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 sell 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 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? The Living Your Legacy podcast. For those who live to leave a legacy. That's extraordinary. The impossible. Oh, that is sensational. Jordan. Open. Chicago was the lead. You said Paul 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. Thank you so much, Rudy. It's so great to be here and to see you again, as always. So I'm excited for this because, you know, I love how you kind of reinvented yourself, right? And you did it in a big way, too. It wasn't like you were a stay-at-home mom, then you started an Etsy store, right? You went back into, you know, big, ugly corporate America, led some massive teams, you know, big teams, big exits, and obviously became successful. And now you've done a lot of public speaking, TED Talks, stuff like that. So do you mind just telling everyone the minute summary of this journey? Yeah, absolutely. That summarizes it very well. I'm a former tech startup CEO, five-time sales leader, three-time VP of sales. I've had three exits, led teams at some huge companies, HelloSign, Dropbox, Pluma, Skillsoft, a number of great, well-known companies. But that's not what makes my story interesting. 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. And 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 I joke a lot with my friends. I went from being the only woman in the investment industry to the oldest person in tech. 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. Well, it was a little bit less glamorous than that. You know, like a lot of people, I hit rock bottom. I got out of a 21 year marriage, walked away with three beautiful kids, hadn't worked in 17 years, and I had 100 percent responsibility for supporting them. And I found I literally found myself completely unemployable. In fact, at one point I applied for a job cleaning houses. Apparently you have to be a Latin American woman to get a job cleaning houses. And, but I was in San Francisco and I had a really good dynamic early career and I knew how to reinvent myself. So I did, I was able to build a plan for myself. I literally created a strategy, a playbook or a business plan for my, my job search. So, so, cause I imagine that story is a bit like maybe like, you know, Walt Disney, where the, And the Mickey Mouse concept gets rejected many times before it's accepted. I imagine it wasn't your first interview where they were like, heck yeah, let's do it, right? So tell us that. Yeah. I mean, this was in... Okay, so I moved back to the Bay Area from the East Coast. I raised my kids in Connecticut. And I moved back to the Bay Area in 2011. Okay. So the 2010s, I mean, it was on fire, but it certainly was not open to older people, people returning to the workforce, people with a career gap, certainly not people with a Wall Street background. And I actually found my very first job on Craigslist. Wow okay And then what happened from there How did you work up Well so what happened is nobody would talk I couldn get recruiters to talk to me or anything And you know to really dig into this and I just give you a 30 overview but when I started out in my 20s and early 30s in the investment industry it was the mutual fund business. And I was a mutual fund wholesaler, and I was on a founding team that took Wells Fargo Asset Management's first mutual fund company from zero to over a billion dollars in assets. So I learned how to build from the ground up. Yeah. 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, you know, 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, 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, um, 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. Um, 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 and 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. And now I'm really trying to help other people create a playbook to reinvent themselves and to build their own plan. And is this people reinventing themselves that are stay at home mom trying to go out and get a job again? Are these entrepreneurs trying to grow a team and a sales team? Are these corporations trying to grow their big corporate sales teams? Who? Well, it's really interesting. First of all, the program that I've built, it's called the four by four method, Silicon Valley's secret to exponential growth for your personal and professional development. It can really apply to any circumstance. It applied to a job search for me, right? So I'm doing masterminds and workshops for individuals. 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, right? Like they do four hours or 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 SaaS sales students, 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, So we're in a time, the first time in the history of the world where we have five generations working together. Oh, wow. And how do you navigate? Yeah, yeah. I mean, it's so different, too, because, yeah, those five generations, the technology gap is like massive. Right. Whereas if you go back 50 years, it wasn't that different. Right. Right. And I mean, I'm Gen X, but I have older brothers that are eight and ten years older. They're baby boomers. You know, I have three kids. And, you know, so it's you can get you can build really high performing teams if you're open to that, you know, and on both ends of the age spectrum, you get people that are saying, oh, those darn millennials or, you know, and that doesn't create a good workforce. Right. So I do a lot of speaking around that as well. So let's just talk about what you're doing now and how that applies to people listening. If someone's listening and they are in that pivot phase, how do they start that journey? Yeah Well right now I actually going to be launching a mastermind next month in May which is going to be a six month mastermind which will have one on one coaching But I have it called the four by four method And there really a four piece four pillars to this You know it it setting realistic and attainable goals That one That the first one And that a big piece of it And I've worked for tech companies many times. 90% of startups fail. The difference between companies that are successful and don't and are not successful is because they have a strategy. I've looked for multiple Y Combinator companies that tend to be more successful. 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 sell 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. 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 and 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 where you one of the things that you taught me that I love is the I think you called it the top five priorities. Yeah. You write them down at the end of the day and you wake up and knock them out. You know, even even knowing how to create a plan post pandemic, it's really easy. Yeah. Thought on Instagram. Yeah. 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 ran 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, I see it 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, um, and tracking them and how you manage your KPIs and, you know, in, in order to, to attain your goal. Right. It's like training for your, your marathon or your triathlon or whatever it is. Right. Um, and then the last one is the execution. Okay. Uh, you talk about that because I mean a lot of people fall on that too, because they have all these ideas, but then they don't put it into practice. Well, it's interesting because I do get, one of the things I also do a little bit on, on the side is consulting early stage founders on how to build a sales organization to go from founder led sales to building the infrastructure to scale. Right. And so, you know, of course, the very first thing that every I won't work with any founders that haven't at least closed their own deals. Yeah. Right. And the thing that most people do is they want you to send and sign an NDA. And I'm always happy to sign the NDA. I have no problem signing an NDA. But it's, you know, part of me inside is like, it's not the idea. It's the execution. Yeah. Yeah. I mean, NDA is I mean, yeah, they're interesting. I've been asked a lot, too, and I'm like, unless you've cured cancer or figured out this new fuel source, it's like, yeah. Yeah, I mean, nobody's going to steal your idea. 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. You've got a lot of experience there. So I would love to talk about the stages of founder selling. Most people listening are solopreneurs or small teams. They're probably selling themselves. Yeah. 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. Absolutely. And that's a critical, there's the, you know, you've probably read Peter Thiel's book, Zero to One, right? That's a very different stage than going from one to ten and then taking it beyond there. And I, you know, it's like I've done, I've led teams in every stage of that. But I actually love, like, I went through an acquisition with Dropbox. We were there for, I led the sales org for HelloSign for a year reporting to our COO. So 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 it's it's a 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 dot com. 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, 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. And let's talk, you know, on the sales side, someone's selling themselves right now. How do they find, because I think that's like, it's almost like the first million is the hardest, the first sales reps, the scariest, because, you know, they never close like you close, right? You're always a founder, generally you're always going to close your own deals better than an average rep you find the first time But how do you find like how do you go about bringing in that first person Yeah I mean that one of the things that i work with a lot with founders who are going they have to be founder for me to work with them and it mostly tech companies tech tech founder software specifically but i have done other tech tech companies um they have to have sold some deals on their own or i won't work with them um they also um you know they so they typically don't have the funding to hire on a VP of sales at that stage. Right. So that's a perfect time to bring on a fractional VP of sales or a fractional CRO where, you know, 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 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 The 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 script of some sort and training. And, you know, we have we have about 50 sales reps in one of my businesses and we have like it's about 30 hours of onboarding and 55 action items they go through to be onboarded properly. But we didn't used to have any of that. And it's, you know, it's interesting how 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, though. Early on, not so much. Sure. Right. And there's a lot of A-B testing. Yeah. And, you know, one of the things as a VP of sales, when I'm hiring in early stage companies, I really look at, you know, you really have to look at the salespeople and where they're coming from. You know, I can't even tell you how many times I've had somebody that's come from a Google or a Salesforce or something and they cannot handle it in an early stage because they're like, where are my leads? Well, you've got to go get them. Where's my pitch deck? Even the personality like we pretty much when we hire, we know we actually internally grade someone and then watch it 30 days after calls if I grade matches. And we're pretty accurate now, like just from their confidence level and charisma. Right. 90 percent of the time, they're going to be good if they've got that. If they're a bit monotone or not that confident, a bit average. Right. They don't ever end up doing that well. It's rare that they become like a top closer. Right. So I think part of it's the personality, too, especially with sales. Yeah. And where you fit, you know, and it's interesting in tech sales, too, is, you know, it's very different in many ways than Wall Street sales because back in the day. Yeah, it's more technical, analytical people, right? So it's probably less about the confident, rah-rah sales rep, more analytical rep. Yes, but it's also back in the day, it was back when carrying a bag was carrying a bag. And I actually preferred that model better as a sales leader because, again, it's like you're the CEO of your own territory. So you source your own leads, you close your own, you know. And it was actually the early 2000s. It was an early senior leader at Salesforce, which was brilliant for tech. But they broke it into, you know, your sales development reps who do just cold calling. And 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. 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 in 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 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 perform, a type, like hungry people, and then obviously not a lot of nonprofits, like they're doing it on the side or volunteers. Like you can't get them to go maybe quite as right. Wall Street, I imagine. Yeah. Although we you know where I was doing that, that is one thing where it was a suburb of New York. OK. So a lot of the people were coming out of careers. Got it. Okay. So last question. Someone wants to learn more about you, this four by four method, maybe attend the upcoming masterminds, see some of your talks. Where do they find you? Yeah, absolutely. First of all, Elizabeth Andrew dot com. There's no S on Andrew. So www.elizabethandrew.com. I can be reached at Elizabeth at Elizabeth Andrew dot com. I'm on LinkedIn at Elizabeth A. Andrew. I'm on Instagram at the Elizabeth Andrew. And I would love to have participants in my mastermind next month. Good. Love it. Yeah. Well, excited for your episode to come out. Guys, go check that out. And hopefully you learn a little today about, you know, this four by four method pivoting and of course sales, which was a big part of the discussion and the background here. And of course, you know, learn more in the full episode. So as always, keep working hard, have an impact and build a legacy. I'll see you guys soon. Take care. you
