S4E7 - How to pick the right rocket for your moonshot

Hey, everybody, it is Richard Harris, the Scott lease with another episode of season four from Surf and Sales Podcast with a big shout out to the HubSpot Podcast Network for putting us on there. We appreciate their support and sponsorship. And you know, it's still raining here in Northern California. I might float away. Scott just told me he's sitting in sunny Austin where, What is it, 70 degrees on Scott?

I think it's more like the mid-60s. It's real rough out.

I was gonna say, do you need to put a sweater on?

So I probably do because, you know, I don't like cold weather, but you'd be fine.

I think now that you're getting older, I'm gonna send you a sweater with arm patches. Those brown arm patches.

Yeah. And buttons. Big buttons on my sweater too.

Yeah, exactly.

So like a grandpa.

Without any further ado, I want to introduce a good friend of mine. I've gotten to know Elizabeth for a while the last couple of years. It's Elizabeth Andrew. She's a three time VP of Sales. She's done TEDx speaking and had to exit. So really, really excited to talk to her and just sort of hear what she has to say. So, Elizabeth, welcome to Surf and Sales Podcast.

Thank you. It's great to be here. And as we were touching on before, I've had a chance to work a little bit with both of you and, you know, just, just super happy to be here. I also live very close to you, Richard. So we're being washed away here in Northern California.

Yes, we are definitely 100%, I don't know, gonna float away soon, I don't know. So we'll figure it out. So Elizabeth, just. Let's just go all the way back to the beginning for you. Oh, I have another good question we'll have to talk about, but like, how did you even get into sales? Like, as I've known you, like, you have this energy and pep and excitement about sales. You love it, you're passionate. Were you always that kid?

Yeah, you know, I have a very unusual background, Richard, as you know, for tech in particular. You know, I'm from the Bay, grew up in the Oakland East Bay area and started out in the investment industry. And, you know, it was a long time ago, but worked at Franklin Funds, ran a call center, moved into corporate training development, which I loved and I was good at and realized I could make a lot more money on the sales side. So that was really the first time I got into sales. Particularly, I didn't grow up, you know, with the lemonade Stands and all of that sort of thing. Although I did do quite a bit of leadership stuff in college and things like that. But.

But it was great. It was back when you know investment companies, it was sort of the wild wild west for investments and banks were able to sell their very first, actually very timely conversation because we were selling mortgage backed securities. Wells Fargo was looking to build their very first mutual fund company. The laws had changed and they hired me to come help them build an inside sales team. And it was very much of a startup. There were four of us. There was a national sales manager and two field salespeople and we took that from zero to a billion dollars in sales for Wells Fargo.

And I hired, trained and managed 15 inside salespeople not unlike a know an SDR BDR team which was super fun. And the last region we went into was the Northeast because that was the investment capital, you know, the world, the way the bay was in tech before the pandemic, which is now Austin as you know. Everybody's gone to see Scott.

And so I did, I moved out to the northeast side unseen in January, working out of my house in my car back when carrying a bag, was carrying a bag and I was calling on stockbrokers, Merrill Lynch, Smith Barney. So it was a, it was a challenge for sure. I was definitely the only woman in the room and took that from 0 to 70 million in sales.

So you think that today's modern seller would be able to do what you did?

No.

Tell me more about why.

I mean I think. Well, I think we're in an interesting time, Scott. Like I, you know, like listen, I've been through a lot of down markets, some long in the tooth and. Right. So I think in this kind market is when your talent really shines. You know, we've been in an environment for the last 15 years or at least less, you know, since I started out in tech, since 2011 where in some organizations all you need to be a top producer is to be up next in the rotation. You know, there was no such thing as marketing in those days. There was no such thing as an inbound funnel. And you know, we didn't have lead generation teams. There was no such thing as 90% inbound. I mean I opened, I was out there, I opened up what we called the red book, which is literally a phone book of investment firms and had to cold call and try to get appointments to go in and, and meet with their teams. And you know, it was, it was challenging. And the other thing is too, that I think is very Very different is in this day and age, buyers come to the market very different. You know, they come, they're 60% educated when they get into the conversation, you know, even if it's just googling before they have a meeting with, you know, an ae. And so we didn't have any of that either. So there was, you know, it was a lot more of educating and really having to build from the ground up, you know, that sales process.

Yeah, it sounds like that's the more traditional evangelical sale. Right. Like, you know, that's, that's what you would call that today where people didn't know, although I don't know that I believe that stat that people are 60% educated or even down the path. I think they're 60% down the path of curiosity.

So. But you know, it's a good quote. Everybody loves to repeat.

So yeah, I think it depends on the product and the organization too. And you know, that's not to say there isn't a lot of talent now and that there are people out there that work a lot harder. And you know, you do have to particularly enterprise. I come from enterprise. Even though I've led emerging teams, I've led mid market teams. You know, you have to do your research, you have to be able to navigate complex sales cycles, understand complex products, come in with different stakeholders. So you really have to do a lot of your homework. And I think the best, you know, of the technology salespeople obviously have done, have worked really hard as well.

When you shifted.

Because I actually just had a conversation. How long ago did you shift from sort of that traditional financial model to more of a SaaS software model?

When did you do that? How many? Like what year?

Yeah, so when I was transferred out east and I was young, you know, when I was transferred out there, my family said go for two years, have a great time, don't fall in love. I ended up marrying a New York Italian character and moving down to Manhattan and becoming a 17 year stay at home mom.

And sounds like you really listened to the advice. Well, yeah.

Right, yeah, exactly. Like, you know, who listens to their parents. Right. You know, and so I did. Yeah, I, you know, I decided I had taken that region from zero to 70 million. I wanted a family. I decided it was time to, to be home. And I'm actually one of those people too that doesn't, I need to be busy. I like to do things right. So it's like I was very involved. I was started out being involved in the schools, I was involved in nonprofits. I Did a ton of nonprofit work, raised fundraising. I did event planning. And all of that was harder than anything I've done professionally. You're dealing with volunteers. You can't fire them if they don't show up and don't do their work. And, you know, so it. It was. It was also a really interesting thing, too, because oftentimes, a lot of the people that I was doing a lot of volunteer work in those years were typically women that came out of big careers in New York. And so some of those. Those nonprofit organizations that I worked in were literally. I mean, I remember sitting in one meeting, and I was like, this. This group of people could plan the Battle of Normandy. You know, it was very well educated, smart, you know, hardworking people. And so it was interesting. I moved back here in 2011 with my family, decided my kids were getting a little older. It was time to get back to work. I found I was totally unemployable, could not get a job anywhere. And it wasn't until I took all of that volunteer work off my resume that anybody would even talk to me.

Why do you think that is? That's crazy.

That was. That was the big difference. So you think you went from unemployable to employable simply by removing all the volunteer work that you did?

Definitely not. No. It took a lot more than that. It took a lot more than that. But there is. And you guys have probably heard, you know, there's so much talk out there about women and women in leadership and women in tech, and there's the McKinsey study, the women in the workforce that comes out every year that they did in conjunction, I think it was, with Sheryl Sandberg a number of years ago, but they still put this out every year. And I remember reading something in there that said if you have two candidates with the exact same resume, exact same resume, and one has PTA coordinator on it, they're 70% less likely to get the job.

I didn't know that that is.

I do. I do think that's changing. I do think post pandemic, we're becoming a lot more open to. There seems to be a lot more empathy out there, and we seem to be a lot more open to diversity of backgrounds and people who've taken a break for whatever reason, you know, but certainly back then.

That was 2011, 2012, you know, 2015. That was definitely the case. Do you.

So was that first job coming back in tech? And the reason I'm asking is, you know, I hear this terrible excuse from Lee, from Candidates that they make it to the fifth round of interviews, and then they're told, oh, you don't have any tech experience. You're coming out of telecom or you're coming out of hr, you know, of recruiting. Just.

They couldn't figure that out in the first four conversations.

Right, exactly. So I'm curious if you ran into that and how did you sort of break through that to get into your tech side? Like, I'm trying to find that advice for people.

Yeah, absolutely. And, you know, so I actually ended up finding my first job on Craigslist, and I found it not in tech, but I found it at Putnam Investments, working for the west region director of sales who was based in San Francisco. And I was basically doing sales enablement for his wholesaling force. So I knew the space, and it got me in. Got me back into the city. You know, it. It got me at least learning how to do a calendar invite. I mean, I was literally back in the day planner. You know, like I. Kids. I remember one of my sons.

Sounds like you.

Yeah.

Do a calendar invite, Scott.

I'm quite good at calendars. Thanks, Richard.

But there was one time. I mean, literally, Scott, I remember when I was back in Connecticut and I was with three friends, and we were trying to schedule time to, I don't know, for a meeting or something, and they all had their iPhones, and I had my day planner, and my son was in class, and he could see me, and he was absolutely mortified.

You know, there's my mom with her big day planner, you know, I mean, it was crazy, but. Yeah, but so I did that at Putnam for about a year and just felt like there's no fun to be had in financial services. And so much going on in the bay in tech and so much energy. You know, as long as I'm reinventing myself, why not trade tech? So. So I did. And. And to answer your question, I think.

You know, I. The big argument that I say is that you can teach the tools. It's true. I mean, a lot of companies say, hey, you know, they're. They're out of date with the tools. Tech tools.

Yeah.

You can teach that in six to 12 months. You can't teach 20 years of leadership experience in.

Did you feel like you had to reinvent the way that you sold and learn a new kind of methodology of. Of selling, of prospecting, of delivering value and finding pain and then even of closing?

So I. Yes and no. I learned when I moved east, I was trained by. We had a really good team I mean, they were like the top. Some of these salespeople, wholesalers were making 10, 15 million a year commissions, right? So I was trained by some really, really successful sales, individual contributors. And I was taught, you know, before I moved out to. To Boston, I was taught. We called it a business plan. It was a playbook, right? So you just set up those repeatable processes. You have four meetings a day, four days a week in person, and then one day is. Is your office day. You always are scheduled two weeks out. You know, it's the who, you know, creating, repeat, repeatable process. And, you know, I. Even though I had been at the company for a couple years, I didn't start selling. I didn't go into Merrill lynch, downtown Boston. You only get one shot there, you know, so I started outside the city in some little small towns to get kicked around for three months. And, you know, and. And I think I shared with both of you. I mean, I literally would. I was giving meetings for 500 people, and I'd be the only woman in the room. They were literally all white men that look like my dad, you know, And, I mean, I remember one point, I was quoting the Wall Street Journal, and some heckler in the back is like, what journal? The Ladies Home Journal.

Wow.

You know, it was. And I popped off right back at him. And. And that office ended up doing a lot of business for me because, you know, I was able to.

I want to know what you said.

You know, it's, It's, It's. It was easy to get in the door. It was very difficult to establish credibility, you know, and so I love.

So, so slowing it down there, right? So it's. How do you. How do you have to establish that credibility as a woman? Right. You do walk into this room with 10, 20, you know, 500 men, right?

Yeah.

Because I don't know what that's like to have to establish that credibility. And my guess is you could probably more the same advice maybe into any gender or ethnicity, right. Where you're not the white guy in the room. What have you learned to help.

Yourself and others?

I see it as an opportunity, of course, that day and age, too, nobody was talking about diversity. Certainly weren't talking about the rise of the woman leader or, you know, none of that was even a conversation. Right. So, you know, I just, I see it as an opportunity. And, you know, I. I think the best way to establish credibility is to really know your stuff.

And really, that was my question. So it is part of it is a mindset when you're facing an uphill battle in general, but, you know, I could see myself having an imposter syndrome like before I go into that meeting or something. So what are the things you tell yourself? What advice would you tell another person who has to get that mindset shift?

Yeah.

You know, I think again, I think, you know, and I use that, that repeatable process and everything I've done, like getting even, just getting a job, getting back to work. You know, I was talking to Scott about like getting my next VP of sales roles. Like you want X number of opportunities in the pipeline at every time. Right. So I just focus on the activities and not try not to focus on the intimidation. I, you know, I kind of, there's two, two ways I look at it. I, you know, I, my dad, I think I shared. You played in the Rose bowl for Cal. I have two older brothers. Like I'm thick skinned. I mean, you know, I'm, I'm thick skinned. But, you know, you learn pretty quickly. Like who.

Who can you educate and have similar values with and who do you just need to walk away from and get away, you know, and turn away from? And it was, you know, that was, it was also an interesting time too because it wasn't just me going out break groundbreak. I mean, it was from the ground up that we never had anybody out there. This is a west coast bank. This was Wells Fargo Asset Management. It was their Overland Express funds that we were selling in the biggest community of, you know, Putnam, Fidelity, State street, you know, all of those east coast companies. So it was a company that was a little different too.

That wasn't as well known. But you know, I think you just, it might be, some of that might be inherent too. It's just, you know, it might be a skill to just. I love to take on a challenge.

Yeah, I, I having known you, I know that about you. Like, I know you don't walk away from things and I don't know that, that, I think that was taught way before you ever even had a career. Right. Like that was to your point.

Yeah. And I, you know, I had the same thing in tech. I mean, it was, it was not. There were so many people in tech that wouldn't, you know, I'm learning more about the community and the older community that's been around in the mid teens, you know, and, but you've got an.

Incredibly good picker, for lack of a better phrase. You picked the right companies when you were back east. And Richard said at the beginning of the show you've had Two exits. So you've not only done well yourself, but you've somehow identified companies that are going places, products that are going places, teams and I would imagine team cultures even that are doing things the right way. Most people go their whole career with no exits. You've had two. How are you picking the right horse so frequently?

In most.

One of the hardest things, I think.

That there is, it is, it is one of the hardest things and it's one of those things that I've struggled every time and, and you know, some of them haven't been the right horse. I mean, I will tell you, you know, sometimes you just take what you can get. You know I, I joined, I was really lucky to get a job. It was funny because I had done inside sales, external sales, sales training and development and sales leadership in my early career. I found my first job in tech in sales ops and of course not knowing the tools. You know, it was a healthcare tech company. I was actually, I know they hired me because of my experience and my sales enablement. It was awesome for me because I had to self teach myself all the tools and I joined right before. It was like the God Summer of 2014 maybe I forget but I joined and then I went to Dreamforce and I just parked myself at the genius bar, demoed every product on the expo floor and just learned as much as I possibly could. So that was really good. But, but that company, you know, I learned a lot. And it's funny because I think a lot of people when they go to hire and I think VP of sales is probably the hardest role right in, in startups.

The hardest role to do or the hardest role to hire for?

Maybe both. But I think, you know, if you're in a publicly traded company and you don't hit revenue numbers, they fire the CEO. In a hyper growth or a startup, it's the VP of sales. Right. So there's a lot of pressure on that CEO.

It's usually the founder.

Yeah. And the founders and you know, I mean you could, you guys probably know better than I do. The data of turnover of you know, first vps of sales is, it's, it's not great, you know, and.

You know, it's, it's a challenging role.

Let's talk a little bit more about the actual exit because we don't get to talk to that many people who've gone through it.

What are a couple things that are, are big positives having gone through an exit and what are a couple things that are distinct negatives? What are the Things people should be looking out for.

Yeah, so I was.

I think people have an unrealistic view of exits.

You know, you're not a billionaire yet, right?

Like I think people, you know, the people that are not tied to it or have not been through it think, you know, it's, it's going to be a game changer. And no career ending. It's not. I mean one of them, I was VP of sales. The other I was just in sales leadership. But.

You know, it's.

So there's a few different levels to the like financial impact of an exit. There's the, what I call buy a new car level. It's like the Nissan Leaf level. Congrats. You can buy yourself like a thirty thousand dollar car. Then there's the level where you make six figures and it's like, okay, depending on where you live, you could put a down payment on a house. Then there's like you actually cracked seven figures. And that for most people is a significant milestone that can make a really big impact on your, your life, your current life. It doesn't really set you up for the rest of your life. You sure as hell are not retiring for that. And then there's this whole other threshold where you've achieved fuck you money that very, very few people get to in a VP of sales kind of role. And I think everybody automatically assumes, oh, Elizabeth has two exits. She was a VP of sales, she's at that you money level. But that's not really the reality.

No, not all. And I'll tell you a couple of things. First of all too, I mean this is a personal level too. Like everybody's got their own stuff, right? But like I was married 21 years. I walked away for whatever reason and we had been hit with 0708 and you know, that wasn't part of it. There were other things that led to that, but I walked away with full custody, my three kids and no money. Like literally like I could have been homeless if I didn't have some family and friends that helped me a little bit in, in the early days, I would have been homeless. And you know, so I've like, like one of them, you know, it, it wasn't a car, it was my daughter's college tuition. But hey, I'll take that. You know, it covered.

But it's that level though, right?

Right?

Yeah.

Yeah.

Was that in state tuition or out of state tuition?

She's graduating Gonzaga this year, so that's good. Yeah, yeah, yeah.

So, but what are some, what are some of the Practical negatives and downsides. Richard's company just acquired Elizabeth Country. Country company. Like, what should people be expecting to have happen?

Yeah, well, so it's interesting. Two things to answer. First of all, you know, I'd rather be lucky than good. When you were talking about picking the right horse, you know that. That healthcare tech company ran out of funding, went bankrupt. I found myself at a job search and I found hello Sign through Angelist. And that was. I was talking to somebody the other day. I was there for four and a half years and I was talking to somebody that said, hey. It kind of seemed like that hello Sign team was kind of a cult. I mean, we just had a very tight knit. You know, it wasn't always perfect, but, you know, we had. It was a good run. I was about employee number 40 there. That's really where I learned a ton. I started as an ic, moved into leadership. We were acquired by Dropbox. And that was really probably the best experience that I've had that whole four and a half years because they were both Y combinator companies. I really learned the scaffolding and the infrastructure to build a successful organization. And so that's. That's been really great. When we were acquired, you know, I think, to answer your question, it depends a lot on who's acquiring you. I like an acquired. Being acquired is like having a stroke. You don't want to have one, but some are better than others.

Wow.

I've never heard that before.

I've not heard that one.

No.

No. All right.

You know, it's very, you know, you think, okay, yay. I gotta. I got a good check. And now it's like, how do we get these two companies together? And it can be very painful.

You know, that was the. They were similar cultures. But I mean, as I was leading the sales team and right after the acquisition, the VP of sales left. So I was really running all of them through the integration, reporting to Whitbow, who had come from box until.

You know, for the first nine or 10 months, until we started reporting up through the Dropbox sales. Org. But, you know, I don't know if you knew anything about Dropbox in San Francisco. If you guys. Did either of you go to that office? No, they had the tuck shop, which was the Michelin star chef with three meals a day. We had the vending machines where you badge and get the tech.

I couldn't keep myself 20 other companies like that.

Yeah, yeah. You know, it was that typical, like all the bells and whistles and I. I mean, my. I could not get my sales team to stay in. In their chairs. They were having so much fun running around the office. It was insane.

You know, yoga in the middle of the afternoon.

This is Scott's worst nightmare.

Yeah, but my next. The next one was a company called Pluma. Pluma was totally opposite. It was a bootstrapped company. We were 19 people in the U.S. we were about 80 in total. But a lot of them were engineers in India. Twelve of them belonged to me in sales. This was a VP of sales role. We had no marketing, no SDR, BDR team. So it was a 100% outbound enterprise motion. I joined there in late 2020 and literally got an offer and started an hour later because the. The CEO, Alexander Connell, who's brilliant, she was leaving in three weeks to have her first baby. And so I started right away. I spent that time at the end of 2020, you know, doing. Breaking down all the sales processes, rewriting all of that up, putting in new sales stages, training the team. We hit the ground running in January.

It was actually a really good run because on 100 outbound enterprise, we sold Amazon, Adobe, Gap, Sephora, Dropbox. We went from 4 million to 11 million in less than a year.

But what ended up happening there is Alexander Connell came back in mid January and she said, I just had my first baby. I don't want to work 100 hours a week anymore as a founder. I want to sell the company. So, you know, I had only been there like six weeks and, you know, I was like, no, you know, I wanted to stay, but I couldn't get mad at her. I made the same decision when I had my kids.

So I want to go back to the hello sign thing. So you talk about getting acquired, right? And the things that, you know, one of the things you notice for both those companies coming out of Y Combinator, and I love what you said, you said there was the scaffolding that was there. So if I'm interviewing at a company, whether they come out of Y Combinator or not, what kind of scaffolding am I looking for? What am I trying to uncover? Yeah, scaffolding. To see if it's going to be the right kind of company.

Yeah, yeah, that's a really good question. And, you know, I'm digging a lot more into those to understand, like, what is in place than I had in the past with financial stability and everything right now. But, you know, I think a lot of it just comes down to the mechanics, like, what is your sales methodology? You know, I've used Medic in all of mine. You know I've been trained in, I trained the team at Dropbox, we had in, in house training, we did Sandler training and you know all the different methodologies but.

You know it's breaking down the sales stages in Salesforce and understanding exactly what the entry and exit criteria are for each stage of that so that you know you're making really clear cut decisions on how you're moving things through the pipeline.

You know, I, the forecasting model, you know what kind of forecasting process and I actually learned a ton from. So after I, I led the whole sales Org reporting to Whit Balc or at least the sales teams reporting to Whitbock after the acquisition until the fall of. We were acquired in like January of 2019 I think it was. And then in the fall we started reporting up through a guy named Jaco who was most recently the VP of sales at Airbase. Great guy. In fact I'm going to talk to him later this week and he taught me a lot too and I only worked for him for maybe four months. He's just a great guy and it was just taking all of our processes and just putting them on steroids. So really more robust.

And I love this, I love the fact that you're asking, well tell me about your sales process and tell me about your sales training and your sales coaching and all those kind of things. Like those are things I encourage people to ask. Was there anything in the scaffolding around looking at the leadership team right when you were looking at hello sign of like, okay, is this the kind of leader I'm looking for? Any, any thoughts around that?

You know, not it, not at that time, no. I mean I was just grateful to have a job. You know, I say that the co founders there, Joseph Walla and Neil Amera invested a lot in culture. We had a really big HR team. In fact there was one point I was laughing, I remember sitting there and I was. We didn't have a sales, we didn't have any sales engineering but there were four people arranging cupcakes, you know, for the, for the.

Some celebration organizer is, is definitely something to look for in the scaffolding.

So yeah, yeah, I mean we had really. They invested a lot in culture and I think it, you know, it paid off for sure. I mean, you know, it wasn't always perfect. I mean they never are. You know, people bump heads and all this kind of stuff. But in hindsight we're all just very.

Close and yeah, Scott used to always tell me we should have a cupcake organizer, but I just didn't believe. So I'm glad to know you've reiterated his belief system.

So, yeah, another thing, you ignored me.

On exactly one of 20.

But I do, to answer your question, Richard too. I think that I've since come to the conclusion that the person that you report to is the single most important thing in your success or your failure.

I wonder if that is great. The single person, the person you report to is the single most important thing in your success or failure. I hope people listen to that.

That is, I think, in any role.

Yeah, I agree. I mean, it's. Look, it's just like, you know, hopefully when we try to find our partners in life, we find that person who's got our back. Don't always work out. Jobs don't always work out. But it's the same thought process. So we need to move over to sort of wrapping it up. And Elizabeth will give you a second to think of a question or two you want to ask us. But before we do that, just a quick shout out to HubSpot for supporting the Surf and Sales podcast and reminder that the Surf and Sales event is in November is still coming up. And we are. We discussed the dates yesterday. We haven't. I don't know if Jeff put them up on the website.

We've got them. They're not on the website, but we've got them locked and loaded.

Yes. So, Elizabeth, you've been saying you're coming. You've been saying you're even going to send your son to Surface. So it's time. It's time to, you know, work on the other stuff first. But yeah, it's time.

Yeah, send me those November dates. My daughter's graduating the weekend of it, of the May event, but send me the November dates. I'd love to go. And I'd love to have my son as an sdr, as I told you guys. So. Yep.

Yeah. So what do you want to ask us? Any questions we can help you with?

What do you think is the biggest piece of advice you would give moving forward in this market?

To what person slash role.

For tech sales leaders.

All right.

You'Re going to have to go all the way back to basics of sales. You're going to have to understand how to prospect the company and not the role. Meaning you apply, you find who you think the hiring manager is, linked in with them or email them. If you find their name or do both, you then find someone in hr. I'm not opposed to going after the CEO And I've even said, go after the board members. Hey, you're on the board. Board members are particularly people at the executive startup world. Board members want to know where good leaders are. And I think that it's often an overlooked spot. But I think you apply to that whole company, five or six people, and I think you also pick up the phone and call them, even if it's a bone tree. And that's my biggest advice. And I think a lot of, I mean, it's the same advice I give any salesperson, but I think it's a really important piece to, to focus on the whole, the company as a whole. That you're looking for.

Another. Another question for you too is that I, and this has been one of the things that I've learned, right, like, and it's interesting and I'd love to get your perspective. This could be. Probably go on for a long time. But like, I have decided in sales and I've worked for a lot of people that are Harvard, mit, Princeton, you know, Stanford, Cal in sales. I like people who are comfortable with failure. I want the kid that was cut from the team. I want somebody who was rejected from the college of their dreams. I love hiring. I've gotten a lot of success hiring out of San Francisco State. Gotten a lot of success hiring out of Chico. And you know, to that extent, like, I've also, in my experience.

I find myself defending some of my shorter VP of sales stints. And yet those have been some of the biggest learnings for me.

You know, I've, I've, I've learned a ton from what not to do. Even, even in that healthcare tech company that went bankrupt. You know, you learn a lot about, almost learn more about what not to do than what is going smoothly. And I'd love to kind of get your thoughts on that. And if you've had that experience in.

Any particular role.

That'S Scott, 100% go for it.

Well, I had the experience once, so I was, for context, I was a sales leader six different times. Five of those times I lasted between two and a half and three years.

And that's, you know, double the average.

Right.

One of those times I shanked and I was there for, I don't know, eight or nine months. I don't even remember the exact amount of time, but I do know that it was longer than I should have been there because I realized very early on, like, oh, I up and I screwed up because the product isn't ready. The leadership team doesn't make decisions. This thing Moves at a turtle's pace. Lots of different kind of reasons. So moving forward, I just owned it. And I just told the story as I screwed up. I was super successful the first time, was super successful the second time, and kind of thought, like, I could do anything and I didn't vet, you know, hard enough, and I'm not going to make that mistake again.

And. And then I just would kind of pivot the conversation to be more about me interviewing them.

And so I didn't go into, like, tons and tons of detail. I just sort of said, here's what I learned. I gotta bet this, I gotta bet that, and I'm not gonna make that mistake again, period.

So that's how. That's how I thought about it. And. And, you know, for me, for whatever reason, that seemed to work well. Now I don't have multiple super short stints. Yeah, one. I don't know if that played a big part of it or not, but I think owning it and talking about what went wrong with clarity, what you learned from it with clarity, and what you intend to do to prevent it from happening again, I think that's your best bet.

Yeah. And what, and what. What questions did you ask to prevent that from happening again?

Well, I should be asking you. I mean, you've got it right a few times in a. In a really nice way, you know, you got it wrong a few times.

Sure.

I don't know who's got the better batting average here, but, you know, I spent time digging into the product much more making sure that it worked, for example, testing it, playing around with it, that kind of thing.

I made sure that the founder had actually sold the thing. And when I before didn't care about that whatsoever, that was a big deal. I did a little bit more digging into who the people were specifically. Like, is this a founder who has already made a billion dollars and doesn't really care that much anymore, or is this somebody who's hustling and grinding, you know, for their first big win? I dug in a little bit more to who my peers would be on the executive team, if there was any. I dug a lot more into the amount of autonomy that I would have to make certain decisions and do them my way and build my team a particular way. I cared a lot more about those kind of things and dug into those more than I had done previously.

I think that's a really. That's really critical right now for anybody too. You know, like, even asking questions about, which I've never done before in, in sales leadership is really digging into, you know, what's your nrr, are your customers happy, you know, that sort of thing. Because it's a. It's a dicey time.

Yeah.

Yeah. I think. I think that's the growth we're seeing in the sales world in general. Like, we finally know how to ask some of these questions, you know, And I think it's also. As sales ops and revenue ops finally sort of have become more commonplace, people actually have that data. They're becoming more data interested and have that data and understand it. So I agree. It's the right evolution of asking those questions.

You know, are you. I'm curious, are you asking also because someone's bringing up these things as you've had conversations in the last, you know, years and stuff, or is it. You're just.

Yeah, I mean, I just. I'm in a similar situation that Scott's describing there, is that I am not making some of the mistakes I made in the past. I'm determined not to make some of the mistakes that I've made. And you've learned, you know, you learn from those. And, you know, some of them, I mean, I had three that weren't. Not super long, but one of them I joined in February 2020. I mean, that was.

Right.

That was that.

It's interesting, too, because if people are bringing up that stuff in your interview and they're not paying attention to the exits, then that to me tells me something about their leadership, you know, not that they shouldn't say, well, what have you learned? And those kind of things, but that's. It always makes me interesting that people love to go negative even though they don't think they are.

Yep.

But, Elizabeth, it is awesome to see you. We need to shut this one down for today, but it's great to see you. And I know we'll go do coffee again somewhere in the La Mirinda area when we get our boats out.

Yeah, exactly. We'll water ski over. Love to do that. So great talking to both of you guys. Thank you for your time so much. Elizabeth, chatting soon. Yep.