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

Elizabeth Andrew's journey is a masterclass in resilience and process. After building an inside sales organization from zero to over a billion dollars for Wells Fargo in her twenties, she took a 17-year career break to raise her children. Following a divorce that left her with nothing, she applied a rigorous "4x4" sales playbook to her job search, successfully breaking into tech sales. She went on to become a five-time sales leader, fractional CRO, and CEO, navigating multiple successful exits including HelloSign's acquisition by Dropbox. In this episode, Elizabeth breaks down the harsh realities of scaling revenue. She emphasizes the necessity of moving sequentially through the four stages of sales growth: stabilization, foundation, repeatability, and scalability. Too often, pressure from venture capitalists and over-eager technical founders pushes companies to skip the foundational steps, expecting the product to sell itself or assuming a newly hired VP of Sales will magically fix a broken infrastructure. Elizabeth also sheds light on the friction between founders and incoming revenue leaders. She insists that founders must close their own early deals to respect the sales function and truly understand their market. For incoming sales leaders, she advocates for auditing the current organization, stopping the bleeding, and understanding that rolling out a playbook is useless without constant reinforcement, tracking, and measurement.

Discussed in this episode

Applying a disciplined 4x4 sales cadence to job hunting after a 17-year career gap.
Scaling Wells Fargo's first inside mutual fund sales organization to over $1 billion.
Moving sequentially through stabilization, foundation, repeatability, and scalability.
Why technical founders mistakenly believe a great product will sell itself.
The dangers of VC pressure pushing startups from founder-led sales directly to repeatability.
Why founders must close early deals themselves before bringing in a sales leader.
Taking a step back to audit a broken sales infrastructure before pushing for closed business.
The inherent friction between acquiring an existing sales team versus hiring a brand new one.

Episode highlights

0:00 — Podcast intro and hiring sales talent
1:30 — Elizabeth's background and 17-year career break
4:00 — Building a billion-dollar inside sales org
8:15 — The 4x4 method playbook
12:30 — Treating a job search like a sales pipeline
16:45 — The four stages of scaling revenue sequentially
20:00 — Navigating unrealistic founder and VC expectations
24:15 — Why founders must close their own early deals
28:30 — Auditing a broken revenue infrastructure
32:00 — Acquiring a team vs. hiring a team

Key takeaways

Treat your job search like a rigorous sales pipeline.
Never skip stabilization and foundation before trying to scale.
Technical founders must close their own early deals first.
Audit broken sales organizations before attempting to close business.
A playbook is useless without constant reinforcement and tracking.

Transcript

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 pursuitsalesolutions.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 season 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, Hello Sign, 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, creating new income streams.

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

Awesome. Thanks for joining the show and putting up with Adam. Although, although the introductions are always the best part of the show. Don't demean me, Dale.

Don't demean me. Oh. Inside joke, inside joke. Um so as a sale 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, 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 Hello sign 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 This is my jam, Dale. Um, I'll give you to kind of The first time he's 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. Um, I am from the San Francisco Bay Area and, um, I'm a little long in the tooth, um, particularly for tech.

Um, but I started out in the investment industry in the mutual fund space. I was at Franklin Funds, um, 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 that I could make a lot more money on the sales side. And so I transitioned to to sales, um, and I was 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. Um, 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. And so 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, this was zero to one, you know, it was ground up. Um, and I learned from the best in the world.

The the top investment sellers in the world. And, um, so literally, I 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. And so 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 site unseen in my late twenties calling on stockbrokers.

And I 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. And I went from being the only woman in the room in the investment industry to later being the oldest person in tech.

Um, but I learned a framework. I learned how to build playbooks. I learned how to build a business plan, right? And we know as sales leaders, that's really what it's all about, especially when you're starting ground up.

Um, and, you know, I was representing, I was a California girl representing a West Coast product in the mutual fund capital of the world. And, um, 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 the nature of the region. Um, 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. Yeah. So you, you know, this is the process, right? That you have to build, right?

Going from your, you know, more of your stabilization and into that foundational piece, right? And, um, you know, so 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? So it's like, you know, it was a very comprehensive playbook on how I was going to tackle the region and everything. But, um, 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, um, character and, um, you know, after a couple of years of building that northeast region, I moved down to New York and, um, left my career and decided I wanted to start a family. And I ended up becoming a 17-year stay-at-home mom. And, um, it 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.

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

Um, I walked away from my marriage candidly with nothing. No alimony, no child support, 100% care for my kids. And so my back was against the wall and I 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. Uh, but when I was but here's the key is, and this is kind of flash forward to what I'm doing now, I I asked myself, what did I do, you know, as an early thirty-year-old to be successful. And it went back to that business plan, that playbook.

And so I created a sales playbook 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 tried, I couldn't get any interviews, but have four conversations and whether it's a networking event or, you know, um, whatever it is, a day. And, um, and so, so, you know, then I went on to become a three-time sales leader, five-time uh, 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. Um, I, um, so, you know, I love, I I was not, I ran the sales org, um, I was the sales manager at Hello Sign 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.

So that that's a little bit about my background. I don't know if that even answered your question, Dale. Let let me ask. So we talk about the four stages, um, 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 to foundation, foundation to repeatability, or repeatability to scalability? And why? Um, I don't think that I mean, I think they're all hard. Um, I I think really where a lot of it comes down to um, 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?

Like, every Unrealistic 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 that I respect that you know, have far better education than I do. 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 until this conversation, I've never heard the four stages 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, um, you know, I I think a big part of being successful is having a leadership team or building out a, you know, a support system, whether it's your advisors or your VCs or your, um, CEO who's on board with making sure that each of the steps are handled before trying to move forward to the next stage. Well there there's some fluidity to those, right? You you get to like there's not like it's not like a single path either. Like we talk to a lot of companies, startups, founders, and and the reason why we started our own business was because we would get pitched, probably like you do, like we're investors.

Hey, we have a great funnel. Hey, there's tons of leads. Every customer's happy. Product's working.

And then like you get inside the business and you're like, okay, there's a lot of broken pieces to this 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 now you got to close business super quickly. So one of the things that we've been working with with a lot of our our founders and and revenue leaders is like, let's take one step back to create three steps forward. And it does it does allow them some breathing room.

Like if you're in there by yourself, you're the revenue leader, you got 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 coaching your reps? Like where 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'm doing, um, I stepped back after we sold sales compete about a year ago. And so I'm I'm doing a lot of, um, fractional sales leadership or fractional CRO work where I go in. The first thing I do is audit, you know, is really audit the organization to understand where the pieces are really broken, right?

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? But you've got to get the the infrastructure in place.

And I love what I'm doing now is I'm working with, um, founders who are going from founder led sales or maybe have a first or second, you know, sales person in their organization to creating a a an organization to scale. 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, um, you know, I think that's that's such a critical piece is making sure that that infrastructure is in place. And people are following.

Yeah. 100%. There's so many times, like you touched on a couple of things, right? VCs, I think certainly change the game, um, with their expectation.

And having the infrastructure in place and transitioning from founder-led sales, I find that often times, founders want to go right from founder-led sales to repeatability. Um, and then it's like, oh, let's just go hire a full-time sales leader and they're they're going to like 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 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. Sendoso's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process. Trust me, I led sales for a Sendoso competitor and I can tell you no one does gifting better than Sendoso. If you're looking for a proven way to win and retain more customers, visit sendoso.

com. I mean, I'm in an interesting part now where I've had 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 the this is a generalization, not all, but most of them come from either the technical or the product side.

I'm sorry, I haven't like having a little water. Um, the technical or the product side. And again, 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. I think that's fair. They don't, you know, they think they think, you know, in general, I mean, they 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 their sales leaders or hiring the wrong sales leaders. Maybe people are not experienced to do that, that's right. They 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 um 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 the I think this is part of being a mom, I'm good at wearing a lot of hats. You know, and I I can't even tell you how many people I've brought in or worked with in in sales organizations or revenue, you know, organizations that'll be like, oh my god, this is a shit show.

I'm like, I know, isn't that beautiful? Like this is the the stuff that we all have to figure out and and and get all those pieces in place. Yeah. Yeah.

I do think being a parent helps. Um I I I I will just leave that there. Um, but I I I do think being a parent helps. Um, 100%.

Yeah. You you you get to let them fail as well, right? I mean, we have we have these things where like we want to save everybody or like we think we're going to know best, but, you know, some of my best learners have come from reps that have had amazing success and show different ways of of calling or connecting or, um, that type of work. Elizabeth, as you as you moved, I'm curious as you transition from like a foundation process, so you you've built everything out, you got nice playbooks running.

Where what was the challenge on 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 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 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 I I feel like I could write a book on the difference between acquiring a team and hiring a team, right? And there's there's plusses and minuses on both, right? And in most cases when you've got a sales leader coming in, there's a there's a cross section, right? You've got some, you know, there's always 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. Yeah.

Right? It's just like it's got to be the reinforcement and making sure it's the measuring and tracking. Let's go do this. Right?

Yeah. So, you know, this is the process, right? That you have to build, right? Going from your, you know, more of your stabilization and into that foundational piece, right?

And, um, you know, so 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?

So it's like, you know, it was a very comprehensive playbook on how I was going to tackle the region and everything. But, um, 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, um, character and, um, you know, after a couple of years of building that northeast region, I moved down to New York and, um, left my career and decided I wanted to start a family.

And I ended up becoming a 17-year stay-at-home mom. And, um, it 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. In fact, my oldest is a an SDR now.

Um, so, you know, the apple doesn't fall too far from the tree. But, um, I, um, I did a ton of nonprofit work, a lot of fundraising, I raised over a million dollars for certain, um, nonprofits and event planning. Um, 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. Um, I walked away from my marriage candidly with nothing.

No alimony, no child support, 100% care for my kids. And so my back was against the wall and I 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. Uh, but when I was but here's the key is, and this is kind of flash forward to what I'm doing now, I I asked myself, what did I do, you know, as an early thirty-year-old to be successful. And it went back to that business plan, that playbook. And so I created a sales playbook 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 tried, I couldn't get any interviews, but have four conversations and whether it's a networking event or, you know, um, whatever it is, a day. And, um, and so, so, you know, then I went on to become a three-time sales leader, five-time uh, 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.

Um, I, um, so, you know, I love, I I was not, I ran the sales org, um, I was the sales manager at Hello Sign 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. So that that's a little bit about my background.

I don't know if that even answered your question, Dale. Let let me ask. So we talk about the four stages, um, 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 to foundation, foundation to repeatability, or repeatability to scalability?

And why? Um, I don't think that I mean, I think they're all hard. Um, I I think really where a lot of it comes down to um, 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? Like, every Unrealistic 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 that I respect that you know, have far better education than I do. 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 until this conversation, I've never heard the four stages 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, um, you know, I I think a big part of being successful is having a leadership team or building out a, you know, a support system, whether it's your advisors or your VCs or your, um, CEO who's on board with making sure that each of the steps are handled before trying to move forward to the next stage.

Well there there's some fluidity to those, right? You you get to like there's not like it's not like a single path either. Like we talk to a lot of companies, startups, founders, and and the reason why we started our own business was because we would get pitched, probably like you do, like we're investors. Hey, we have a great funnel.

Hey, there's tons of leads. Every customer's happy. Product's working. And then like you get inside the business and you're like, okay, there's a lot of broken pieces to this 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 now you got to close business super quickly. So one of the things that we've been working with with a lot of our our founders and and revenue leaders is like, let's take one step back to create three steps forward. And it does it does allow them some breathing room. Like if you're in there by yourself, you're the revenue leader, you got 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 coaching your reps?

Like where 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'm doing, um, I stepped back after we sold sales compete about a year ago. And so I'm I'm doing a lot of, um, fractional sales leadership or fractional CRO work where I go in. The first thing I do is audit, you know, is really audit the organization to understand where the pieces are really broken, right? 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? But you've got to get the the infrastructure in place. And I love what I'm doing now is I'm working with, um, founders who are going from founder led sales or maybe have a first or second, you know, sales person in their organization to creating a a an organization to scale.

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, um, you know, I think that's that's such a critical piece is making sure that that infrastructure is in place. And people are following. Yeah.

100%. There's so many times, like you touched on a couple of things, right? VCs, I think certainly change the game, um, with their expectation. And having the infrastructure in place and transitioning from founder-led sales, I find that often times, founders want to go right from founder-led sales to repeatability.

Um, and then it's like, oh, let's just go hire a full-time sales leader and they're they're going to like 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 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.

Sendoso's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process. Trust me, I led sales for a Sendoso competitor and I can tell you no one does gifting better than Sendoso. If you're looking for a proven way to win and retain more customers, visit sendoso.com.

I mean, I'm in an interesting part now where I've had 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 the this is a generalization, not all, but most of them come from either the technical or the product side. I'm sorry, I haven't like having a little water.

Um, the technical or the product side. And again, 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. I think that's fair. They don't, you know, they think they think, you know, in general, I mean, they 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 their sales leaders or hiring the wrong sales leaders.

Maybe people are not experienced to do that, that's right. They 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 um 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 the I think this is part of being a mom, I'm good at wearing a lot of hats. You know, and I I can't even tell you how many people I've brought in or worked with in in sales organizations or revenue, you know, organizations that'll be like, oh my god, this is a shit show. I'm like, I know, isn't that beautiful?

Like this is the the stuff that we all have to figure out and and and get all those pieces in place. Yeah. Yeah. I do think being a parent helps.

Um I I I I will just leave that there. Um, but I I I do think being a parent helps. Um, 100%. Yeah.

You you you get to let them fail as well, right? I mean, we have we have these things where like we want to save everybody or like we think we're going to know best, but, you know, some of my best learners have come from reps that have had amazing success and show different ways of of calling or connecting or, um, that type of work. Elizabeth, as you as you moved, I'm curious as you transition from like a foundation process, so you you've built everything out, you got nice playbooks running. Where what was the challenge on 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 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 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 I I feel like I could write a book on the difference between acquiring a team and hiring a team, right?

And there's there's plusses and minuses on both, right? And in most cases when you've got a sales leader coming in, there's a there's a cross section, right? You've got some, you know, there's always 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. Yeah. Right?

It's just like it's got to be the reinforcement and making sure it's the measuring and tracking. Let's go do this. Right? Yeah.

So, you know, this is the process, right? That you have to build, right? Going from your, you know, more of your stabilization and into that foundational piece, right? And, um, you know, so 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? So it's like, you know, it was a very comprehensive playbook on how I was going to tackle the region and everything.

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

And, um, it 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. In fact, my oldest is a an SDR now. Um, so, you know, the apple doesn't fall too far from the tree.

But, um, I, um, I did a ton of nonprofit work, a lot of fundraising, I raised over a million dollars for certain, um, nonprofits and event planning. Um, 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. Um, I walked away from my marriage candidly with nothing. No alimony, no child support, 100% care for my kids.

And so my back was against the wall and I 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.

Uh, but when I was but here's the key is, and this is kind of flash forward to what I'm doing now, I I asked myself, what did I do, you know, as an early thirty-year-old to be successful. And it went back to that business plan, that playbook. And so I created a sales playbook 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 tried, I couldn't get any interviews, but have four conversations and whether it's a networking event or, you know, um, whatever it is, a day. And, um, and so, so, you know, then I went on to become a three-time sales leader, five-time uh, 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. Um, I, um, so, you know, I love, I I was not, I ran the sales org, um, I was the sales manager at Hello Sign 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. So that that's a little bit about my background. I don't know if that even answered your question, Dale.

Let let me ask. So we talk about the four stages, um, 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 to foundation, foundation to repeatability, or repeatability to scalability? And why?

Um, I don't think that I mean, I think they're all hard. Um, I I think really where a lot of it comes down to um, 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? Like, every Unrealistic 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 that I respect that you know, have far better education than I do.

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 until this conversation, I've never heard the four stages 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, um, you know, I I think a big part of being successful is having a leadership team or building out a, you know, a support system, whether it's your advisors or your VCs or your, um, CEO who's on board with making sure that each of the steps are handled before trying to move forward to the next stage. Well there there's some fluidity to those, right?

You you get to like there's not like it's not like a single path either. Like we talk to a lot of companies, startups, founders, and and the reason why we started our own business was because we would get pitched, probably like you do, like we're investors. Hey, we have a great funnel. Hey, there's tons of leads.

Every customer's happy. Product's working. And then like you get inside the business and you're like, okay, there's a lot of broken pieces to this 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 now you got to close business super quickly.

So one of the things that we've been working with with a lot of our our founders and and revenue leaders is like, let's take one step back to create three steps forward. And it does it does allow them some breathing room. Like if you're in there by yourself, you're the revenue leader, you got 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 coaching your reps? Like where 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'm doing, um, I stepped back after we sold sales compete about a year ago.

And so I'm I'm doing a lot of, um, fractional sales leadership or fractional CRO work where I go in. The first thing I do is audit, you know, is really audit the organization to understand where the pieces are really broken, right? 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? But you've got to get the the infrastructure in place. And I love what I'm doing now is I'm working with, um, founders who are going from founder led sales or maybe have a first or second, you know, sales person in their organization to creating a a an organization to scale. 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, um, you know, I think that's that's such a critical piece is making sure that that infrastructure is in place. And people are following. Yeah. 100%.

There's so many times, like you touched on a couple of things, right? VCs, I think certainly change the game, um, with their expectation. And having the infrastructure in place and transitioning from founder-led sales, I find that often times, founders want to go right from founder-led sales to repeatability. Um, and then it's like, oh, let's just go hire a full-time sales leader and they're they're going to like 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 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. Sendoso's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process.

Trust me, I led sales for a Sendoso competitor and I can tell you no one does gifting better than Sendoso. If you're looking for a proven way to win and retain more customers, visit sendoso.com. I mean, I'm in an interesting part now where I've had 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 the this is a generalization, not all, but most of them come from either the technical or the product side. I'm sorry, I haven't like having a little water. Um, the technical or the product side.

And again, 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.

I think that's fair. They don't, you know, they think they think, you know, in general, I mean, they 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 their sales leaders or hiring the wrong sales leaders. Maybe people are not experienced to do that, that's right.

They 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 um 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 the I think this is part of being a mom, I'm good at wearing a lot of hats. You know, and I I can't even tell you how many people I've brought in or worked with in in sales organizations or revenue, you know, organizations that'll be like, oh my god, this is a shit show. I'm like, I know, isn't that beautiful? Like this is the the stuff that we all have to figure out and and and get all those pieces in place.

Yeah. Yeah. I do think being a parent helps. Um I I I I will just leave that there.

Um, but I I I do think being a parent helps. Um, 100%. Yeah. You you you get to let them fail as well, right?

I mean, we have we have these things where like we want to save everybody or like we think we're going to know best, but, you know, some of my best learners have come from reps that have had amazing success and show different ways of of calling or connecting or, um, that type of work. Elizabeth, as you as you moved, I'm curious as you transition from like a foundation process, so you you've built everything out, you got nice playbooks running. Where what was the challenge on 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 where's the challenge once you kind to get all that foundational stuff laid and you're trying to scale the business? Where do you find the 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 I I feel like I could write a book on the difference between acquiring a team and hiring a team, right? And there's there's plusses and minuses on both, right?

And in most cases when you've got a sales leader coming in, there's a there's a cross section, right? You've got some, you know, there's always 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. Yeah. Right? It's just like it's got to be the reinforcement and making sure it's the measuring and tracking.

Let's go do this. Right? Yeah. So, you know, this is the process, right?

That you have to build, right? Going from your, you know, more of your stabilization and into that foundational piece, right? And, um, you know, so 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? So it's like, you know, it was a very comprehensive playbook on how I was going to tackle the region and everything. But, um, 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, um, character and, um, you know, after a couple of years of building that northeast region, I moved down to New York and, um, left my career and decided I wanted to start a family. And I ended up becoming a 17-year stay-at-home mom. And, um, it 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. In fact, my oldest is a an SDR now. Um, so, you know, the apple doesn't fall too far from the tree. But, um, I, um, I did a ton of nonprofit work, a lot of fundraising, I raised over a million dollars for certain, um, nonprofits and event planning.

Um, 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. Um, I walked away from my marriage candidly with nothing. No alimony, no child support, 100% care for my kids. And so my back was against the wall and I 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. Uh, but when I was but here's the key is, and this is kind of flash forward to what I'm doing now, I I asked myself, what did I do, you know, as an early thirty-year-old to be successful.

And it went back to that business plan, that playbook. And so I created a sales playbook 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 tried, I couldn't get any interviews, but have four conversations and whether it's a networking event or, you know, um, whatever it is, a day.

And, um, and so, so, you know, then I went on to become a three-time sales leader, five-time uh, 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. Um, I, um, so, you know, I love, I I was not, I ran the sales org, um, I was the sales manager at Hello Sign 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. So that that's a little bit about my background. I don't know if that even answered your question, Dale. Let let me ask.

So we talk about the four stages, um, 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 to foundation, foundation to repeatability, or repeatability to scalability? And why? Um, I don't think that I mean, I think they're all hard.

Um, I I think really where a lot of it comes down to um, 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? Like, every Unrealistic 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 that I respect that you know, have far better education than I do. 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 until this conversation, I've never heard the four stages 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, um, you know, I I think a big part of being successful is having a leadership team or building out a, you know, a support system, whether it's your advisors or your VCs or your, um, CEO who's on board with making sure that each of the steps are handled before trying to move forward to the next stage. Well there there's some fluidity to those, right? You you get to like there's not like it's not like a single path either.

Like we talk to a lot of companies, startups, founders, and and the reason why we started our own business was because we would get pitched, probably like you do, like we're investors. Hey, we have a great funnel. Hey, there's tons of leads. Every customer's happy.

Product's working. And then like you get inside the business and you're like, okay, there's a lot of broken pieces to this 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 now you got to close business super quickly. So one of the things that we've been working with with a lot of our our founders and and revenue leaders is like, let's take one step back to create three steps forward.

And it does it does allow them some breathing room. Like if you're in there by yourself, you're the revenue leader, you got 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 coaching your reps? Like where 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'm doing, um, I stepped back after we sold sales compete about a year ago. And so I'm I'm doing a lot of, um, fractional sales leadership or fractional CRO work where I go in.

The first thing I do is audit, you know, is really audit the organization to understand where the pieces are really broken, right? 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?

But you've got to get the the infrastructure in place. And I love what I'm doing now is I'm working with, um, founders who are going from founder led sales or maybe have a first or second, you know, sales person in their organization to creating a a an organization to scale. 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, um, you know, I think that's that's such a critical piece is making sure that that infrastructure is in place.

And people are following. Yeah. 100%. There's so many times, like you touched on a couple of things, right?

VCs, I think certainly change the game, um, with their expectation. And having the infrastructure in place and transitioning from founder-led sales, I find that often times, founders want to go right from founder-led sales to repeatability. Um, and then it's like, oh, let's just go hire a full-time sales leader and they're they're going to like 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 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. Sendoso's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process. Trust me, I led sales for a Sendoso competitor and I can tell you no one does gifting better than Sendoso.

If you're looking for a proven way to win and retain more customers, visit sendoso.com. I mean, I'm in an interesting part now where I've had 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 the this is a generalization, not all, but most of them come from either the technical or the product side. I'm sorry, I haven't like having a little water. Um, the technical or the product side. And again, 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. I think that's fair.

They don't, you know, they think they think, you know, in general, I mean, they 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 their sales leaders or hiring the wrong sales leaders. Maybe people are not experienced to do that, that's right. They 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 um 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 the I think this is part of being a mom, I'm good at wearing a lot of hats.

You know, and I I can't even tell you how many people I've brought in or worked with in in sales organizations or revenue, you know, organizations that'll be like, oh my god, this is a shit show. I'm like, I know, isn't that beautiful? Like this is the the stuff that we all have to figure out and and and get all those pieces in place. Yeah.

Yeah. I do think being a parent helps. Um I I I I will just leave that there. Um, but I I I do think being a parent helps.

Um, 100%. Yeah. You you you get to let them fail as well, right? I mean, we have we have these things where like we want to save everybody or like we think we're going to know best, but, you know, some of my best learners have come from reps that have had amazing success and show different ways of of calling or connecting or, um, that type of work.

Elizabeth, as you as you moved, I'm curious as you transition from like a foundation process, so you you've built everything out, you got nice playbooks running. Where what was the challenge on 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 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 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 I I feel like I could write a book on the difference between acquiring a team and hiring a team, right? And there's there's plusses and minuses on both, right? And in most cases when you've got a sales leader coming in, there's a there's a cross section, right?

You've got some, you know, there's always 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.

Yeah. Right? It's just like it's got to be the reinforcement and making sure it's the measuring and tracking. Let's go do this.

Right? Yeah. So, you know, this is the process, right? That you have to build, right?