17-Year Stay at Home Mom to $70M Tech CEO: How Elizabeth Andrew Built Her 4x4 Method

Let's face it, y'all. Hiring sales talent is a real pain in the ass. Getting A players is key to bridging your go-to-market gap, but it's harder than ever. If you're not actively engaging passive talent, you don't stand a damn chance. That's why at Revenue Reimagined, we trust our partners at Pursuit to help our clients find the best talent fast. If you're looking to strengthen your sales team, go check them out at PursuitSalesSolutions.com.

Welcome back to another episode of the Bridge the Gap podcast. We are stoked to have Elizabeth Andrew with us today. She's a seasoned technology CEO, five-time sales leader with a powerful story of resilience that we'll get into. After a 17-year career break, she broke into tech with no prior experience and went on to lead revenue at small little companies you might have heard of: HelloSign, Dropbox, Pluma, Nomi. She's the former co-founder of Sales Compete, who now helps others navigate career transitions with her 4x4 method, which is a blueprint for building momentum, seizing opportunities, and something we all love: creating new income streams.

Elizabeth, welcome to the show.

So great to be here. Thank you. I feel like, you know, we all as revenue leaders have connected on LinkedIn and it's just so fun to get together in real conversations, and I'm excited to be here.

Awesome. Thanks for joining the show and putting up with Adam. Although, the introductions are always the best part of the show.

Don't demean me. Dale, don't demean me.

Inside joke. Inside joke.

So as a sales leader, Elizabeth, one of the things we've been talking about and why we renamed our podcast Bridge the Gap is we go through four stages and we look at: stabilization, foundation building, repeatability, and scalability. And as a sales leader, I bet a lot of places you went into, you've had to stabilize everything. But whoever you're reporting up to, the CEO, they're like, "We want repeatable. We want scalable revenue." And you're like, "I can't get there from here."

So tell us a story on one of HelloSign or wherever you went in where you were like, "Let's take a step back and really stabilize our process and start building the foundation," so that the audience can know like this is something that has to happen every time a new sales leader comes into an organization.

Yeah, great question. And that's my jam, Dale. Let me give you, for the first time, a good question. Let me give you just kind of the two-minute overview of what got me into tech sales startups. I'm from the San Francisco Bay area, and I'm a little long in the tooth, particularly for tech. But I started out in the investment industry in the mutual fund space. I was at Franklin Fund. I started doing corporate training and development, and I was giving presentations for stockbrokers that would come in from all over the world, and realized I could make a lot more money on the sales side. So I transitioned to sales.

When I was about 28, I was recruited onto the founding team of the very first investment fund mutual fund company for Wells Fargo Asset Management. The laws had changed, and banks had never been able to sell investment products before that. So there were four of us, and we took that from zero to over a billion dollars in assets for Wells Fargo. I really learned, and you know, I was young. They hired me. I built the inside sales organization from the ground up. I mean, this was zero to one, you know, from the ground up.

I learned from the best in the world—the top investment sellers in the world. I literally spent a couple of years building this inside sales organization, and the last region we went into as an investment company is the Northeast because that's the investment capital of the world. The way the Bay Area used to be for tech, they asked me, knowing the product and having been at the company, to go open up that region. So I moved literally in January to Boston from California, sight unseen, in my late twenties, calling on stockbrokers.

I laugh because I literally went from being the only woman in the room. I mean, I'd be giving presentations for 500 Merrill Lynch brokers that all looked like my dad, you know, white men that were older. I went from being the only woman in the room in the investment industry to later being the oldest person in tech. But I learned a framework. I learned how to build playbooks. I learned how to build a business plan, right? And as sales leaders, that's really what it's all about, especially when you're starting from ground up.

I was representing a California girl representing a West Coast product in the mutual fund capital of the world. I just focused, even though I knew the product. I started outside of the city. I picked a few little towns, spent three months getting beat up and understanding the nature of the region. I focused on building out this entire business plan, which was: four field sales meetings a day, four days a week, one day is your office day to follow up. Always be scheduled two weeks out. Speaking my language, yeah. So this is the process, right, that you have to build, right? Going from your more stabilization into that foundational piece, right?

I learned how to build that process: always be scheduled two weeks out. You never want to wake up Monday morning with nothing on your calendar, right? It was a very comprehensive playbook on how I was going to tackle the region.

So I took that region single-handedly from zero to 70 million in assets, which was great. When I moved East, 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. After a couple of years of building that Northeast region, I moved down to New York and left my career. I decided I wanted to start a family, and I ended up becoming a 17-year stay-at-home mom.

What's interesting about that is I'm not one of these people that can just play golf. I need to be doing something. So in the 17 years as a mom, I was all in. I have three great kids. In fact, my oldest is an SDR now, so the apple doesn't fall too far from the tree.

I did a ton of nonprofit work, a lot of fundraising. I raised over a million dollars for certain nonprofits and event planning. In 2011, I was going through a divorce, moved back to the Bay Area with my kids, and had to figure out what to do. I walked away from my marriage, candidly, with nothing—no alimony, no child support, 100% care for my kids. My back was against the wall.

Nobody would talk to me. Absolutely nobody would talk to me. It wasn't until I took all my volunteer work, which was harder than anything I've done professionally, off my resume that I could even get an interview. I ended up finding my first job on Craigslist.

But here's the key, and this is kind of flashing forward to what I'm doing now: I asked myself, "What did I do as an early 30-year-old to be successful?" It went back to that business plan, that playbook. So I created a sales playbook, for lack of a better term, for my job search and returning to the workforce. I just treated it like I was building a company or building a startup or building a sales region. I couldn't get any interviews, but I had four conversations, whether it's a networking event or whatever it is, a day.

Then I went on to become a three-time sales leader, five-time sales leader, three-time VP of sales, CEO, and all those things that Adam mentioned. It's been really a fun run.

I was the sales manager at HelloSign when we were acquired by Dropbox, and I did that for about a year. But I've been able to participate in three exits. I love those early stages. I love taking a company through those four levels and then passing it off to somebody who can take it further.

So that's a little bit about my background. I don't know if that even answered your question, Dale, but let me ask: we talk about the four stages, and you've been a part of all four. We're big believers that they have to go sequentially, right? You can't go from stabilization to repeatability. You can't go from foundation to scalability. You have to go: stabilization, foundation, repeatability, scalability.

Looking at those crossovers, having been through all those stages, which in your opinion is the hardest? Is it stabilization of foundation? Foundation to repeatability? Or repeatability to scalability? And why?

I don't think that—I mean, I think they're all hard. I think really where a lot of it comes down to being challenging is really who that founder and CEO is and if there are VCs involved. Because you know what I mean? We all know this as sales leaders, right? Expectations, right? I mean, I've worked for some genius, brilliant Silicon Valley CEOs. I've been the only person on my leadership team that wasn't first generation Russian. I've been the only person on my leadership team that wasn't first generation Indian—brilliant people.

# Transcript

I respect that you know you have far better education than I do, but they all think the product is going to sell itself and it never does. And they don't understand. And I've, you know, actually until this conversation, I've never heard the four-stage the way you guys are spelling it out, but I agree 110%. I mean, it's just that's the reality of it, right? You can't put the cart before the horse. And so you know, I think a big part of being successful is having a leadership team or building out a support system, whether it's your advisers or your VCs or your CEO who's on board with making sure that each of the steps are handled before trying to move forward to the next.

Well, there's some fluidity through those, right? You gotta like, there's not like a single path either. Like we talk to a lot of companies, startups, founders, and the reason why we started our own business was because we would get pitch probably like you do as investors. Hey, we have a great funnel. Hey, there's tons of leads. Every customer's happy. Products work. And then like you get inside the business, you're like, okay, there's a lot of broken pieces to this. And if I knew before, I would have had a different path or structure or place where I would have brought you. But now we're here three months later, and it's like now you got to close business super quickly.

So one of the things that we've been working with with a lot of our founders and revenue leaders is like, let's take one step back to create three steps forward. And it does allow them some breathing room. Like if you're in there by yourself, you're the revenue leader. You get to build the process. You got to stop the bleeding. You got to close the business. And you got to coach all your sales reps. Like it's nearly impossible to do. And so if you have all these things that you're trying to do, what would be the first thing you would go after? Is it building the process? Is it stopping the bleeding? Is it pushing your reps? Like where would you start if you went in as a new revenue leader into an organization?

Yeah, well, interesting. I'm doing a lot of this right now. I stepped back after we sold Sales Compete about a year ago, and so I'm doing a lot of fractional sales leadership or fractional CRO work where I go in. The first thing I do is audit, you know, really audit the organization to understand where the pieces are really broken, right? And you might have to go back to the very beginning and rewrite the whole book, rewrite the whole plan, you know, the strategy. And it takes time. And that's one of the things that's really challenging for revenue leaders is that you know, it's hurry up and close, right? But you've got to get the infrastructure in place.

And I love what I'm doing now is I'm working with founders who are going from founder-led sales or maybe have a first or second sales person in their organization to creating an organization to scale. So I'm putting in that foundational piece. I'm starting at the first stage and putting in that foundational piece in order to take it forward. And you know, I think that's such a critical piece is making sure that infrastructure is in place.

And 100%, there's so many times like you touched on a couple things, right? VCs, I think certainly change the game with their expectation and having the infrastructure in place and transitioning from founder-led sales. I find that oftentimes founders want to go right from founder-led sales to repeatability. And it's like, oh, let's just go hire a full-time sales leader and they're gonna fix the problem. How do you convince founders? And for every founder listening because that is the majority of our audience, that that's not the right approach? Or or maybe you think it is the right approach. I don't know, but I certainly don't think it's the right approach. How do you convince founders to take a step back to take a step forward?

People buy from people. That's why companies who invest in meaningful connections win. The best part: gifting doesn't have to be expensive to drive results, just thoughtful. Soso's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process. Trust me, I led sales for a Soso competitor and I could tell you no one does gifting better than Soso. If you're looking for a proven way to win and retain more customers, visit Soso.com.

I mean, I'm in an interesting part now where I've done this enough. And so I really, and I've gotten, you know, I think we all learn, right? Like we've gotten ourselves in situations as revenue leaders where we don't have that full support. You know, and so I really, I won't work with any founders who haven't at least closed a few deals on their own.

Like most of the Silicon Valley founders or most of this is a generalization, not all, but most of them come from either the technical or the product side. They think the product's going to sell itself and they don't necessarily understand what is involved. They, with lack of a better term, they don't respect the sales function. I think that's fair. They think that in general, sellers are all full of it. And you know, many of them have made their mistake their first, second, or third by not following what you're talking about and not listening to their sales leaders or hiring the wrong sales leaders, maybe people not experienced to do this, right? They've been burnt.

You know, the biggest mistake that most founders make is their first sales hires or their first sales leaders. They either hire somebody too senior too soon, or they hire somebody to be a VP that doesn't know and understand these steps and foundations. So it's a lot of it is educating the founders on really understanding what it takes to build the business, right? And that's where I love this space. When I get into it, I think this is part of being a mom. I'm good at wearing a lot of hats. You know, and I can't even tell you how many people I've brought in or worked with in sales organizations or revenue organizations that'll be like, "Oh my God, this is a show." I'm like, I know, isn't that beautiful? Like this is the stuff that we all have to figure out and get all those pieces in place.

Yeah, it's I do think being a parent helps. I will just leave that there. But I do think being a parent helps. 100%. Yeah, you got to let them fail as well, right? I mean, we have these things where like we want to save everybody or like we think we're gonna know best. But you know, some of my best learning have come from reps that have had amazing success in showing different ways of calling or connecting or that type of work.

Elizabeth, as you transitioned from like a foundation process so you built everything out, you got nice playbooks running, where was the challenge on repeatability? Like was it hiring the right people? Because I think sales people are super hard to hire. Is it onboarding and coaching? Like where's the challenge once you kind of get all that foundational stuff laid and you're trying to scale the business? Where do you find the biggest challenge there?

I think the talent management is a huge piece at that stage. You got to get to the place, right? And it's like I feel like I could write a book on the difference between acquiring a team and hiring a team, right? And there's pluses and minuses on both. Right? And in most cases when you've got a sales leader coming in, there's a cross-section, right? You've got some. There's always going to be that seller that was there before you. If you acquire a team that thinks they should be in your role and they're not going to be happy about it, and they're going to give you a lot of resistance, right? But you need to get the team. And it doesn't matter necessarily. Like you need to invest in the team and educate the team and get them.

I think where a lot of people fall short is they build the whole infrastructure, they build the playbook, they roll it out once to the sales team and expect it's going to be followed, right? It's got to be reinforcement. And making sure it's the measuring and tracking, do this, train, yeah, okay, we did our discovery training, you got this. You know, and it's like no, you got to make sure. You got to get. And that's where I think a lot of it gets hard. A lot of sales leaders, you have to get, even if you're a CRO at this stage, you have to get in the weeds. You have to get on the calls. You've got to be on the conversations with the team members. And you know, push up your sleeves and do the job shoulder-to-shoulder with them and teach them, don't just tell them, you know? Teach them and work with them and provide feedback.

And one of my favorite things about this stage too, and this is one of the things that I've loved, I mean, I started my first job in tech. I finally landed a job at a healthcare tech company doing sales ops. And I think they just saw that I had a breadth of experience.

It was a healthcare tech company. I was the only person that hadn't come from healthcare. I learned so much in that role. You know, I got up to speed on all the tools and whatnot. And I think that's one of the reasons why a lot of people are hesitant—a lot of founders are hesitant to hire people that have a career gap or later in their career. You know, certainly when I was launching, Wall Street was demonized. But you know, you can learn the tools in six to twelve months. You can't teach twenty years of experience. And you know, I love being a student of your profession. I love to learn. When I started at HubSpot, they took a risk on me. I hadn't been in a sales world. I started as an IC. I hadn't been in a sales role in twenty years. I never sold SaaS. I was on a team of stereotypical SaaS sales dudes. And you know, I learned so much and had so much fun with the team. And you know, I hope I taught them some things too. I really come from more of an enterprise background. And you know, this was some of that but mostly transactional. And you know, so it's constant learning.

And you know, again Adam, to your point about parenting, right? It is parenting. I have to parent Adam every day. It's very, very difficult.

It's the process. You do have to parent me every day.

Yeah. And it goes through you know, if you take the talent management piece of the equation, it's almost like parenting from the ground up, right? You talk about this throughout the four stages. Right? Like early on, you have to shut down the temper tantrums. If you've acquired some people, you've got to get them on board with the rules. You gotta do a lot more educating and teaching and training and telling them what to do. And then as they get further along, you get more into kind of an advisory role. You know, there are different leaders that have different perspectives on this. And I've heard some people say—I remember talking to one founder that had one of the biggest exits of all time years ago—and you know, he had this rule of five. Like, you know, two or three reps will fail, so just cut them off as quickly as you can. That was not my strategy. I'm a mom. I like to focus on getting everybody trained. You know, the top producers get out of their way and bring up your weak links, you know, get them up to speed. And then you can really drive your numbers forward.

There's—I think the point I'm seeing over and over again is you have to have a system. You have to have a process. It's not as simple as "build it, they will come." Roll out a sales playbook and they will come. Put the demo process out there and they're all going to follow it. You know, it doesn't work that way. You have to have a process.

And I agree with you that most founders—few exceptions—are technical founders who don't know go-to-market. The best founders that I've worked with are the ones who recognize that they don't know go-to-market and trust the experts to do that.

Elizabeth, when you're doing a lot of founder-led sales transitions now, are you finding yourself starting more with "Hey, the founders are in a good spot. We can move and really build the foundation," or are you more in that "Holy, we got to stabilize this and fix everything that you broke because you don't know sales"? What are you seeing?

I one hundred percent say you have to go in and start at the beginning, right? Because the founders—and there are a couple of reasons why I will never work with a startup CEO or founder who hasn't closed deals on their own. One, they haven't realized how hard it is. And two, if they can't sell it, nobody can. You know, I've had a lot of CEOs that are building pretty cool things in theory—like really sexy AI companies—and things that are like, "We want to bring you in and have you build the whole sales org," or they're pre-revenue and want to close a deal. I'm like, if you can't close it, nobody can, right? Like, nobody's going to understand the product as well as you can. But they usually don't.

And in fact, I worked for one CEO, Pluma Alexander Cornell, and we were acquired by Skillsoft. And you know, that was really interesting. We went from four million to eleven million in a year. And you know, I was only VP of sales for—this is one of those experiences that you know you'd look and say, "Oh, she was only VP of sales for a year and a half or something." And well, we went from zero to eleven million. There were twenty people on the team in the US aside from the engineers. We had no marketing, no SDR team. Eleven or twelve of the twenty people were on my team. It was one hundred percent enterprise outbound sales. One hundred percent outbound. And you know, it was great. And I mean, I remember Alexandra—she is a Princeton undergrad and Harvard MBA. She's you know, in her thirties. She's just absolutely incredibly dynamic. And I remember after the company, she said, "You know, I will never do enterprise sales as a startup again." You know, it's hard.

And I think that's where, you know, usually the founders that have had success selling on their own didn't do it based on a process. You know, they did it. And that's why you need to come in and you've got to build that process so that you can repeat it with the rest of the sellers that you build.

I would love to hear a little bit about your 4x4 methodology. So you built out this 4x4 methodology. In a couple of minutes, what is that? What's the 4x4 methodology that people can learn from?

Yeah, I'm super excited about this actually. I'm kind of becoming unplugged. I think we're in an unprecedented time in the world, to be honest, where a lot of people are tired of working for the man. I mean, you know, I see my kids' friends, and you know, like, people are tired. It's such a weird time. People, even if they love their job, they want a side hustle or a passion project. People are trying to take their own control and goals into their own hands. And so I created the 4x4 method based on what I was saying earlier. You know, I rebuilt my career by using a sales playbook. And you know, it's like diet and exercise. We all know what we need to do, right? But it's actually doing it. You know, if you work out five days a week, cut out sugar, you know, eat this and that and follow that, then you're going to lose weight, right? It's like you need to have a plan, a playbook.

So the 4x4 method is Silicon Valley's secret to exponential growth for your personal and professional goals. And so I'm working with people. I'm starting a mastermind in a couple of weeks. I actually just got invited to have an episode on my story on Legacy Makers Television, which will be streaming everywhere next summer. I just signed the contracts last night for that. So you know, but I'm really excited. I'm trying to get into more motivational speaking and inspiring people. I'm also working with bigger companies. You know, the employee engagement is at an all-time low. I mean, employees are so disengaged. And you know, companies, by following this 4x4 method, can really help by supporting their employees in their own personal endeavors, right, outside of the workforce. And you know, create more of a culture where people are not so dependent on the nine-to-five.

So yeah, so I am going to be launching—if you go to elizabethandrew.com/4x4meetings, I'm going to be launching a mastermind starting on, I think, the twenty-seventh of this month. So be fun!

Awesome. Congratulations. That's super cool.

Thank you. Thank you.

Let's, as we come up on time, let's dive into some rapid fire. Which I know is Dale's favorite part of the show.

Elizabeth, early bird or night owl?

Night owl.

If you weren't in tech, where else would you be? Like, what would you be doing?

Motivational speaking. Ooh, love that one.

Where do you start first—marketing or sales?

Sales.

This is a big question I've been thinking about for a long time. How often should you revisit your foundational go-to-market ICP, buying persona, value proposition?

Constantly. It is a revolving book. You should be reevaluating all of it.

Is it monthly? Is it biannually? Is it annually?

I feel like it's painting the Golden Gate Bridge. It's ongoing. You have to be revisiting and tweaking and revisiting, and you know, you just sort of never—it's not like, and I think that's again where a lot...

Founders and sales leaders build this book, they roll it out to their sales team, they put it in Google Drive or your internal Wiki or whatever it is, and it sits there and collects dust.

Yeah.

What's the song that gets you in the zone for work? You're down, you're unfocused, and you just want to get in the zone for work.

Oh gosh, there's so many. It kind of depends on the genre. My latest—you want my latest? It's "Better Have My Money" by Rihanna. I like it.

Last one as we wrap up: dream vacation destination?

I had an opportunity last year to go to Necker Island with 30 entrepreneurs and Richard Branson. That was the most extraordinary place, and I want to go back.

Very cool. Very cool. Elizabeth, first time we heard Necker. Yeah. That is thank you so much for joining us. Thanks for walking us through your thoughts on bridging the go-to-market gap. And as you said, people can find you at elizabethaandrew.com, right?

Yes, and on LinkedIn—Elizabeth A Andrew.

Yeah, everyone on LinkedIn. Elizabeth, thank you so much.

Thank you, thank you guys. So great chatting with you, and look forward to continuing conversations for sure. Love what you're doing.

Thank you.