Chapter 1: What inspired Elizabeth Andrew's career transition from stay-at-home mom to tech leader?
I've worked for tech companies many times. 90% of startups fail. And I've worked for brilliant CEOs that come from the technical and product side. They all think the product's going to solve itself. It never does, right? And, you know, I've been in a situation where I've been hired and there's $4 million in revenue and they want me to bring in $20 million next year. That's not a realistic goal.
The difference between companies that are successful and don't and are not successful is because they have a strategy.
Elizabeth Andrew is a top producing technology CEO and founder, five-time sales leader and creator of the 4x4 method, Silicon Valley's secret to exponential growth. Her work has rewritten the growth playbook behind some of the most dramatic success stories in tech, revealing how bold vision, disciplined execution and audacious goals turn disruption into lasting impact.
I would love to talk about the stages of founder selling. Most people listening are entrepreneurs, solopreneurs or small teams. They're probably selling themselves. Do you find it changes much once you get to a team of 50 to 100?
You need to be able to hand off the process, but you also don't want to create too much process too soon to slow down the business, right? So it's like, how do you build that out?
It spans the globe like a super high school internet. Today, Apple is going to reinvent the phone. It's not over until I win. The Living Your Legacy podcast. For those who live to leave a legacy. That's extraordinary. The impossible. Oh, that is sensational.
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Chicago was the lead. Usain Bolt is the fastest man on the planet. You can live your dream. Hello and welcome back to another episode of Legacy Makers. Joining me today is Lizzie. We've known each other for a while. We actually met on Richard Branson's island and she's got a fascinating backstory.
Went from being a stay-at-home mom for 17 years to a tech CEO working with some of the biggest brands in the world, having multiple exits, leading massive sales organizations. So pretty much a full 360 pivot and that's what we're going to talk about today. Welcome to the show.
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Chapter 2: What is the significance of the 4x4 method in personal and professional growth?
What makes my story interesting is that I relaunched a career after 17 years as a stay-at-home mom at nearly 50 years old with no tech experience in San Francisco and the Silicon Valley and went on to accomplish all of it.
Yeah, very competitive area, right?
Very competitive area.
Probably not favorable to someone that's been a stay-at-home mom for 17 years either, right?
No, not at all.
A lot of battles there.
Not at all. And I know I've shared with you, but I started out my career early on in Wall Street. But Wall Street was very much demonized. I hadn't worked in 17 years. I was completely unemployable. Nobody would talk to me. And, you know, I joke a lot with my friends. I went from being the only woman in the investment industry to the oldest person in tech.
Wow.
So let's talk about that. One day you wake up and you go, I'm going back to corporate, right? I imagine. Tell me about that moment.
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Chapter 3: How does realistic goal setting impact business success?
So I learned how to build from the ground up. And then they transferred me, after several years of doing that, they transferred me to the East Coast to open up the New England region, thinking we were a West Coast bank. And so I built a business plan and I took that region from zero to 70 million. So I learned how to build playbooks. I learned how to build from the ground up early on.
So when I was totally unemployed and I've got these three beautiful kids and I'm worried about becoming homeless, I said, what did I do in my 20s and 30s that made me successful? And it was having that strategy, that playbook. So I built a sales playbook, for lack of a better term, or a business plan for my job search.
And, you know, it's as simple as like, you know, I mean, you're an elite athlete now. You know, you can't like you can't say I'm going to lose 20 pounds in two weeks and have it happen. You have to have a plan. Yeah. You know, four meetings a day, four days a week, Monday through Friday, you know, always make sure you're scheduled two weeks out. And I created that plan for my for my job search.
And so over time.
Do you know how many interviews till you landed the good gig?
Well, it was a lot. My first, I found my first job actually in the mutual fund industry. And that's the job I found on Craigslist. And that was 20 hours a week working for the West region director of sales. And I did that for about a year and felt like there's no fun to be had in financial services. And it was interesting too, because I was an investment wholesaler and
You know, there were a lot of gender issues. I had a lot of friends of mine say, why don't you just become an assistant? And there is nothing. I mean, it's a very hard job. It's just not my skill set, you know, and they would never have said that to my ex-husband. Right. You know, but it wasn't until I actually kind of got a sales assistant role that I was able to really start rebuilding.
Yeah. So let's ask, you know, that's I'm sure there's a whole more to that story. But let's fast forward. What are you doing now?
Yeah, so in 2023, I was VP of sales of an AI company and I found myself working 80 hours a week and had three days off in a year. It almost killed me with a celebrity VC. And, you know, I finally, after a year of this, I looked myself in the mirror and I said, what am I doing? I'm killing myself. And so I left. I became a founder of a tech startup, which we sold after a year and a half.
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Chapter 4: What are the essential components of a strategic plan in tech startups?
I get a lot of high achievers, some founders. that, you know, we're just in that time where millions of people are feeling stuck or stagnant. People are tired of working for the man. They want multiple sources of income. They want to take on passion projects.
I've noticed that since COVID, right? Like, I mean, that was the big, like... you know, straw that broke the camel's back, maybe like they realized, you know.
Right. People want, and especially, you know, one of the things I talk about, I do corporate too. I do workshops because we're living also in a time where engagement, employee engagement is at an all-time low. 87% of employees globally are not engaged in the workforce, right? And some of it applies to that.
And I read a stat too, I think the average nine to five works four hours a day. Like they do four hours of whatever and four hours of actual work. So that probably goes hand in hand with that.
Yeah, and especially for kids, you know, it's interesting because when I got into tech, my first sales role, I was selling APIs to engineers. I didn't know what an API was when I got the job. And everybody that I worked with was between 25 and 35. You know, it was typical SAS sales, software sales students.
And, you know, but it was really interesting because I was working cross generationally and we're at a time. And this is something that I talk to corporations about, too. We're in a time, the first time in the history of the world where we have five generations working together.
Oh, wow.
Okay.
And how do you navigate that?
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Chapter 5: How can cross-generational teams enhance organizational performance?
So it's having that plan. And I've worked for brilliant CEOs that come from the technical and product side. They all think the product's going to solve itself. It never does. Right. And, you know, I've been in a situation where I've been hired and there's four million in revenue and they want me to bring in 20 million next year. That's not a realistic goal.
So it starts with setting realistic and attainable goals. And that, you know, when I work with these workshops, it depends a lot. I do a lot of one on one coaching in this because for some people, they don't even know where to start. Other people do have goals that they know what they want to achieve. So that's the big number one part of the foundation.
The next is productivity, which has really become so important. And I know I've been in some of your masterminds and workshops and heard your calls. One of the things that you taught me that I love is the, I think you called it the top five priorities. You write them down at the end of the day and you wake up and knock them out. Even knowing how to create a plan post-pandemic, it's really easy.
Yeah. On Instagram. Yeah. I mean, I always say most people, successful people run their day. It's a great saying I heard one day and unsuccessful people have their day run for them.
Yep.
So I mean, that's, you know, a lot of people work a lot now, but they're not very productive, you know, all the time.
Yeah. So that's a big part of the second level of the pillar. The third is the strategic plan. And that is, I have a lot of very detailed programs around that one is creating, you know, dashboards around KPIs and and tracking them and how you manage your KPIs in order to attain your goal, right? It's like training for your marathon or your triathlon or whatever it is, right?
And then the last one is the execution.
Okay. Talk about that because I think a lot of people fall on that too because they have all these ideas but then they don't put it into practice.
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Chapter 6: What challenges do founders face when scaling sales teams?
Yeah.
Yeah. I mean, nobody's going to steal your idea. Yeah. But, yeah, I mean, it all falls into the execution. And, you know, the best parallel to that is a training regimen. You know, it's the small, consistent.
So let's talk about the sales side now for a few minutes, too. I think you've got a lot of experience there. So I would love to talk about the stages of founder selling. Most people listening are entrepreneurs or small teams. They're probably selling themselves. And then maybe hiring the first sales rep. building the team to 10, 50 and beyond.
And I'm interested, do you find it changes much once you get to a team of 50 to 100? Yeah, absolutely. So just those stages and how they change.
Absolutely. And that's a critical, there's the, you know, you've probably read Peter Thiel's book, Zero to One. Mm-hmm. That's a very different stage than going from one to 10 and then taking it beyond there. I've led teams in every stage of that, but I actually love, I went through an acquisition with Dropbox. I led the sales org for HelloSign for a year, reporting to our COO.
But ultimately, you know, we're a big publicly traded company and I like being able to be in those earlier stages when you can work cross-functionally and solve problems, right? So those are very critical stages because you need process and you need to be able to hand off the process, but you also don't want to create too much process too soon to slow down the business, right?
So it's like, how do you build that out? And again, it comes down to creating that business plan, the sales playbook, the strategy. And you can apply that. This is the thing. And this is what I'm doing with the four by four method that I'm so passionate about. Right. You can apply that to your own life. And I talk about this to my in all of my groups. Like I'm the CEO of Lizzie.com. Sure. Right.
Like bring in more than you spend. You know, you just kind of you want to manage yourself. I have one of the big, big things that really helped me early on in my rebuilding of my career was creating my personal board of directors. Uh-huh. You know, and some of the people are friends that I met on Necker Island. Some know they're on my board of personal board of directors.
Some don't, you know, but they'll be like, Hey, Rudy, I'm just, and I think I texted you the other day, you know, Hey, can I run something by you? Right. Like create those people in your life that you can go to that can give you direction. Right.
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Chapter 7: How does Elizabeth Andrew define effective execution in business?
Yeah, I mean, that's one of the things that I work with a lot with founders who are going, they have to be founders, for me to work with them, and it's mostly tech companies, tech founders, software specifically, but I have done other tech companies. They have to have sold some deals on their own or I won't work with them.
So they typically don't have the funding to hire on a VP of sales at that stage. So that's a perfect time to bring on a fractional VP of sales or a fractional CRO where I can help with the hiring, but you can also hire somebody that is junior and hungry and they're getting the coaching and the structure. Yeah. in place.
So they're not just winging it from a product led, you know, you just bring on, you're not just bringing on a first sales hire who doesn't know what they're doing.
Yeah. Yeah. I think that first one's hard because a lot of the entrepreneurs I work with, they, they can sell it themselves because they're so passionate about it. They created it. They're the face of the brand often, but then they bring in a rep and, you know, they have to develop a Right. Yeah. Right.
detailed you can get and how much it improves the onboarding process when you have those training. Right. So how do you, you know, in these big corporations, is it like that where they have this like two week training system? Yeah, absolutely.
It depends. So early on, not so much.
Sure.
Right. And there's a lot of A-B testing.
Yeah.
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Chapter 8: What resources are available for those looking to reinvent their careers?
which was brilliant for tech, but they broke it into, you know, your sales development reps who do just cold calling. And then you've got the, you know, there's all these different stages of the funnel. So it's more like a conveyor belt.
That's how we do ours. Yeah.
Yeah. But it changes the dynamic a little bit. Yeah. And that was great when everything was thriving.
Yeah. So last couple of questions. I would love for you now just to talk about your episode, what some things people will get out of the rest of your story and the episode.
Yeah, I'm really looking forward to sharing some stories more in depth about, you know, that relaunch journey. And I've reinvented myself multiple times. I mean, you know, from, you know, breaking into Wall Street and that male-dominated industry in the Northeast in particular to becoming a stay-at-home mom. I'll talk a little bit about, I did a ton of nonprofit work.
I'm not one of those people that can just play tennis all day. And yeah, so I did a ton of nonprofit work in the 17 years for, different organizations. And ironically, that stuff is harder than anything I've done professionally because you're dealing with volunteers. You can't hire them. Right. And yet, you know, it wasn't until I took all of that off my resume, anybody would even talk to me.
Well, it's probably also harder because if you go from Wall Street, like high-performing, A-type, like hungry people, and then obviously a lot of nonprofits, like they're doing it on the side of volunteers. Right. You can't get them to go maybe quite as quick as Wall Street, I imagine.
Yeah, although where I was doing that, that is one thing. It was a suburb of New York.
Okay.
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