Episode #85 17-Year Stay at Home Mom to $70M Tech CEO: How Elizabeth Andrew Built Her 4x4 Method

In this episode, we dive deep with Elizabeth Andrew, a seasoned technology CEO and five-time sales leader with a story of resilience and grit. After a 17-year career break as a stay at home mom, Elizabeth re-entered the workforce with zero tech experience and skyrocketed to lead revenue at powerhouse companies like HelloSign, Dropbox, Pluma, and Netomi.

We explore her 4x4 method for career transitions, the challenges of scaling sales teams, and why having a rock-solid sales playbook is non-negotiable. Whether you’re a founder, sales leader, or simply looking for inspiration, Elizabeth’s journey from stay-at-home mom to tech executive is a must-hear!

What You’ll Learn:
 • The four stages of building a successful go-to-market strategy: Stabilization, Foundation, Repeatability, Scalability
 • How to transition from founder-led sales to a scalable sales organization
 • Why most founders struggle with unrealistic expectations in sales
 • The secrets behind Elizabeth’s $70M sales playbook

🔗 Connect with Elizabeth Andrew: https://elizabethandrew.com
LinkedIn: https://www.linkedin.com/in/elizabethaandrew/

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Transcript

00:00 
This is Bridge the Gap, powered by Revenue Reimagined, the podcast where we dive into all things revenue. Each episode, we bring you the top founders and go-to-market leaders to challenge how you think about growth and help you bridge your biggest go-to-market gaps. 

00:14 
I'm Adam Jay. And I'm Dale Zwinski. As always, thanks for hanging with us. There's a million ways you could be spending your time and we're grateful you're choosing to spend it with us. Be sure to check out our newsletter if you want the show notes and tactical advice on how to bridge your GTM gaps. 

00:30 
Let's get to it after a quick word from our sponsor. 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. 

00:42 
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. 

00:56 
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. 

01:15 
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've heard of. HelloSign, Dropbox, Pluma, Netomi. She's the former co-founder of Sales Compete who now helps others navigate career transitions with her four-by-four method, which is a blueprint for building momentum, seizing opportunities, and something we all love, 

01:39 
creating new income streams. Elizabeth, welcome to the show. So great to be here. Thank you. I feel like we all as revenue leaders have connected on LinkedIn, and it's just so fun to get together in real conversations and excited to be here. 

01:57 
Awesome, thanks for joining the show. 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 Bridging the Gap is we go through four stages and we look at stages, stabilization, foundation building, 

02:25 
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. 

02:39 
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 the organization. 

02:58 
Yeah, great question. And this is my jam, Dale. I'll give you to kind of give. The first time you've ever had a good question. Let me give you just kind of the two-minute overview of kind of what got me into tech sales startups. 

03:16 
I am 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 Funds. I started doing corporate training and development, and I was giving presentations for stock brokers that would come in from all over the world and realized I could make a lot more money on the sales side. 

03:37 
And so I transitioned to sales. And when I was about 28, I was recruited onto the founding team of the very first mutual fund company for Wells Fargo Asset Management. The laws had changed, and banks had never been able to sell investment products before that. 

03:56 
So there were four of us, and we took that from zero to over a billion dollars in assets for Wells Fargo. And so I really learned, and I was young, they hired me. I built the inside sales organization from the ground up. 

04:09 
I mean, this was zero to one. It was ground up. And I learned from the best in the world, the top investments sellers in the world. And so literally, I spent a couple of years building this inside sales organization. 

04:23 
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. And so they asked me, knowing the product and having met at the company, to go open up that region. 

04:35 
So I moved literally in January to Boston from California, sight unseen in my late 20s, calling on stockbrokers. And I laughed, 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, white men that were older. 

04:56 
And I went from being the only woman in the room. 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? 

05:09 
And we know as sales leaders, that's really what it's all about, especially when you're starting ground up. And, you know, I was representing, I was a California girl representing a West Coast product in the mutual fund capital of the world. 

05:22 
And, you know, 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. 

05:33 
And I focused on building out this entire business plan, which was four, it was field sales, four meetings a day, four days a week. One day is your office day to follow up and always be scheduled two weeks out. 

05:45 
Speak in my language. Yeah, so, you know, this is the process, right? You have to build, right? Going from your, you know, more of your stabilization into that foundational piece, right? And, You know, so I learned how to build that process. 

05:58 
Always be scheduled two weeks out. You never wanna wake up Monday morning with nothing on your calendar, right? So it's like, you know, it was a very comprehensive playbook on how I was gonna tackle the region and everything. 

06:07 
But so, you know, 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. And I ended up marrying a New York Italian character. 

06:22 
And, you know, after a couple of years of building that Northeast region, I moved down to New York and left my career and decided I wanted to start a family. And I ended up becoming a 17-year stay-at-home mom. 

06:37 
And what's interesting about that is I'm not one of these people that can just play golf and, you know, I need to be doing something. So in the 17 years as a mom, and I was all in, I have three great kids. 

06:47 
In fact, my oldest is a SDR now. So, you know, the apple doesn't fall too far from the tree. But I did a ton of nonprofit work, a lot of fundraising. I raised over a million dollars for certain nonprofits and event planning. 

07:04 
In 2011, I was going through divorce, moved back to the Bay Area with my kids and had to go back, you know, 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. 

07:18 
And so my back was against the wall and 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. 

07:32 
I ended up finding my first job on Craigslist. But when I was, but here's the key is, and this is kind of flash forward to what I'm doing now. I asked myself, what did I do, you know, as an early 30-year-old to be successful? 

07:47 
And it went back to that business plan, that playbook. And so I created a sales play bit, for lack of a better term, for my job search. and returning to the workforce and I just treated it like I was building a company or building a startup or building a sales region you know I try I couldn't get any interviews but have four conversations and whether it's a networking event or you know whatever it is a day and and so so you know then I went on to become a three-time sales leader five time or five-time sales leader three-time VP of sales CEO and all those things that that you mentioned Adam so it's been really really a fun run I so you know I love I was not I ran the sales org 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 through I've been able to participate in three exits but I love those early stages I love the those you know taking a company through those four levels and then passing it off to somebody who's can take it further. 

08:55 
So that's a little bit about my background. I don't know if that even answered your question, Dale, but let me ask. So we talked about the four stages. And you've been a part of all four. We're big believers that they have to go sequentially, right? 

09:09 
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? 

09:25 
Is it stabilization to 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. 

09:49 
And if there are VCs involved, because you know what, I mean, we all know this as sales leaders, right? Unrealistic expectations. Right. I mean, I've worked for some genius, brilliant Silicon Valley CEOs. 

10:04 
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 that I respect that, you know, have far better education than I do. 

10:14 
But they all think the product's going to sell itself. And it never does. And they don't understand. Exactly. And I've, you know, I've actually in this conversation, I've never heard the four stages, the way you guys are spelling it out. 

10:29 
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 are building out, you know, a support system, whether it's your advisors 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 stage. 

10:58 
Well, there's some, there's some fluidity through those, right? You get a, like, there's not like, it's not like a single path either. Like we talked to a lot of companies, startups, founders. And the reason why we started our own business was because we would get pitched probably like you do, like we're investors. 

11:17 
Hey, we have a great funnel. Hey, there's tons of leads. Every customer is happy, products working. And then like you get inside the business and you're like, okay, there's a lot of broken pieces to this. 

11:27 
And if I knew it before, I would have had a different path or structure or like place where I would have brought you. But now we're here three months later and it's like, you know, you got to close business super quickly. 

11:39 
So one of the things that we've been working with with a lot of our, our founders and revenue leaders is like, let's take one step back to create three steps forward. And it does, it does allow them. 

11:52 
Some breathing room like if you're in there by yourself, you're the revenue leader, you got to build a 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? 

12:12 
Is it building the process? Is it stopping the bleeding? Is it coaching 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. 

12:25 
I'm doing a 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. And the first thing I do is audit, you know, is really audit the organization to understand where the pieces are really broken, right? 

12:46 
And you might have to go back to the very, very beginning and rewrite the whole book, rewrite the whole plan, you know, the strategy. And it takes, that takes some time. Like, you know, I know, 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? 

13:04 
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, you know, sales person in their organization to creating an organization to scale. 

13:21 
So I'm putting in that 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, that's such a critical piece is making sure that that infrastructure is in place. 

13:39 
Yeah, 100%. There's so many times like you touched on a couple things, right? VCs, I think, certainly changed the game with their expectation. having the infrastructure in place and transitioning from founder-led sales, I find that oftentimes founders wanna go right from founder-led sales to repeatability. 

14:02 
And it's like, oh, let's just go hire a full-time sales leader and they're gonna like fix the problem. How do you convince founders and for every founder listing, because that is the majority of our audience, that that's not the right approach or maybe you think it is the right approach? 

14:16 
I don't know. 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. 

14:29 
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14:40 
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14:57 
And so I really, and I've gotten, 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. 

15:13 
Like most of the Silicon Valley founders are most of it. This is a generalization, not all, but most of them come from either the technical or the product side. I'm sorry, I'm like having a little water. 

15:26 
The technical or the product side. And again, they think the product's gonna 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. 

15:39 
I think that's fair. They don't, you know, they think, you know, in general, I mean, they think that, you know, that sellers are all full of it. And, you know, and many of them have made their mistake their first or second or third by not following what you're talking about and not listening to their sales leaders or hiring the wrong sales leaders. 

16:00 
Maybe people are 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. 

16:20 
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 the, I think this is part of being a mom. 

16:32 
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, you know, organizations that'll be like, oh my God, this is a shit show. 

16:43 
And I'm like, I know, isn't that beautiful? Like this is the stuff that we all have to figure out and get all of those pieces in place. Yeah, yeah. I do think being a parent helps. I will just leave that there. 

17:01 
But I do think being a parent helps 100%. Yeah, you get you get to let them fail as well, right? I mean, we have, we have the things where like, we want to save everybody or like, we think we're gonna know best. 

17:14 
But, you know, this one of my best learners have come from reps that have had amazing success. And show different ways of calling or connecting or that type of work. Elizabeth, as you as you moved, I'm curious, as you transitioned from like a foundation process, you built everything out, you got nice playbooks running, where what was the challenge on unrepeatability? 

17:43 
Like, was it hiring the right people? Because I think salespeople are super hard to hire. Is it onboarding and coaching? Like where is the challenge once you gotta get all that foundational stuff laid and you're trying to scale the business, where do you find the biggest challenge there? 

17:59 
I think the talent management is a huge piece at that stage. You gotta 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? 

18:12 
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, you know, there's always gonna 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 gonna be happy about it. 

18:30 
And they're gonna 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. 

18:46 
They build the playbook. They roll it out once to the sales team and expect it's gonna be followed, right? It's just that it's gotta be the reinforcement and making sure it's the measuring and tracking. 

18:57 
Just go do this. Train, yeah. Okay, we did our discovery training. You got this, you know? And it's like, no, you gotta make sure you gotta 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. 

19:15 
You have to get on the calls. You've gotta be on the conversations with the team members and push up your sleeves and do the job shoulder to shoulder with them and teach them. Don't just tell them. Teach them and work with them and provide feedback. 

19:31 
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. 

19:42 
And I think they just saw that I had a breadth of experience and it was a healthcare tech company. I was the only person that. that hadn't come from healthcare. I learned so much in that role. I got up to speed on all the tools and whatnot. 

19:55 
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. Certainly when I was launching, Wall Street was demonized. 

20:09 
But you can learn the tools in six to 12 months. You can't teach 20 years of experience. And I love, it's like being a student of your profession. I love to learn. I mean, I love to learn. And when I started Hello, Sign, they took a risk on me. 

20:24 
I hadn't been in a sales role. I started as an IC. I hadn't been in a sales role in 20 years. I'd never sold SaaS. I was on a team of stereotypical SaaS sales dudes. And I learned so much and had so much fun with the team. 

20:39 
And I hope I taught them some things too. I really came from more of an enterprise. And background and, you know, this. was some of them are mostly transactional. And, you know, so it's it's constant learning. 

20:51 
And, you know, again, Adam, to your point, parent parenting, right? It is, it is parenting, I have to parent every day, it's very, very difficult process have to parent, you do have to every day. Yeah. 

21:09 
And it goes through, you know, if you take the talent management piece of the equation, it's almost like parenting ground up, right? You talk about throughout the four stages, right? Like, early on, you know, you have to you have to shut down the temper tantrums, if you've acquired some people, you've got to, you know, you've got to get them on board with the rules, you got to, you know, you got to do a lot more educating and teaching and training and telling them what to do. 

21:36 
And then as they get further along, you get more as more into kind of an advisory role, you know, and there's different different leaders have different perspectives on this, you know, and I've heard some people say like, I remember talking to one founder that I mean, he had had one of the biggest exits of all time years ago. 

21:56 
And, you know, he had this rule of five, like, you know, two, I can't remember if it was two or three reps will fail. So just cut them off, you know, shoot them as quickly as you can. That was that's not my strategy. 

22:10 
I'm a mom, like, I like to focus on like, get everybody trained, you know, the top producers, get out of their way and bring in your, you know, your weak links, you know, get them up to speed, and then you can, can really drive your numbers forward. 

22:29 
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 put the demo process out there and they're all gonna follow it. 

22:48 
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. 

23:15 
Oh, so when you go in and 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 like really build the foundation. 

23:30 
Or are you more in that, holy shit, we gotta stabilize this and fix everything that you broke because you don't know sales and go that route first. What do you see? I 100% say you have to go in and you got to start at the beginning, right because the founders I mean the founders and this is a couple 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 You know and to know if they can't sell it nobody can you know, 

24:03 
I've I've had I've had a lot of CEOs that They're building pretty cool things in theory, you know Like really sexy AI companies and things that are like we want to bring you in and have you built the whole sales Or if they are pre-revenue, they don't post a deal I'm like if you can't close it nobody can right like nobody's gonna understand the product as well as you can right? 

24:24 
But they usually don't and in fact, I worked for one CEO Pluma Alexandra Connell and we were acquired by skill soft and you know, that was a really it was 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 at say Oh, she was only VP of sales for a year and a half or something. 

24:48 
And well, we I knew When I was hired that we were gonna Be shopping it to sell it, you know, and but we had a we we had taken it from zero to eleven million. There was 20 people on the team in the US aside from the engineers. 

25:04 
We had no marketing no SDR team 11 or 12 of the 20 people were on my team. It was a hundred percent enterprise outbound sale 100% outbound and you know, it was it was great and I mean I remember Alexandra She's a Princeton undergrad and Harvard MBA She's you know, she's in her 30s. 

25:26 
She's just absolutely Incredibly dynamic and I remember after the company she said, you know, she said I Will never do enterprise sales as a startup Again, you know, it's hard It's hard You know, 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 the process. 

25:53 
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 built. Let me hear a little bit about your four by four methodology. 

26:09 
So you built on this four by four methodology, you know, in a couple of minutes, what is that? What's the four by four methodology that people can learn from? Yeah, I'm super excited about this, actually. 

26:23 
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 working for the man. I mean, I see my kids' friends and people are tired. 

26:34 
It's such a weird time. 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 four by four method based on what I was saying earlier, is I rebuilt my career by using a sales playbook. 

26:55 
And it's like diet and exercise. We all know what we need to do, right? But it's actually doing it. If you work out five days a week, cut out sugar, eat this and that and follow that, then you're gonna lose weight, right? 

27:07 
It's like you need to have a plan, a playbook. So the four by four method is Silicon Valley 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. 

27:20 
I actually just, this is insane because this has never been on my bucket list of things to do, but I just got invited to have an episode on my story on Legacy Makers Television, which will be streaming everywhere in next summer. 

27:35 
I just signed the contracts last night for that. So, but I'm really excited. I'm trying to get into more motivational speaking and inspiring people. I'm also working with bigger companies to the employee engagement is at an all time low. 

27:51 
I mean, employees are so disengaged and companies by following this four by four method can really help by supporting their employees in their own personal endeavors, right? Outside of the workforce and create more of a culture where people are not so dependent on the nine to five. 

28:13 
Yeah, so I am gonna be launching. If you go to elizabethandrew.com for backslash for meetings, I'm gonna be launching. a master mind starting on I think it's the 27th of this month so be fun awesome congratulations that's super cool thank you thank you let's uh as as we come up on time let's dive into some rapid fire which i know is dale's favorite part of the show um elizabeth early bird or night owl night owl if you were in tech where else would you be like what would you be doing motivational speaking 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 your foundational go-to-market ICP buying persona value proposition constantly it is it is a revolving book you should be reevaluating Is it monthly? 

29:21 
Is it monthly? Is it bi-annually? Is it annually? I feel like it's painting the Golden Gate Bridge. It's ongoing. You have to be revisiting and redeeming and revisiting and you just sort of never... It's not like... 

29:38 
And I think that's, again, that's where a lot of founders and sales leaders, they build this book, they roll it out to their sales team, they put it in Google Drive or your internal wiki or wherever it is and it sits there and collects dust. 

29:53 
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 is Bitch, but I have my money by Rihanna. 

30:21 
I like it. 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. 

30:41 
Very cool. We're sending you here to 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 elizabethandrew.com, right? 

30:56 
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 I look forward to continuing conversations for sure. 

31:08 
Love what you're doing. Thank you. Thanks so much for listening. We hope you enjoyed the conversation as much as we did. As we say at the end of every show, give more than you receive, reach out to someone today and offer your assistance. 

31:19 
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31:36 
Until next time.