Jason's AMA on Building Top Teams in SaaS

Hey Jason, thank you and team for an amazing event. First time, we're really awesome. So I really follow your tweets and your content and you're like, I really love all the materials you guys put out there but sometimes you're like, I see the title, you know, like something like after 100 million ARR growth slows down. I'm like, dude, I'm trying to survive here, you know, super early. And like, you know, there's really a lot of other issues that I'm really concerned about that are not 100 million arrangements. So what are maybe like one or two things maybe you want to I think give as an advice to founders who are doing sales in very early stage. The first couple of million ARR maybe that you felt, you know, like are super. I think useful in that stage, in kind of like trying to develop that. I think that that sales muscle, if you will, within.

Well, look, first of all it's a good, it's good, some good feedback. We all the early Sasser content was only around folks sort of for like 1 to 5 million and we added more diversity to stages than others. And I think we've organized that we could better organize it. So it's good feedback to us, to our team to make sure there's an easy way that you can only get that content. And I've done some good videos and other content. But if you wanted me to distill like a couple pieces of advice that are most important, post one one to five something in that zone. Right? It probably goes back to so much of our iconic piece. First of all, and some of this was like really innovative years ago and now is table stakes and copied. But first of all, do whatever it takes to get 2 reps hitting quota. Whatever it takes, get 2 reps to hit quota. You'll never scale revenue if you can't get two people to hit quota. If you don't have two, who do you hire? This is the number one hack. I've had this conversation like 20 times here. Why did your first rep not work out? I always know the answer. Would you have bought from her or him? No. Why did you hire them? Well, they went, they. I liked their LinkedIn. They knew how to talk about ACV and MRR and RRM and. But would you have bought from him? No, I would not have brought a product. This is why we screw up. You can have when you hire your first couple reps, they do need to have sold a software product and vaguely similar, something at least vaguely close to your acv. Like they can't have sold pool equipment or, or plastic. Sometimes people hire that. It can work out a little bit for tiny SMBs, but it doesn't work in software, okay? Because there's a playbook at 3k ACV and 10k and 25k and 100k and they just know how to talk to customers and they know the cadence. So hire two reps close to your ACV and then forget all the other crap you read. Talk with them if you want, have them sell you this pen. Even if you think it's right, listen to them, have them do a zoom pitch. But then say, would I buy from him or her? And every CEO you talk to, almost everyone will have what I've written about and called the first magical sales rep. And when I first wrote this on LinkedIn, I got like 100 comments with everyone telling me who their magical sales rep to. I say they're a little quirky, they're a little smarter than usual, they're more product focused, they deeply understand the product and the customers frigging love that magical sales rep. Right? They often came from a slightly different place. That was mine too. Mine was an opera singer. He had come from a failed SaaS company and was mid pack at best. But his parents were both doctors. He was wicked smart and he friggin loved Adobe Sign and Echo Sign. He loved, he knew the ins. Was he the best closer? No, he was mid pack but. And I remember like the first Dreamforce I went to in sf. I'm walking out of the parking garage and this really tall guy grabs me by the back of my jacket. It's like Jason, like, he's like, you work for Echo Sign? I'm like, yeah, I work for, I'm one of the founders work for Echo Sign. It's grabbing me like this tall six, six sales guy, he's like, do you work with Joe Coletti? The sales guy's like, I work with Joe. Yeah, he's our only rep. Yeah, I work with Joe. I love Joe. I love Joe. And that's the kind of thing that you want. And you get that when you would buy from them, when you would buy from them. So find two reps you would buy from, work with them, help them so they hit quota and then hire a sales leader. The other mistake people make, I mean, it's become so trite. But the last panel I'm sure will recite it like it's hyper risky to hire ahead of sales, even a stretch one, before you have two reps that hit quota because ahead of sales job is to hire Reps 3 through 300. Not to create product market fit, not to create the playbook, but to take a really rough playbook and that it's not really clear why it's working. But you've proven twice two reps can hit quota. A smart first time VP of sales will listen, they'll learn, they'll get on calls, they may carry a quota, they may carry a bag and they'll hire you 300. So two you would buy from then wait, then hire the head of sales. Right? And then the last one then we could break. We go along is and I wrote this so early and people still think it's controversial today, but I wrote one of the first Saster posts and I've updated it which is I hired my VP of marketing at 20k MRR. It wasn't a week too early. Okay, I used to have like cuter titles but I hired it 20K. Mr. It wasn't a week too early. And I, and I went through the math. I hired, I hired Loretta at 20K. I didn't know much about marketing at the time but I think we went from like 2020, so 20k Mr. 240 to maybe 800 in a year. It wasn't like a rocket ship. Right? But you come in and all she had to do was help get me enough leads to close another couple hundred thousand dollars and that one more than covered her computer. Two fueled the sales team. Three built our bones so we could do more demand gen and things. And so don't hire someone that works on your logo all day. There's another old classic Saster post. Don't hire the wrong VP of marketer. You'll just get a bunch of pens with your blue logos on it. Half the folks here will tell you their mis hire of marketing just did like branding and product marketing and corporate marketing. No, but you can't hire a growth marketer, a true demand gen marketer, you can hire them too early when you have no customers. But as soon as you have even a hand 10, 20 customers, you can hire a great senior growth marketer, demand gen to get you more leads. So hire that person as early as you can find her or him. That's the third of the things. I distill it all down but thanks for the question.

Thank you so much.

Really appreciate it. Thanks a lot for sure.

Hey Jason, thanks for a great event.

Thanks for coming.

You recently wrote an article that said when the phone rings, pick it up. Even though the current DNA has put People in a work cycle and schedule any meeting in three days. Two part question, what motivated you to write the article? The other is, what's your advice to companies who want to change that DNA but are struggling with it?

Well, yeah, look, the irony is it's funny. Support is so. I'm so passionate about support for a whole bunch of reasons. But I got passionate about it initially because back in the day when I was the CEO, we quickly expanded to the UK very, very early. Like six months in, our biggest three customers were in London. Six months in, not expected. Right. A white swan event, maybe not a black swan event. And we had nine people and no one really was willing to do support from 12 to 6 in the morning. But our product went down every day, so someone had to do support when the load hit. And we went from like 10 concurrent users to 1,000 when this huge company rolled us out. So I mean you could imagine why there were issues. And so someone had to do support. And, and so I did it every night from 12 to 5 in the morning until we could do it for UK time. So I became very passionate about support tools doing this, me not having to do it. And so I got very early. I immediately, when I realized I couldn't hire 10 support people, I immediately hired an outsourced team in Canada so that someone could do the chat and pick up the phone 24 7. I figured out how to get good at that. And then I just kept investing in companies that did some of this because I was passionate about it. I invested in Talkdesk, which is worth 10 billion now, to do phone contact center. I invested a small amount in front, which is 1.7. I invested in Gorgias, which has 10,000 customers in the Shopify ecosystem. I invested in Meister QA, which is the leader in Contact Center QA making agents perform sort of like Gong, but for qa. And so I'm very passionate about it. But to really answer your question, why am I more passionate, it's because all of these SaaS, companies in support and outside of that invest in. No one does support. Even support companies do shitty support. And I go on, and I go on to all the leaders, okay, do all the leaders in SAS do the Zendesk and the Intercoms and do they answer their phone? And s none of them do either. Right? And I learned as a founder I could make up so many competitive gaps by picking up the phone. So many because no one did. And you can't solve a number one feature gap. But boy, when I had Someone, even when we were tiny, 10 people, 24, seven answering the phone. And I wrote them a script. So the top 10 questions, even if they. They couldn't do tier 2 support, right? But they could answer the 10 questions and they could say, I'm sorry, Bob, I'm sorry, Linda Scott, or someone will get back to you in a little while. Here's the best I know. Like, that didn't solve their problem, but boy, they felt better. Boy, our MPS was happier. And I'm just shocked, shocked. When SaaS companies say they can't afford to do support, they can't afford to do phone support. I'm like, I get it. But like, when I call the restaurant in San Mateo, they answer the phone. Why can't you answer the phone when all the restaurants at Saster Night answer the phone? Well, no, you don't need your top engineer answering the phone to have a human being. And it's the same. Half the questions are the same damn questions again and again and again. Do you have a HubSpot integration? Yes. I mean, whatever. Or like the Internet, the app doesn't work. Well, whatever. I mean, I'm not doing the best answers, but I'm passionate about it because I find so many folks in support crappy at smart. I'll tell you a last story. Obviously, I love HubSpot to death. I love everything about Brian and Dharmesh and the company. And there's no but. But I remember when they were kind enough to invite me to their founder day in 2019, and they did a whole thing on support. It was great. And they all talked about how they're going to automate support more and more. And I said, that's great because you have so many customers. Like, but I'm curious, how quickly do you pick up the phone? And they didn't know, Right? And I get that it's hard, but anyhow, I know you're in the space. We could end the question there. But I just think the reason I write it is because I've seen it myself and I've seen support. You gotta be good at whatever you do, right? And support companies struggle. But it's the simplest thing you can do. This next week, after all of the annual, is you can go back and you can upgrade your support. You can upgrade. You do not need the world's experts. You can outsource it to start. You can just hire one more person to pick up the phone. And if you're like, well, I'm going to get too many calls, well, at least you're going to answer some of them, right? And the other complaint we get is, hey, if I do real time support or if I do real time tickets, all my free users and my small users overwhelm us. Well, at least you can talk to some and then you can build systems and then you can filter the questions and then you can triage support and then you can hire someone just to do free and someone to just like at HubSpot just to do 2 to 20 and then just to do. There are tools, the systems and routing is much more sophisticated today. But even if you don't ship another feature this year, you can go back and you can upgrade your support next week and you can do some of it next week and you can do it over four to six weeks and your MPS will go up, your sales will go up a little bit, your NRR will go up and people will just be happier when as a human being, why do I have to spend this money and I can't talk to a person like it's criminal? Why can't I talk to a human being at any SaaS company? Why? I mean, we're switching to HubSpot because I love HubSpot. We pay Marketo like $100,000 a year. I can't get anybody on the phone. I tried to. I was using a product, a mission critical product for Saster over the weekend that went down. Okay. It happens. I go onto their live chat, they're like, response, we'll get back to you within a few days. Like, you're not down anymore. You were down. I have a question. I have to wait three days. How many of you can go onto your intercom or drift or whatever you use and it's going to say, someone will be back to you in 60 seconds. None of you. Right? It's criminal. And. And as expensive as it is, and I will end my rant or my ramble, whatever you think it costs. It's cheaper than engineers and it's easier to source than engineers and it's cheaper than building features and it's cheaper than building products. And it's not just that great support wins. That's of course hopefully true. It's that it's an upgrade. It's an upgrade you can do without a line of code, without another, without a VP of sales, without that great VP of marketing you've been spending a year to find you can do the upgrade at some level next week. So thanks for the question.

Thank you.

Yeah.

Hi, Jason. Thank you so much for putting this together. I Just want to give a shout out to thank you so much for taking in diversity inclusion efforts at Saster.

Thanks for coming.

Yeah, it was, it was wonderful to sort of be a part of it. So my name is Zoya and we are basically a gifting company. And my question to you is, so what advice do you have for bootstrapped companies that have just under a million but are having trouble sort of selling their mission, their story to investors?

Well, okay, I'm going to give, I'm going to answer. Let me break it up into two points. I don't think I'll give them the smaller point and the large point. I don't think you're struggling for investors because you're bootstrapped. Investors prefer. Actually, if anyone thinks investors don't prefer bootstrap companies, you're wrong. And every investor wants to do what Excel did in Atlassian. Atlassian bootstrapped its way up to like 50 million, 100 million, 100 million in revenue. And you couldn't get this deal today. I think it was 100 million. There's an old video I did with Jay Simons who was president then, I think at 100 million, Excel invested at 400. So four times revenue. And I think bought a quarter of the company. Okay. That's the best deal as a VC because there's no one else on the cap table. There's no. You're not jockeying with Sequoia and Andreessen for space. Everyone wants to invest in this. I talked to the first one I got here right when I walked into Sasser Square Park. We have a meet to CVC program and I talked to a bootstrap founder. He's like, jason, I love your me to VC program. I'm like, great. But some people have different experiences. Like I got 32 meetings already. I'm like, what's going on? He's like, well, I'm at 4 million. ARR. I'm bootstrapped. I'm going 150% a year and I'm in a really hot space. Well, you kind of get the meeting, right? So I just want to simplify. It's not. VCs prefer bootstrap companies. Yeah, you want signals. YC is great that we talked about that first round, did the precede. But fuck that. What they want is hot companies with room on the cap table where they can buy every share they want. So don't let that be an excuse. Don't. Bootstrapping is not. Bootstrapping is a reason. It's harder. Right. We'll get to that next but it's not, it is a positive for most investors. VCs would love to be the first one on the captain because there's more space and less drama. Right. It's what you want. The different point is bootstrapping is harder. And I asked Ben Chestnut from mailchimp if you were selling session and we, I, I didn't but we asked Michael Cannon Brooks from Atlassian and everyone says the same thing. I wrote this post a long time ago. It typically takes three to four years longer being bootstrapped. It does. And sometimes that can kill you if you pick the wrong part of a fast moving segment because someone will get funded and there are spaces, there's parts of FinTech payments where there's no time to bootstrap. Right. There are other niche spaces, maybe you vertical SaaS where you know it's competitive but like you're competing with 20 year old software. Like sometimes it's okay if it takes a little longer but how are you get there by 10? Here's the last point by it takes longer but by 10 million or so in ARR you have convergent evolution. These paths converge by 10 million ARR. If you bootstrap to 10 million ARR, you're generating enough cash to hire all the VPs you want. Okay. You can't hire a thousand sales reps, like maybe a Brex or someone can, but you can hire enough. You're generating enough cash at 10 million that you do. It is only elective if you want to control your future. Right? So the painful but best advice I can give to bootstrappers is if you're unable to get funding and you want funding and it sucks. And it does suck. It may be brutal, it may be painful, but by 10 million you may be Ben Chestnut. When they finally, after Constant Contact went public, they finally came to him and said Ben, can we invest in you? He's like I don't need your why would I take money now? Like I'm gonna just own all of it at 12 billion and you're not. You probably won't exit for 12 billion but it does normalize at 10 million so you got to brute force it to there. Right. So thanks for the question.

Thank you so much.

Hi Jason.

Hi. Thanks for coming.

Right, right before me. Thank you for the diversity program. Very grateful to be here and great to see a lot of different faces. So I think that makes it a better event and congratulations on 10 years.

Thank you.

And that's actually where my question comes from because you said at the beginning you were very focused on everyone learning from your failures and mistakes and then got into best practices. So we all know as entrepreneurs, once you hit a goal, it's really important to have the next one.

Yep.

Otherwise you're going to be like, okay, I got it, so what do I do now? So that's my question for you. I mean, what do you see as the next big thing that you want to achieve either with this event or the brand? How do you reach more founders? How do you help more people?

I'm just curious to know for sas for itself.

Yes. Or if you have personal goals also. You're like, now that I've done this for 10 years.

No, it's a good question. I think that we don't have it all figured out. Basically what we really want to do is do more types of mentorship and learning at scale. So, you know, if you did it, you know we did. We'd do like almost 2000 brain dates here. We got pretty good at it here. We got pretty good in Europe. We want to start doing that every week online. A version of it online, which hopefully we can roll out in Q4. There's different places that can go, but, like, maybe it's too niche. I mean, Saster is a community. It's not an event, it's a community. And we started doing meetups for a community because I'd never been to a meetup, but I heard people did it. So we did one and like 500 people came to the first. And that's common today, but it was unusual in business software back then. And those events got bigger, those meetups got bigger and became events and then became 10,000 people at events. But it's not about events, it's about what a sort of self organizing community. We're not forcing people to go on circle or discord. So it's a weird community in some ways. But how can you add value for the community? So the real goal is to add one minor and one major piece of value to the community each year and to grow. To grow with it. So I know it sounds a little amorphous. Saster itself, you know, basically has broke barely. Well, it lost money. It lost 10 million last year. Broke even as a side. Almost everything's free, right? All the contents free. Sasser University, thank you. But to fund operations, we do have, for our internal team, we do have a goal of getting it to 100 million. So SAS took a long time, but we'll do 27 million this year. Still give away Almost everything for free. It's not. It's kind of fun to give away everything for free and do 27 million, right? So our goal, tactically and for fun too, is to see if we can get from 27 to 100. Because 100 is a fun, a fun outcome, right? And if you're at 27, it's like, so it's kind of fun because, like, now we know how to get to 40 next year, it's like we know we can go from 27 to 40. Bootstrapped in a way, right. Even though I Invest, it's bootstrapped 27 to 40. We don't know how to get to 100, but we have hints of 100 and so kind of redoing that journey. But that's secondary to investing in the community. If we invest in the community, the rest of the stuff with good people just kind of. I don't mean to exaggerate, but it almost takes care of itself, right? Because these sponsors here, who we are grateful to, right, they're here, they're not diluting your performance. We're not selling out. But they want to be where number one is, right? So if we keep just add value, we'll get more sponsors and make it fun without having to like dilute our mission or anything.

There you go.

Thank you.

Thanks for the question.

Hey, Jason, this is Anthony from Deselect. And I'm sure you're fed up from hearing thank you by now.

Thanks for coming.

We implement like 80% of your content, so being here at Saster for the first time was quite transformational. So thank you.

Thank you.

I got two questions. First question is like a little more personal founder related, potentially cultural. What would you recommend a early stage founder who recently, let's say last Saturday, relocated to the US as a European to further scale his company?

What do I recommend?

Well.

Look, when I started investing, I did almost all euro to us, right? The first one was pipedrive, Estonia to the Bay Area. The second one was Algolia, France to the Bay Area. The third one was Talk Desk, which was Lisbon to the Bay Area. Right. And then I did a bunch of others. But that's a generation ago, right? That was a generation ago, but. And some things have changed, especially now that we're running distributed teams. Right. But what hasn't changed is that the ones that got the most out of it, and then I did like Showpad from Belgium.

Yes, they visited us. I know them.

What's that? Yeah, and some got more out of it than others. And I know this is totally obvious. So I don't know that I have brilliant advice here, but you got to. You got to like, network and you got to meet the Americans. Okay. And. And sometimes I invest in so many French. To us. Gorgeous. Plato, Algolia, Front vox E. I mean, a long list of others. And the French entrepreneurs, There's a great B2B ecosystem. Right. Especially technical, but they do hang out a lot together. Okay. And I'm glad the French have each other here and that they still come to the Bay Area since it's much further than New York. But you've got to meet other people. And too many founders end up coming to the US and mostly hanging out with somewhat similar founders. And I get it. And I think that's okay for peer CEOs, like, because you need peers. But it sucks for VPs, right? If you're from France, you don't want to meet the French VPs of sales that happen to be in the beer. You want to meet all the other ones and sometimes they're too insular. And I'm a little bit of an introvert. I thought Brian Halligan was the most extroverted sales guy. He considers himself an introvert. Dharmesh considers himself an introvert. But you got to just network, right?

Well, maybe on that note, we're still hiring a sales leader for Austin Office.

Yeah, Austin. And you got to hustle. You just got it. That's the thing. And so if you're going to move here today where it's. It absolutely helps. Right? But it's not as critical as it used to be. It's not. It's not like do or die like your world will end if you're a European founder and you don't come to the Bay Area. Like, your company will die. Like, we don't think that anymore. Right. Just make sure you get the bang for your buck because it is expensive on the soft cost side. I just don't go to every event, meet every VC network, go to every. Even if you don't like to do more of it. And you know, I'm the world's worst networker. I don't even know how to network. I don't know how to go to par. I mean, you heard Dharmesh's story. His wife does the networking for me. I'm kind of like that, except I don't have the partner to do it for me. I don't know what. I literally don't know what to do at a cocktail party. So one of the reasons I started Saster was so I'd have something to talk to people at at parties because I would go to like parties with like the dads at school and people would make fun of me because I didn't talk like, you know, I like be like how's your sales team going? They wouldn't want to talk about sports or like the core curriculum. So I know it sounds silly, but I wasn't good at it. So I formed a community to talk about SaaS. But force yourself, get taught. And what the. Sorry, I got a little on tangent. What I've learned doing this for 10 years is this shit compounds. These were the people you meet here today, a few of them. Most of them won't fail because very few people come to Saster that are pre revenue and almost no one comes before a million in revenue. So the people you meet today, you will meet a couple incredible people here that will go on and you will turn around. I didn't even know until I did a digital event with them that the founders of Monday came here for like their first US event from Israel. I didn't even know they came. And I checked by email. They sent me an email. I never met them. They're like dear Jace, whatever they're called before Monday, would you like to meet? Would you like to invest? I didn't even respond. That was a mistake. There's others. But a rambly point of you don't the Monday guys, they'll be here, right? And so don't just come to Saster. Do everything you can when you're local to do that. Because this person you meet here, that in a year, if they bond with them even a little bit, they may recommend a VP of sales to you in a year. Like these, even recruiting takes years over time. Right. And the executives you have today, you may need different ones in three to four years. And so these connections are so especially if you're like me and you're not inherently hypersocial, these relationships can become. You don't even have to force them. They can become so valuable over time. Right. So rambly answer is get off the YouTube and network until you want to throw up in the local community. Right.

All right, fantastic.

Thank you.

And if you have a hard time networking, I'm happy to have a drink.

Ok. Thank you.

I did have one more question.

I was exaggerating a little bit, but not too much.

Yeah, I have one more question. Say in today's market, your early stage and a bunch of great VCs are actually willing to give you money at Say a happy valuation, but you don't really need it.

Yes.

Are there any conditions you would still take that money?

Well, okay, look. Yes. Let me step back for a minute. The rough rule as you scale over time is only raise money if you need it, or it's cheap if you need it and you're lucky enough to get it, of course, take it. Right? Both of my startups at the time, I did not have enough personal resources to fund what they did, so I needed venture capital both times. The first time I got the World War deal, I raised eight on two. Do the math. Eight on two, what's the post?

Oh, is that a real question?

Yeah, 10. So how much did you sell in the first round?

25%?

80%? No, I raised 8 on a 2. Pre bad times, but I needed. But I needed it, Right. It didn't even bother me for a moment because the company wouldn't exist without eight on two. Right. That was like the lowest point in the history of fundraising. But we could chat about it later if it's fun, but. Or if someone else wants to ask. I'm happy to talk about it, but. And then the second time I needed less money, but I still needed it. So you needed your raise. Right. And then for me it was probably a mistake, but once I was profitable, even the second time, I stopped raising because I didn't need the money. Right. And if I hadn't, we hadn't sold to Adobe, I probably would have later raised when it got cheap, right? So if you need it, it doesn't matter because you need it. And if it's cheap, if it's cheap, then like there are reasons to not take cheap money, but you should at least think about it, right? Okay. So you're not in that you're doing okay. People want to fund you, but it's like you might sell 20 or 30% of your company now for some good money, but not a life changing amount of money for the company. That's the question, right?

Well, different numbers.

Enough, but not enough to change. Like it's enough, but it's not $100 million tomorrow, right? For 1% of the company. So notwithstanding the heuristic of cheap or whatever, I think that you, if you can raise money but you don't need it, you need to calmly take your time and say, who are the executives over the next 18 months, the VPs that I can calmly hire with this money? Because that's when you get the bang for your buck. And you have to ask yourself, am I a sequential hire? Do I hire a VP of Sales and then marketing and then Eng and then product and cs. Can I hire in parallel with this money? That's worth it. If you can find the people, it's worth it to hire in parallel. Am I too nervous? Did I turn away that VP of Sales candidate because she wanted a 600k OT? No. 600k sounds like a lot, right? But actually, when I think back on it, it was 250, but 350. So 250 base, but 350 if she hit the plant. And 250 base is only 20k a month, isn't it? So it's not that much if she performs because she raises the money or if she doesn't, I'm only at 20k a month. But if you're too lean, you think, oh my God, 600k OTE. I'm getting ripped off. I only make 80. And this VV of sales wants. So you got to think calmly. It's not just how would you spend the money? Because you'll come to the wrong answer. It's just the VPs. What? Because this is all about. Once you hit even a million in revenue, it's all about who you can recruit. Right. Before that, it's your founding team and it's. And so if you. If raising this money de stresses a couple critical VPs, raise it tomorrow. Right? That's. That's the answer.

All right, Great answer.

Thanks for the question.

Hi, Jason. My question's about the VP of Sales. Yes, We're. We're a company that's. We have two reps. They're going way over quota.

Okay, well, you're there, right? Yeah.

We follow your advice quite seriously, to be honest. Okay, so we're about to hire our first VP of Sales.

Okay, good timing.

And what do you think we should watch out for in the next 90 days? And when should we bring in our VP of Customer Success?

Well, those are two. What should you watch out for while you're hiring the VP of Sales?

No, once we bring them in. What should we watch out for?

Look, what you should. And I'll tell you, I'll give you a similar answer for success. Next. What you should watch out for when you hire a VP of sales, you will know before she or he starts. And I know I've written about this, and I know it's now become trite, but it's so true. Will they bring one or two good people with them? Right. A real VP of Sales. You know, this is old school. Not old it's not dated, but it's one of the first stuff I wrote, and I've written it probably a hundred times. What's the number? The number one job for a VP of sales is recruiting, is building a team. You have two. So whether her job is to get you from 3 to 10 or 3 to 6 or 3 to 300, it's recruiting. Recruiting's hard, right? Anyone think recruiting is easy in this room? Like, congrats to you, but it's hard, right? And so the best, even stretch VPs of sales, even, they're really just directors or leaders. They're always recruiting. They're always, they're always meeting people, recruiting. You know, I'm going to, in my next gig, I'm going to get Tony to run the West. I'm going to get Linda to run this. And they always have. They're always recruiting. And if they're more senior, they're always recruiting directors and VPs, and otherwise they're recruiting ICs. They're like, okay, well, at my last gig at Air Call, I worked with Joe. He was the best. I'm going to, like, I'm always with Joe. I'm getting drinks with Joe when I'm in town. Because when I do my next role or when I'm finally VP of sales the first time, I want Joe to be the first person on my team and I want Sarah to be the second. And so even if they're a stretch VP, even if they're, this might be their first VP role, if they don't have one or two queued up, 0% approaching 0% chance they make it okay if they tell you. And so I always ask, where are you going to get your first couple reps? And they're like, well, I'm going to hire some recruiters. We all need recruiters. I love recruiters. But when you don't have anybody, it's the biggest red flag there is. Even worse is, okay, what recruiter you're going to use. I'm not sure. Okay, if you're a great recruiter yourself, one, you recruit yourself. And two, you use recruiters to help. You have to use both, right? And so the best VPs of sales also have a recruiter they work with in some fashion, right? Even if they don't love them. And so point being, if they haven't told you who those people are, they probably don't have them. And you can talk to them and interview them and see the motion before they even start. And if you cut those corners and sometimes we do. You will know within 30 days whether they're on the job. And then we could talk. It's so true. But like let's imagine how much are you doing? A million in revenue?

5.

5 for two reps. Good job. Okay, so your VP of Sales job is to take you from 5 to 10, right? Or whatever. But let's call it 5 to 10. To keep the math simple, let's say you, obviously you've been wildly efficient, okay? But let's say you decide calmly, okay? Our reps can do like 800k to a million each. You're probably a little bit more enterprise or I don't know the story, but anyhow. Okay, what's that?

50K per rep.

Okay, so, but like you're gonna need to go from 5 to 10. Let's say it's 500k per each. You're gonna need 10 scaled reps, aren't you?

Yeah.

To go from 5 to 10. So the best VP of sales is really okay, that means I need four in my first quarter. And that means I need. Two is not enough. I need two more of my first month. And so they're always doing that. And so you see this motion and you see one of three things. When the VP of sales starts, you either see no motion in people. That's the worst sign of all. You see them bring in two or three folks they worked with before. That's the great sign. Or sometimes they bring in a bunch of crappy people, which is risky, but at least they're trying. But always, always ask them, who will you bring with you? And more experience, they might know 10. If it's really a stretch, I would settle for one. I know it's not enough, but the best ones always somehow bring their ringer. They bring their ringer one way or another. And like on our little sales team at Saster, Brian, our VP of sales, he brought in his old boss. One of his ringers was he convinced his old boss to come in and be one of our top sales folks, right? And so that's just another way to get it done, isn't it? But he did it right. But none of those like just no matter how much you like them, no matter how good they look in the blazer, no matter how much they talk the talk and tell you what it was like at GitHub or Twilio or what you just. Okay, great. Hooray, hooray. You're tall, strapping, handsome and worked wherever. Who you bringing with you? Who you bringing with you? And if you Get a mushy answer just and anyhow that's my rambling answer of even if you don't listen to me, even if you make the mistake Anyway, if 30 days in there's no one they haven't brought in any good like you need. It's not a black swan event but it's like a micro event you need to already be planning. As tragic as it sounds that they're not going to work out and you know we everyone talks about, you know hiring slowly and firing quickly. There's some toxicity in that, right? It's not more that, it's more everyone will tell you that gets on stage here that made a mishire in VP will tell you it's not just that they should have gotten rid of them quicker, it's the damage they do. The damage they do to your they spend all the money and they hire 10 terrible people and so give them severance. Friggin Give them a year of severance if you can. Who cares what the severance is. Move out. If they don't have Anyone good in 30 days, realize by day 60 you may need to move them out as painful as it is. Right? And then the last rambly point is the big mistake then they make is they don't talk to the two reps, they don't see the progress and they give them more time. Right? You can be a human being and it's not this this lame fire people. It's admit to the VP you hired. It's your fault. That terrible VP of sales you hired may well go on to a better environment and thrive. That VP of Sales maybe should not join a 5 million AR company but will thrive at a 50 million dollar AR company with a brand behind them or a 40 million dollar company with money or in a different industry. It is your fault as CEO if you hire a bad vp. Read more Saster it's your do not I blamed my first VP of sales. I blamed him for coming from Salesforce and never working at a startup and failing. I blamed him and it was not his fault. It was my fault for hiring him. It was my fault for sticking with him for nine months. That's all. 100. I thought it was like 50 50. No it was 100% on me. Right? So move them out by day 60. Apologize honestly say it was your fault. Give them a check if you can afford it. Give them a bigger check than you think they deserve. If you can afford. If you think they deserve 30 days, give them 60. Like treat people the way you would like to be treated, but address it honestly, take the blame and move on. So that, that's just what you want to do it between 30 and 60. Right. It doesn't mean don't back them. You gotta back your hires. Right. But if they don't bring in anybody, it's hopeless to go from five to 10, right?

Yeah.

Okay, rambly. Hopefully there's enough in there to be helpful.

That was really helpful. Thank you. Can I ask about the VP of customer success?

Oh yeah, real quick then we'll do one more. But look, I've written stuff like when the ideal time to hire VP customer success is. But the real truth is you're too late. At 5 million, you have too many. How many customers do you have?

Well, we have self serve and enterprise. Yeah, but about 22,000 in total.

And you don't have a VP of customers. So you know it's too late. Yeah, you know it's too late, right? Yeah, you can hack it with self serve and support and other things. But like the real issue today. So look, you can't actually hire a head of customer success too early per se. Here's the problem in today's world, right, which has changed is so many folks aren't willing to do any work anymore. The problem used to be everybody wanted to be senior. But now most VPs, you know, even five years, 10 years ago, a VP would come in and actually do sales or do support or do marketing themselves or set UP HubSpot themselves. Ten years ago, five years ago, they would do a little bit of it and hire them. Today everyone wants eight people. Everyone that has three years of experience wants eight people on their team. Okay, I'm a marketing manager here. I'll be your vp, but I need a head of content. I need a head of demand gen, I need a head of growth. What are you going to do? So the real problem with customer success is finding someone that will will do any work themselves these days. And that can mean different things, different functionalities. The problem in CS is folks that won't do the work all want to do process and systems. Now you will get big enough in CS where everyone knows your brand and everyone knows your product and your CS team do not have to be product experts. It's true. It's a weird moment in time when they don't have to be product experts. But usually Even up to 20 million ARR, your CS team have to be product savants. They're fixing feature gaps, they're tweaking things that don't quite work. They're doing hidden settings. They're fixing your admin tool. They're finding this rogue consultant that kind of gets you to integrate with HubSpot when it doesn't quite work. They're fixing a web hook or an API call that's sort of undocumented. And the best ones are these gurus, right? They're gurus of your product. And when you hire a 2 senior VP, they just want to install software and hire a team, and it just fails. So that's who you can afford. You're not big enough yet. Right. So. But make the hire, but make sure they're a product person today. Right?

Got it. Thank you so much, Jason.

Thank you. Good. All good. Okay. Thanks, everybody. Thanks for coming. I think we have happy hour till six.