even more critical. Is that first solution architect or se, they have to love your. They have to love it. They have to love it. And so the SE will be able to answer and they have to. It helps if they're like an X engineer or something like that or an exact like X. They don't have to be. Usually some of the best solution architects and ses are washed out engineers or product people that like everyone loved them, but they weren't the brilliant engineer. But they can be a brilliant advisor on how to work with a product. So that's why the simplest thing is just hire someone that held this role at another B2B company. You can hack it, I guess you could turn an engineer into it. But they're the best. And then just if they love it, if they love it and the team loves her, it's enough. It's enough. It's like the first CS hire. They don't have to have the perfect skill set. They have to have some CS experience at your deal size and just love your product and the customer. It will be infectious with the product that first csm. Right. But they have to be smart.

It's such good advice. I never thought about that, but it's so true for any new role. I'd say in a company that the level of enthusiasm, it just trickles down, right. As that team scales. And you probably never top the first one, right?

No. And the interesting insight is because of that, your first CS hire or your first solution architect, they can be from a radically different industry. You could hire someone from healthcare or even biotech or semiconductors. I've seen it work. Okay. It doesn't work for other roles. Okay. But look, if you get it, if you did a solution architect in a very different industry, but you get it, you know how an API works. You've used the product, you've already spent hours using it and you fucking love this product. You'll succeed that first couple. This because there is a generalist element for the first CS and first SC or solution architect, that that's okay, right? High IQ and a generalist with some experience and passion. That's enough. So you can have a more, a more unusual background sometimes these hires and still succeed.

It's good stuff, I guess. Last question on that topic. Who should they report to? Do they report to sales? Do they report to engineering the solution architect?

This SE type person?

Yeah, yeah.

You know, it's a nuanced question, but the truth is when you're small. The real answer is who's best at managing them. I usually find that most VPs of sales do not want to manage the sales engineer, solution architect. In the early days, most VP of sales just want to be VP of closing. Okay. They don't want it. They don't want to manage anything. They don't want to manage customer success, they don't want to manage post sales. Usually there are differences. But closers want to close. They want to close and they want. They want the assistance they need. Right. They want CS and solution. They want all the help and they want it when they snap their fingers or hit the slack. But they don't want to deal with the headaches of managing or dealing with this role. So these types of all these sort of customer support roles, prospect support roles, sales support and solution engineering. Sales engineering. The honest answer is who's the best? Is it the CEO? The cto? Sometimes it could be the VP of sales. It's a distraction, but it's more, less ideal than just who could it be?

Got it. Yeah. And that's the case, I guess, in startups a lot.

Right.

It's just people ask that question, who should SDRs report to? Who should this and that? And everyone's got opinions. But I think your answer really kind of applies everything. It's just who's the best person to do it right now? And we could change it later if we need to.

Right. That's why sometimes with SDRs, it's better for them to report to marketing in the beginning. Because sometimes if you hire a seasoned VP of Demand gen, they've managed a BDR team or SDR themselves. And if your VP of sales has just been a closer, they may not be ready to handle out. They may just want to be a client of Outbound. So even if in theory they could do a better job, just house them in marketing if they have that experience. Right.

So I always experience.

Right. Yeah. You know, I don't think it's mandatory for a VP of Demand gen to have managed SDRs, but when they have, it can give you an extra little organizational weapon in the early days.

Yeah. Take advantage of it. See who's got the strengths to manage a team and just go with it. All right, last question for you. And then if you have anything else you want to add, we'll throw it in. What, if anything, what has changed for VP sales in this new remote environment? Do you think it's epic? Yeah, I figured.

You took me a while to figure it out. It's epic. I'm excited for this because what a year of sheltering, of pretending to shelter in place but being distributed has changed and it took months for this to change. Is that a San Francisco style VP of sales that used to only want to work next to Jeff Lawson? They used to only want to work to surabo in the office. In the same office. Since that usually meant 80% of the time that meant San Francisco. Right. Because that's 80% of our. They will work for co based anywhere today. That's the difference. It took months for that to happen. Even when we were sheltering, the top VP still wanted to work. They wanted to be in the same GEO as the CEO even if they weren't, couldn't work together. Right. But that faded sometime in the fall and it took a while. It took a while to fade. Okay.

That's why I didn't take a VP sales job. I was in that phase of like we were not ready to make that commitment yet.

It's too scary. Like I get so much benefit with that back and forth with my CEO every day. And it, and it changed. And this is so disruptive for SaaS companies not based in the Bay Area especially even I'm still going to call New York and Utah secondary markets because you know, for talent it is a secondary market. Right. Atlanta. Right. It's not a tertiary market. But when 80% of SaaS companies still are born and bred in the Bay Area and the new generation, it's true, the Snowflakes and the others, they're all in the Bay Area. They're birthing new generations of leaders that you want to hire and they're still in the Bay Area actually, even though they may be working in Miami today, they're still going to come back. But they will now work for a startup based in wherever. Right. Based in Texas, based in Austin, based in France. Like this is a huge, it's not easy, but they're willing to work for international startups in ways they would never, never do before. Right. Like you're doing.

I'm doing it.

Right. Never. Yeah, never.

And so the contingency was they're taking meetings at 9pm their time. Yeah, yeah.

It's a compromise, but so if you're not based in the Bay Area and especially if you're based in Europe and you're not taking advantages, you're intimidated, you're failing your company and you're your team, you can hire Bay Area vps now based anywhere in the world. And this is more transformational than Anything else that I've seen in SaaS management in my career is that they will work that, that, you know, that's why you came to the Bay Area, right? At the end of the day, it was to hire that, those two VPs that you couldn't get anywhere else and you still can't get them anywhere else. Plenty of exceptions. Okay, but you still. But now the ones. Because they'll work for you somewhere else. It just changes everything in your management team. Right. SaaS companies I work with, we just hired a great person in Texas for a, for a Berkeley based SaaS company. Never would have gotten them before. Right. We're doing another one based in New Hampshire. We're doing. It's all over the place and it's just disruptive. It's just disruptive. We're not gonna, we are all gonna go back to field sales and we're all gonna go back to flying to meet our top customers. Because it works. Because meeting with people works. Right.

So I was gonna ask. Interesting.

Sales. This part isn't gonna change. This distributed sales we've gotten you, it's been a year and the best sales leaders I know, the best, they like it better. They like running distributed. They hated it in the beginning because they wanted to be on a floor. All the sales leaders I know have adapted and they've seen the benefit. They've realized that for recruiting and team management. And also it creates more accountability. You can't hide by just talking at the water cooler. It's actually harder in sales now because you have to hit your numbers even more. You have daily accountability instead of quarterly or monthly accountability. So sales leaders love everything about this except, you know, the interpersonal piece. And they're not going back. They are not going back to renting massive floors in San Francisco full of entitled, overpaid SDRs and AES with six months of experience there. They're not going back there. No one's going back to it. No one is going back. Even though we're going back to the office, we are not going back to the sales pit. It's not going to happen.

So we're going back to the office. Meaning the company will have an office. There'll be certain people who go to work in the office. But you think the sales team remains distributed.

I think the key for everything is when we go back, are you distributed first or not? If you're not distributed first, it all falls apart anyway. So the question is, engineering teams have already decided they're permanently distributed first. They've already changed we never thought this would happen with sales, right. It's such a person. Business sales leaders, all the top sales leaders I know have committed that when however we go back, it's distributed first. That means everyone's equal, that means zoom. First, that means no informal meetings, that means agendas, that means daily scrums, that means daily catch ups, it means standups, it means everything happens first online and second in person so that people aren't second class citizens. And so there may be multiple offices. I actually think real estate costs for startups will go up after this because we will all need more offices as part of distribution. They're not going to go down. People are foolish going to go down, it's going up. But no sales leader is going to say, hey, look, you're going to get a leg up because you're an sf because that's bad for them. So. But it's a totally different set of tools and processes and it's so much more management. Distributed teams are so the laziness that we did when we met together and you just grabbed Colin for an informal meeting when you walk down to his desk like, that's over.

That's such a good point. Like, I miss it so much. Right? And we all do. The office is so much fun. Running a sales team that will never come back. Don't miss it. It's also exhausting, right?

Yeah.

And going back to your point, if you still have offices, maybe doing that a couple times a month could be really fun.

People will rotate or people will be in an office a day or two a week. But you're not going to train by osmosis anymore. The classic way a startup trained the sales team was by osmosis. Sit in the middle of the team, you're going to get one day of training and listen. Just listen to them, right? Just listen to them on the floor. That's dead. But the investment that sales teams have made in onboarding and training and tools and systems, right, it's incredible now, right? You can actually get trained and you're.

Measuring the name of it. There's a tool, maybe you know it, it was called like stand up or something and it was so brilliant. But it was basically like Instagram stories, essentially.

Well, there's some of that. But why do you think gong is worth 2 billion now?

Oh my God.

Because Gong, Gong and Chorus before COVID were useful tools. Like we love them, like they're great, right? But. But if you're going to manage a distributed team like it's no longer an auditing tool. It's, it's required.

It's a must.

It's a must. How else you can, you can't smell the issues. You can't, you can't sniff them, you can't see them out of the corner of your eyes. I know you have to be gonging and chorusing. You have to. Right.

I just had this conversation with my client yesterday because I'm doing call reviews now. We're at that phase, you know, where we've built out the script and stuff and I'm writing notes in Google Docs. I'm like, this is a disaster. Like we just have to get. We need disaster.

Yeah, yeah. Why do you think that they.

And that's with one AE by the way. Imagine what that's like with a team of 10.

Yeah, I didn't, I did not appreciate the power of those tools in the beginning, although I knew they were necessary. Right. But co this distributed team, they didn't know. I mean gong chorus didn't know either. Right.

Well, they were turned it extremely expensive.

To mandatory to mandatory. Yeah, Very expensive. Right. A lot of complexity. The sales stack became very expensive. Right. There's a lot of sensitivity around cost sales. Yeah, but, but, but now the ones that you need for just, I mean we're just never, we're never, we're never going back. Right. But the, but now you can truly hire a sales team at least across the entire world and you know, you don't have to like, oh my God, spent all the money to open that Phoenix office and hope you can do recruiting. You may still have it, but it just changes for great sales leaders. It just.

Let me ask you this. If I'm, you know, let's say I was in San Francisco, I was a big San Francisco vp, Sales, you know, top of the market kind of kind of guy. And then I leave San Francisco, go live somewhere less expensive. Am I still getting that San Francisco OT when I get hired remotely?

Yeah, it's a good, there's, I don't, we don't yet know the answer. There's a lot of debate on it. Yeah. I think though, having worked in the past in companies that had salary adjustments for geographies and the fact that the inflation in sales in the Bay area the last four years has been astronomical, astronomical. The OTs and the expectations, there is going to be some type of deflation. And whether you see it in OTs or whether you see it in real attainment is a different question. Right. But the problem was not only did the OTs grow 30% in San Francisco in the last 24 months before COVID But the expectation, the entitled expectations grew. Right? An AE coming one year out of college to a super hot unicorn might expect they would be making 120, 140,000 a year out of college and getting.

Promoted in nine months.

Yeah. And the thing is that now that we can measure performance daily through as part of distributed teams like we'll know if the emperor has close or not. And so the best ones should make even more more quickly. But those mediocre AES that are making lots of money, they should be scared. The ones that don't really understand the product, the ones that are lazy, the ones that skated by because the hot startup had to hire 180's this year in San Francisco. Ultimately someone that wants this in Idaho or Florida or Oklahoma is going to steal their job. Their job is going to be stolen by someone that actually wants the job. It doesn't hop every six months to a higher OT without ever accomplishing anything. And that is subtly happening now. And I think because of that there will be different types of, of deflation. But we may not see it. Right? It may be slow, right? It may be slow, right? It may be reversion to the mean. But yes, I think mediocre sales folks are going to make less money after this.

Interesting prediction. I've kind of thought that the VPs might be able to still demand that bigger salary. I guess it just comes down to supply and demand is sort of what it is, right?

VP candidate salaries are so all over the place because you know the average SaaS company raises 370 million before the IPO. So if you hit it right, you know there are plenty of VP sales now that 10 years ago would have asked for a 300k at they're asking for a million, 900,000 to a million. It's pretty common today. But you can laugh. But you know what you have to deliver. That company needs to go from 10 to 50 in a year, Colin.

Yeah, yeah. Or you're out of it.

It used to be doubling was great and doubling is enough. We can do the math, right? But the best SaaS companies can go from 10 to 40 in a year. So when you take that 900k OTE, congratulations. But you know what you have to do 30 million in bookings this year and you have, you don't get a year. We get an hour in the ad about growth. Right. So what I see happening more and more is I especially see it in social groups where folks are sharing a lot of their comp is a lot of VPs that haven't earned it go in with insane expectations for OT in equity. And they either don't get the job and they don't really understand why, because they asked for the moon, or they do get in a lot of trouble. Because the other thing I've seen is when that, okay, look, the CEO doesn't feel good about it, but then they raise a $10 million round and they like, they give up. Okay, Look, Colin wants 600,000 OTE. He's a 250 guy. But like, I just raised 10 million. But remember that salary vest too, in the OT vest, right? 600,000 OTE. Let's say it's a 50, 50 split. Your first month, you're only making what, 15 grand? Like, I can take a risk and get rid of you in three weeks. And so we talked in the beginning of this conversation about you feeling under the gun for 90 days for recruiter fee. That's not the way it works. It's the massive OTE. It's pushing, pushing. Too many VPs of sales push too hard. And when you do, you'll get it in this market. But no one forgets. No one forgets.

Get shorter and shorter.

Oh, it's not just that. When you ask for the high end of normal, if your CEO loves you, like we talked about, you'll get it. Okay? If the CEO loves you, when you push beyond normal, in the old days, you wouldn't get it. Today, you'll get it. But it will never be forgotten. It will not. There will not be one day for your whole career. Now listen, if you build up the next snowflake, they'll laugh about it, but it will. You know what you'll be. You'll be laughing about it in 10 years because it'll be never. Do you want that mark on your back? I actually think most VPs of sales don't want the mark on their back. They don't want to walk in with a target on their back. And so when you look on this, on these online groups, and they all tell you to ask for the most and ask for 7% equity with a single trigger. And all these and the 10 million things, they come. And they all come with the same checklist they got on a certain online group. We won't name it. You, I will tell you this. You walk in the door with a target on your back. So leave some. At least leave something on the table and all things. And you don't. I Don't think you want that. I don't think you want a target on your back. So be careful.

Yeah. I'll give the same advice there to VPs that I give to experienced AES. Spend less time pushing for that big OTE. Spend more focus on coming in and crushing your first year and then ask for more. It's a lot easier.

Yes. The problem is, and I agree with you, the problem is that that is the right way to win. But it requires a lot of trust and a lot of confidence. And there's too many VPs of sales out there complaining about the terrible deal they got, how they got screwed over by this company. There's too much scar tissue. We all have. I have scar tissue. You have scar tissue.

Yeah.

There's too much scar tissue that people don't take that advice anymore in 2021. They just don't take it.

Yeah.

Everyone's telling them how they got how.

I give that screwed over.

What's that?

I said I give that advice. But could I take it? Like, you say that you make me think that it's true. Like, especially when you have the battle scars. Like, it's tough. It's. These are the. These are the most intense relationships you'll ever get involved in in your life as a VP to a CEO. It's, it's. It's. There's more expectations, there's more pressure than any personal relationship you ever get into to in your life.

Yes.

It's just. Yeah, there's a lot of trust issues there.

Trust issues. Yeah.

And it's just.

I guess if I had to summarize it, I would say, because I've been watching much more intense VP of sales comp negotiations last year than ever before. My advice, it's true in any. If you have to work together, this happens in M and A too. Like, you can push back twice. If I offered you. Colin, if I offered you 250kot and. And half a percent of the company. Join me. You can say, no, I want this. Okay. And then I'll give you something and then you can say again, look, thank you, Jason, but I really want this. You can do it twice. But that third time, there's also a target on your back. Like, it's too much. You're too high maintenance. Right. So just be thoughtful. About the third negotiation around VP level comp. It may be better to quietly disengage.

What do you think about. I asked you once, I ask you twice, and then I come back and I say, all right, hey, maybe there's the best of both worlds here. What about you bring me on at the 250 or whatever the offer is and we negotiate today some milestones. Right. And so if I hit X in X number of months for you, I get whatever increase. Whatever increase. And so in other words, it's sort of what I suggested before.

Any good CEO will take that deal.

Any good CEO will take that deal.

Any good CEO will take that deal. Yeah, those. Any good CEO will take a deal where you bet on yourself and it aligns your interest. In fact, you can get a better deal if you're willing to trust her, trust them and do it. If you have a step function where the first one is close to, where they're not just what they asked for, but their comfort level, the CEOs comfort level. And then you have a step up, that's your comfort level and you agree on why the step up happens. It's not time based, it's performance based. Any great CEO that has money in the bank is going to give that. They're going to give that to you. You, they're going to give it to you. In fact, they're going to agree to it almost instantly.

It's the best way, I think, to come in and position yourself for a lot of money, whether it's as an experienced AE or a VP or director, whatever. Come in and get a decent fair market value. But negotiate some milestones and then go crush it.

It is.

And then you get what you wanted. Because the alternate to that is you push and push and push and get the money up front. But then you may not keep your job anyway because you may not deliver. And then in hindsight, you would have rather have the smaller salary and still have some more time.

Right.

That's why I think those milestones are really the answer to that problem.

Yeah, I mean, listen, you can feel like you get screwed. There's risk in these scenarios, but there's risk anyway, right?

Always.

What people don't get. If you're willing to do that step function right, prove yourself and then get that bigger comp. The truth is, here's why it's clever from a negotiation perspective is you start, you stay in the comfort zone, which makes it very. Which, which is the nice place to start. The truth is, anything that's contingent like that gets fully budgeted. Okay. If you and I agree on a 225 OT, but you get 450 when you hit your plan quietly. I budgeted for 450. Okay. Now there could be friction about when that Date happens. People don't like that. We may disagree. If the. What if the milestones 80% hit. Like there's a lot of dramas around that, right.

I think it should be. Be very clearly negotiated, right? Like. Like, yeah, yeah.

But the trick that people don't get is they think it's not budgeted. So you're already saying, look, if this works out, you're a 450 guy, okay? If it works out. And so you've been quietly budgeted. And so if you're going long and you're. It works to your advantage because even if there's some friction that your target OT has been budgeted and so you don't have to figure it out later. Right. You don't have to convince a company that only budgeted less it's been budgeted. Right. And we all know that a new and sell that being budgeted is magical. Right.

It makes all the difference because the alternative is that you're spending that first year just paranoid and thinking about that future negotiation. You get it out of the way up front. It's like a prenupt in a way.

Right.

Like you're just getting the dirty talk out of the way so that you know, you can just focus on executing and your CEO doesn't have to worry because they're protected.

Right.

Because these are milestone increases. Yeah. Jason, before we, before we depart here, what's going on at Saster, man, I mean this must have been an insane year for you, right? A huge events based business, you know, moving to remote. You had one planned. I remember you're like just. I probably sit in fingers crossed like trying to. Trying to make it happen.

It was horrible.

Did you guys pivot?

Yeah. We were the first big tech event. We were the first big tech event that got hit by Covid, right. That had to cancel. We lost $10 million. $10 million. Wow. 10 million.

You would have never thought to have insurance on that, right?

You know, it's funny. Yeah. There is insurance. We. It turns out it's hard to get and a lot of folks are suing their insurance agencies that do have it. Right. So. But yes, it was so unforeseen. I think the, you know, a lot of, A lot of fun lessons out of it. Sure. It was, it was tough. What first, what I realized looking back of my career is about every four to five years there's a black swan event. And so now I've been doing this long enough, I plan for one like you people will talk about 2008 to that like no one foresaw the depth of the crash in 09. No one even foresaw the flash SAS crash of 2015. No one foresaw Covid. But when you add these all up, you see they happen about every four to five years. In fact, I sent my, you know, really, my co founder Sastra Amelia, who runs most of things, I sent her this email in January and I said, Covid is going to be our Black Swan event in January. As soon as the CDC first said it might be a big deal, I said, I can show you this email. I said, this is. This happens every four to five years. This is ours. And no one quite got it. But I already knew because I knew the playbook, right? So we already. There was only so much we could do. We had, you know, $15 million committed. But we are. I had already. I put the things in motion to see. I didn't think we would get shut down. I do. I did think it would be, you know, that's why if you looked early, like we were written up at the Wall Street Journal, people made fun of us for saying we had to have social distancing and washing our hands and wearing masks because no one was doing this. But I knew in January, like I have to do everything to make this happen. This black.

And you hung on for a while too, right?

I think because we did everything. We did. No one else did anything. We did everything.

Yeah, everyone else was canceled. You guys really, really pushed to try to make it happen.

The last minute, the warriors still played for another week, but we went down. But so the black as a co plan for a Black Swan event every four to five years. And when you smell one coming, do something about it, right? Do something about it. And then that's the real lesson for everybody. I mean, if you're curious, for us, you know, then we went through what a lot of folks went through is we have a tiny team, but we're at scale, right? It's weird. We have a small amount of people doing something massive and about half our team left afterwards. They just decided the new world was not the place for them, right? And you'll see that happen in companies, right? And it kind of sucked, but we got stronger out of that, right? And you know, we'll probably, you know, and then I can briefly touch on the investing side and we'll run out of time, but we'll probably do 20 million this year at the end. So we came out of it, but, you know, it was terrible. We lost 10 million. We had four months with no revenue I had a large payroll. Everyone makes a lot of money. It's aster we pay people. Really?

What did you guys do last year?

I think we did 12 or 13.

Oh, so you're growing. That's, that's not.

This year will be a mess, but next year will be 20. Yeah, it'll be 20. So. And we tilted. You know, we tilted and like we'd never done a digital event or anything, but we'll do 4 to 5 million over 12 months in digital events and digital media versus zero the year before. So you know the team, you know the meta lesson there is, look, if you have a few great people, you gotta be as a leader. Like, the team was devastated. For 90 days we had no revenue. People were running around with their heads cut off. People were despondent. But as your CEO, your job is to find things. I'm like, you know what, let's. There's some like cloud is coming back. There's so much money field. Marketers want leads. Let's try something. And out of that, we did it our own way. That was very founder centric and not in commercial, but we built a four to five million dollars business in one year out of it. And so your best people can't always do it on their own. SEO, you have to find the vision for them, right? You have to prove it out. But then once you have some proof points, just let them fucking go, right? And they built it and they did something that I think no one else in the industry has done. And then lastly, on investing side, investing was grim for about eight weeks, but oh my God, I mean, now investing like, I mean, as an investor, you ended up being lucky. In the last half of the year, I did nothing right? And all my investments doubled. Doubled as a group in the last six months, a year doing no work.

Wow.

Cloud guys. I mean cloud, you can just see it in the slacks. And I'd invest in Slack and Zoo, but even the great ones I've invested in, you know, you can, you can. They just so many of them tripled. They just triple.

Were you in Zoom pre Covid?

No, I didn't invest. But I'm just saying. That's an obvious one. But I'm saying it happened all across Cloud. Like you were at Aircraft. Like look at Talk Desk. It went from 1 to 3 billion almost overnight during COVID It'll end up being a $10 billion company because of COVID Right? Gorgeous and others we talked about, they almost quadrupled their valuation during COVID It happened all across the Board in segments that were benefit air call. Yeah. So investing was weird, which is that if you just invested early enough in SaaS you became a genius at the end, at the back half of 2020. And it's just crazy. Whether it's sustainable and whether it really makes sense is a different question. But for the SASTER Inc. I mean, yeah, I mean, you know, events and parts of tourism and travel and offices just. These are devastated industries. But it's fun to come back from it. It's fun, you know, it's fun to triumph over adversity. I mean it sucks. But anyhow, blacks wanted that. It's gonna happen. They happen like clockwork.

Is the. It's funny that you just knew that was coming too, like right as you saw it is the plan today to get back to live events. Do you think that that's.

We will. If, if vaccines go as we expect and the county does it, then we will have a SAS or annual live in September. We'll have mainly outdoors. It'll be outdoors. It'll be at the San Mateo county fairgrounds so that no matter, even if we're vaccinated, we're, It'll be like a festival. We'll all be outside for 99% of it. I think if we, you know, there's, it's, there's a lot to get through between now, but it certainly appears there's a lot of pent up demand.

Well, you know what, that's why I asked you because I thought that you would have, you know, that you'd have a strong answer one way or the other. And I feared that you would say we're just gonna, that it's just gonna stay online because I, I hope that those things come back. Right. And it's gonna take people like you to really push to take the risk to do it.

We're gonna push it.

Yeah.

Otherwise we're not gonna take any help or safety risk. Right. We were the opposite. You saw us. We were the most safe there was going into this. We'll be the most safe, but we will push it. We will take the financial risk and other. We've already put a lot of money into September and it may not happen like we, it may be safe, but the county or California, Northern California. I mean right now I'm in Orange County. No one cares here. No one wears a mask and there's no social distancing. But Northern California is the most conservative in the country. Right. So everything may be fine. But Northern California may say we're going to take A pass for the whole year. Right. And so we'll lose a million bucks again, but we're investing in it as if it's going to happen.

I love that. I'm glad to hear that. And it is interesting how, like, the culture around Covid right now is so different in different places. I was in New York. Everyone masks social distance. I come to New Jersey. No one cares. Right here. Yeah, yeah.

I'm right now, for family reasons, I'm in Orange county, and people just line up at the hot spots with an inch between them and no mass at all. The hot spots in Newport Beach.

Oh, and once there are a few drinks in at the bar, the masks are off. Forget about.

And nothing. All the people are eating indoors at restaurants, even though it's illegal. I mean, there's no one. No one cares, right? No one cares.

Well, I think so many people have caught it by now, like, myself included. It's weird to even say that because I never got really sick, but, like, I've caught it now. It's like, I'm complicated.

I'm only interested in the business side and how it impacts tech because there's too many complicated issues there. But you could imagine where the rest of the country is pretty cool with things in the fall. But the Bay Area is the one exception. Right. So what would we have sas, Trania? Will we do something crazy like do it in Florida or Vegas? It's too early. But right now we've got the San Mateo county fairgrounds booked. It'll be outside. Everyone will come. And if we can do it, I think it'll be one of the most fun things we've done since the beginning. Right. Because people will be excited.

Because it's like just doing it, starting all over again. I love that. All right, real quick, before you go, any hot tools that are out there that are making remote onboarding or remote events better that you are aware of? Just so we have a couple tips in there, because I think for remote onboarding, I don't even think the technology is started yet. Like, I think there's going to be so much that needs to be done to onboard sales teams, like, remotely. I just think we're.

I'm the wrong one to ask. I will just give you two insights and then we can break. One is that I think Notion is the distributed worker dashboard. So I think Notion is as hot as it is. I think it's undersold everything that sasters run on Notion today. And we use all the other tools, but Notions are bedrock, and we're not, we're not going back. Right. So if folks on your team talk about Notion but you don't get it, you don't see why it's useful. It looks like the 10,000th markup tool. Empower your team because this is a powerful tool that is in some ways the OS of distributed teams. As I think Notion is on events. It's just interesting because there's been so much investing. They're all terrible. They're all terrible.

Which one did I use?

Well, Hopin is the most successful, right?

That's what I used and it had bugs. But I thought it was very impressive just because I had no idea something like that even existed.

Hopin is slick and it's very interesting. The industry's move so quickly, right? Hopping went from nothing to 2 billion evaluation in 10.

Talk about time.

All the products now have cloned them and there's now there's basically a Hopping ui. Like everything looks like Hoppin now.

Oh really? It's like sales loss all over again.

And I like and I like but these products, and I think Hopping in particular will be successful because the CEO is so committed and they have so much capital. But what's going to happen, having done this for years, is none of these, these products are just band Aids for when we can't do real world events. Right. They're band aids and they don't connect to the real world and they don't do the things. I mean you and I met. How many folks I've met at Sasser events, how many folks I've met on the road, they don't. It doesn't work.

Yeah.

And so there is, there is artificial demand because we can't meet in the real world and you can't charge $50,000 for a piece of software that doesn't do much more than have some Zoom streaming in it. Okay. So there will be a date of reckoning coming. But, but what I do think is I think folks like Hoppin and maybe a few others get it and we may have incredible software at the end of next year like to do things online. Event software has claimed it does collaboration since the dawn of time and it doesn't. Okay. It's a very expensive way to process tickets and registration. There are no collaboration tools. Right. And having one on one chat roulette with a random person of 10,000 is not fun. Okay, but what could be done with AI with other things could be amazing. So I'm very, I'm very negative on where these products are today. We use them all. It's Aster. But I'm really excited. We're 24, 24 months in the future with hundreds of millions of dollars being invested. Magical things can happen. Right. So I'm very excited about 2023 and 2022 for today and I'm very negative on where the software is today because we have too much, we have too much riding on it and nothing really works.

Yeah, yeah. So it sounds like you. So it's good to hear that. I think a lot of people in the audience would be comforted to know that at least the biggest, most, you know, famous event in our space is going to be coming back and you're going to be able to.

I think the big stuff will come back and whether smaller, it's like whether smaller stuff will come back remains to be seen. Whether will this kill the marginal get together? Probably with distributed teams, you know, it's probably going to kill the marginal thing because we're too many of us are working from home. Right. I think that's often what happens. Right. The best stuff can't be killed, but in tough times, the marginal stuff all just sort of fades away, doesn't it?

Yeah. Yeah. So true. Well, I hope it happens and I will be there. It'll be great to get out and just finally see people, you know, in person again, business wise. That just hasn't happened a long time.

All right, man, thanks for catching up. This was a lot of fun.

Likewise. Jason, any. Anything you want to promote, plug what's going on at Saster?

No, just, you know, just check out our blog once in a while. Saster.com that's all I need to plug. Come by every once in a while. That's all. Sign up for our newsletter okay.

Sign up for the newsletter saster.com follow Jason Lemkin Everywhere. He's always putting out good stuff. Quora. I love the Quora stuff. I, I hope people, if they're not following Jason on, on Quora, get on there. Hey man, it's been, it's been a good time. I appreciate the talk and let's stay in touch.

All right.

Thank you so much for listening to this episode of the Colin Kabmus podcast. Please don't forget this episode was brought to you by lessonly. Check out lessonly.com that's L E S-S O-N-L-Y.com this episode was also brought to you by spiff. Check out spiff.com forward/colin. Please don't forget to like, comment and subscribe. Thank you so much for listening and watching. And I'll see you next time.