Entrepreneur Intel

Joining the show this week is a 5x sales leader who helps SaaS startups find opportunities to break new ground and make things grow. Please welcome to the show, CEO and Founder at Elizabeth Andrew consulting, Elizabeth Andrew!

Elizabeth sits down with Host Wes Mathews to dive into some of the biggest challenges startup founders face. Elizabeth shares the challenges of founder led sales, the obstacles to overcome when returning to the workforce and the importance of learning on the job. 
 
Takeaways: 
  • One of the most important lessons in entrepreneurship is that anything is possible, even amidst challenging times. Never give up, as success is achievable by anyone willing to persevere.
  • The most significant obstacle for people returning from a career break is the perception that they are out of touch with current tools and trends. To combat this, immerse yourself in industry events and actively seek out learning opportunities
  • Startup success heavily depends on effective sales; relying solely on the product's intrinsic value is a common mistake. Early sales hires should be strategic, avoiding premature VP appointments or inexperienced salespeople to ensure sustainable growth.
  • Consider being conservative with funding even when it is available, to avoid running out of funds. Be sure to cherish small milestones in your startup journey, as these moments signify growth and progress.
  • If you're entering the job market without prior experience, especially post-2020, you need a strong work ethic and motivation to succeed. Ensuring team engagement in a remote or hybrid work environment is crucial.
  • It is important to conduct an audit to identify and address weaknesses within a company. Establishing a clear ideal customer profile and implementing effective sales processes can significantly improve outreach and sales functions.


Quote of the Show:
  • “I like wearing a lot of hats. I'm good in the startup space. I like building, I like growing, I like solving problems.” - Elizabeth Andrew



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Creators & Guests

Host
Wes Mathews
Producer
Liam Gousios

What is Entrepreneur Intel?

Welcome to Entrepreneur Intel, a podcast where we discuss the most important strategies for success from amazing entrepreneurs. Host Wes Mathews sits down with business owners to learn about how they got started running their own business, what helped them succeed and the biggest lessons they learned along the way.

Be sure to catch new episodes every Thursday morning, and to make sure you never miss out on any insights, don’t forget to subscribe to Apple Podcasts, Spotify, You Tube or wherever you get your podcasts.

This show is sponsored by Stealth Consulting, your Fractional CMO. Stealth provides the roadmap and accountability to reach your business and marketing goals. Learn more at https://stealthconsulting.com/

Wes: I am super excited, uh, today. I want to introduce, uh, the guest we have today. Uh, she was a stay at home mom for 17 years who joined into tech in her late forties with zero experience in Silicon Valley. Uh, she's helped SaaS startups find opportunities to break new ground and make things grow. Five times sales leader has been part of three successful exit.

I think one of those you just did like rather recently. Um, she's led sales functions at HelloSign, Dropbox, and Skillsoft. The CEO and founder at Elizabeth Andrew Consulting and, uh, Elizabeth Andrew, welcome.

Elizabeth: Thank you so much, Wesley. It's great to be here and, uh, super excited for the conversation

Wes: Well, I'm super excited to meet you. And one thing is I think this is the first podcast I, I shaved my beard. I may, when I first talked to you, I had a big. I end up shaving it, but, um, you know, I got to ask you a question. I ask everybody the question that comes on the podcast, cause I think it's a really important one.

You have a really great wealth of experience, like from being a mom, from Silicon Valley tech startup, launching your own company, selling that to where you're at today. Um, you know, what's, what's one of the most important lessons you've learned thus far, uh, being an entrepreneur.

Elizabeth: I would say the most important lesson is anything is possible. Literally anything is possible. And this is such a time in the world where I think a lot of people are going through a lot of things. And, um, you know, I certainly have a lot of incredible colleagues who've lost jobs or whatnot over the last year in tech.

And, you know, just don't give up because, um, if I can do it, anybody can do it.

Wes: So I w I want to start back. The first bullet point is, is, is really, it's a lot. It's a stay at home mom for 17 years, uh, joined a tech company in her late forties with no experience in Silicon Valley. So, so talk about that, you know, being a mom, like what led you to get back out there and then join tech in Silicon Valley, that's, it's a big jump.

Elizabeth: Yeah. Um, well, thank you. I, uh, I have a, I have a very unusual background for tech. I'm from the San Francisco Bay Area. I actually started out in the investment industry in my twenties and thirties in the mutual fund space. Um, and I was at Franklin Funds and then Wells Fargo Asset Management. Um, I helped Wells Fargo build their very first mutual fund company because the, um, the Glass Steagall Lithium.

So banks were able to sell investment products. And we took that, a team of four of us, the founding team of four of us, took it from zero to over a billion dollars in assets, um, for Wells Fargo. And, um, the last region we went into as an investment, uh, firm was the Northeast, because that's kind of the mutual fund and investment capital of the world.

And so they asked me to go open up that region, um, and I did, I moved out, um, I think it was Gosh, I was in my late twenties and, uh, I moved out. My family said, go for two years, have a great time. Don't fall in love. And, um, you know, I, I moved to Boston and I know you're in Michigan. Um, you know, as a California girl in January had never lived in the Northeast or anywhere where it snowed that much.

And, uh, I was calling on stockbrokers and this is back when carrying a bag was carrying a bag. And, um, you know, it was, it was fun. I took that region from zero to 70 million in sales. Um, After a couple of years of mutual fund wholesaling out there, I didn't listen to my parents as most young kids do and, uh, uh, ended up getting married to a New Yorker and moved down to New York and spent 17 years as a stay at home mom in the Connecticut area.

And, uh, um, it was, it was great. You know, I, um, had a really interesting time. I did a ton of nonprofit. during that time. I spent 17 years working on nonprofit organizations, and, um, you know, it was an interesting place to do that, too, because they were mostly women that were stay at home moms that were contributing to nonprofits, and most had come out of big careers.

A lot of the things I did in those years were harder than anything I've done professionally. Um, you know, but it's not until you take all of that off your list. that anybody will pay any attention to you because they don't take it seriously. Right. So, um, but you know, you're dealing with volunteers, you can't fire them if they don't do their job.

And, um, you know, it can be challenging doing nonprofit work. Um, but in 2011, um, we decided to move back to California and, um, move to San Francisco. My kids were getting a little older. My oldest was starting in high school. And so, um, you know, I felt like it was time to get back to work. And I, um, It was completely unemployable.

Nobody would hire me. You know, I'd spent 20 years on the East Coast, 17 out of the workforce, in a totally different part of the world. And, um, you know, I'd lost a lot of my connections. My childhood connections were, of course, still there, but, you know, most of them were in the suburbs and married and, you know, And, um, so I had to start from the ground up and I found my very first job on Craigslist, uh, working for Putnam Investments for the West Region Director of Sales.

Um, you know, and it was kind of a sales enablement role, a lot of admin kind of stuff, which is not my strength, but, uh, got me back into the workforce. And I did that for about a year and just felt like there's no fun to be had in financial services anymore. So much happening in San Francisco and tech at the time, and so, um, I said, as long as I'm reinventing myself, I may as well try tech and,

Wes: Yeah, I was gonna say, so you're talking like 2011, so like Facebook came out what, like 07, 08, the iPhone came out around the same time, so like Silicon Valley's just sort of carving its little space on the map at this time, right?

Elizabeth: Absolutely. And it was very different. I think today, you know, being in the space and certainly post pandemic, people are a lot more open to career breaks. People are a lot more open to people working remotely and all those things. But in 2011, you know, It was an old boys club. And I, you know, I, I actually, I actually joke with a lot of my friends, um, you know, when I was in the investment industry and I was giving a presentation for 500 Merrill Lynch brokers and in, uh, downtown Boston, you know, I was the only woman in the room.

They were all white men that looked like my dad. And then I move into tech and I'm the oldest person in the room. So there's a lot more diversity, but you know, it's, it, there's a lot of ageism and whatnot, you know, there, Most of my CEOs and bosses over the course of the last decade plus have been younger than me, substantially, and so

Wes: No, it's great. I mean, I think for you to come off of 17 years and want to get back in the workforce, I mean, I'm sure there's a lot of people out there that have a lot of anxiety or like, but you like have no tech experience in Silicon Valley where like tech is, you know, the birthing of all these great companies.

Like what led you to that? Like, did you just wake up one day and you're like, huh, this is a really uphill, big uphill bat. Like what, what led you down that path? It's, it's interesting.

Elizabeth: Yeah, I mean, I, you know, first of all, I said I got that first job on Craigslist. That was my first job. job with benefits and everything. You know, I did some kind of temp work and, you know, I was trying, it wasn't easy, I was trying to get back in, you know, and so once I landed that job, I was in the city and you feel the energy, you know, at that time in the city.

I mean, San Francisco was a fun place. You know, there was a lot going on. It was very youthful. It was, um, a lot happening. And I knew if I were to stay in the investment industry, not only has it become so regulated and, And so different than it was 20 years ago. Um, you know, I'd have to re sit for all my licenses and so many of the jobs that I would want to do in sales and go to market or on the East Coast.

And I didn't want to move back to the East Coast. And, uh, it just felt like a good thing to do. And, you know, in my early career, I had done inside sales, External sales, sales training and development, sales leadership. I found my first job in tech and sales ops, working for a healthcare tech company. And I know they hired me for, really for my sales enablement experience and, um, I was the only person at that company that wasn't, um, didn't come from healthcare.

Um, and you know, it was fascinating. I was employee number 29 there and, um, You know, they, the biggest reason people don't hire people for a career break is they think they're out of touch with the tools and whatnot. Right. So, um, one of the first things I did is I went to the Salesforce conference that happens in San Francisco.

There were 150, 000 people, it's Dreamforce. And I literally parked myself at the genius bar and learned everything I could and demoed every product on the expo floor. And I was just a sponge that year. In that sales, you know, sales ops role. And, um, unfortunately, like a lot of startups after a year, they ran out of funding and went bankrupt.

And so I found myself in a job search, but at this point I'd already broken the barrier getting into tech, right? And so, um, I was able to find an IC role just, um, in a sales role working for HelloSign and, um, I spent four and a half years there. So that was a great run. We were acquired by Dropbox. You know, I moved into leadership.

I. Um, you know, I was about probably employee number 40 at HelloSign and, um, the, the VP of sales who hired me knew that I had a lot, I was very different than a lot of the people on the floor, a lot of SaaS sales dudes and whatnot, all very good friends of mine, really, um, great people. And, you know, I learned a lot from them and, and, uh, you know, hope I was able to teach a thing or two, you know, coming more from the enterprise relationship building.

Carrying a bag kind of sales approach to them. And, um, but the, the VP of sales recognized I had a lot of experience. So he, you know, he, Let me represent sales in the weekly marketing meetings. I learned everything about the funnel and, you know, I worked with the product team to help, uh, prioritize, you know, requests that were coming in for, you know, product roadmap.

And so I got a lot of experience cross functionally and then moved into leadership. And so that was a really great run, four and a half years there. And after we were acquired by Dropbox in, gosh, I want to say it was February of 2019. And, you know, as happens after an acquisition, people peel off and the VP of sales left.

And then I was running the whole, pretty much the whole sales organization, reporting to our COO, Whit Belk, who'd come from Box and did that for about a year. And then just felt like, you know, when, once you're, you know, the integration into Dropbox, which is super fun. I mean, that Dropbox was, uh, very, um, Kind of typical tech culture, you know, with the Michelin star chef, three meals a day and all the things, you know, and so that was, that was kind of fun.

And then, but you know, I'm a mom. I like wearing a lot of hats. I I'm good in the startup space. I like building, I like growing, I like solving problems, chaos, implementing, you know, process. And, and, you know, that's kind of what I'm skilled at is, is that stage. So I ended up leaving and going to a very, very early stage startup.

Um, and in March of 2020, that didn't work out too well, but, um, you know, right, right at the pandemic. And then, um, and then I found another, another company, uh, called Pluma, which was another really fun run. Um, I was there for a year. I, I, I, The VP of sales, uh, I mean, sorry, the CEO was incredible. Very, very smart, um, you know.

Uh, Yale undergrad, Harvard MBA, and she hired me, um, in December of 2020. I, she offered me the job and I started an hour later because she was leaving in three, three weeks from maternity leave. And, uh, she came back in mid January and said, I just had this beautiful baby. I don't want to work a hundred hours a week as a founder anymore.

I want to sell the company. And so I w I had only been there about five weeks. And so I was disappointed in that, but we, um, it was actually a Great experience. We had 20 people in the U. S. 12 of them worked for me in sales. We had no marketing, no SDR team. We took it from 4 million to about 11 million in a year.

Wes: well, in one year

Elizabeth: Yeah, a hundred, a hundred percent outbound enterprise. Um, but it was, and we ended up getting acquired by Skillsoft, but that was a great, great experience for me too, because I was, along with the CEO and the CTO, it was the three of us on the leadership team. And so I was involved in the due diligence for the acquisition, which I had not been at HelloSign, you know, because you've got to be senior leadership, you know, those things can be very quiet.

And so that was interesting.

Wes: It's gotta be cool to experience that time and in Silicon Valley. Cause you know, me being in Michigan, I can only like, you know, fantasize like what that time was, but I just imagine like a lot of people, a lot of kind of like trading cards, like people jumping ship, getting poached. And so many, like to your comment around that company went bust or they ran out of funding.

I mean, it was every company there just getting pumped full of rounds of money. And I mean, was there any bootstrapped entrepreneurial companies that. Came out of there that didn't take a bunch of seed money or like anything out of that, that, you know, really sticks out to you.

Elizabeth: Yeah, well, so, um, HelloSign was a Y Combinator company. Um, so was Dropbox. So once we acquired, you know, it's interesting when you come out of Y Combinator, which is sort of the elite, uh, You know, accelerator for, for early stage startups. So you see that there is somewhat of a formula, uh, that, that works.

And, um, you know, so I, I worked for three Y Combinator companies. So that was, um, a great education. Um, we did get our series B. I mean, I, Joseph Walla, who was the CEO of HelloSign and Neil O'Meara, the CTO and Whit Bauch, who was the COO. You know, they, they, I learned a lot about what to do, right? They. They did get funding, but they were very conservative in how they spent it.

You know, we were, we were a frugal startup. We weren't doing the, you

Wes: One Michelin star versus

Elizabeth: I remember, yeah, I remember, um, God, I have a photo of it somewhere of our C, CEO, uh, Joseph Walla. When we were in this, we moved offices a few times, you know, and this is shortly before I started, uh, or I mean, after I started.

So I would, you know, again, I was employee 40, 40, 40. there. And, um, we got a, one of those, um, refrigerators for the office, you know, where you can actually have drinks in there. And I have a picture of him like looking at this refrigerator, you know, it was like, Oh my God, we've gotten a refrigerator, you know, just so that we can have drinks.

It was, you know, um, so, you know, it, it was fun, you know, the, the ping pong and all of those things. And, um, You know, we had a good culture. I think what, when you talk about Silicon Valley and the energy there, what sticks out to me the most is the caliber of the talent. It's unmatchable. And, you know, I, um, I like working remote.

I've, you know, I was a field salesperson when I was wholesaling back in the day. So I know how to be effective working remotely, but, um, you know, it's, it's, I wouldn't be where I am today had I not had that experience of working in the San Francisco area during that time period. Because it's a lot of like, you know, HelloSign was an engineering based e signature company.

You know, we'd go out and we'd pick up a salad at lunch and you're sitting at the little picnic table in the office next to engineers and having conversations and talking about getting into conversation. I mean, we were e signature APIs, but, you know, talking about, um, the moral decisions that engineers have to make when they're programming cars and, you know, just having the experience of.

being surrounded by that caliber of talent and learning and growing and sitting side by side. I didn't even know what an API was when I started at HelloSign and, you know, pull, you know, just pulling engineers into my sales calls and sitting with them and learning. And, um, you know, I learned how to do, you know, a few.

Calls, you know, and whatnot as a coder, you know, but nothing, nothing crazy, but you know, the caliber of the talent is really what is unmatchable

Wes: is that wave still there? Is it like, is it just the landscape completely different now?

Elizabeth: You know, so I moved down to San Diego. I think I shared with you last October, um, you know, but I think it's still there. And, you know, I've asked post pandemic, uh, a lot of people left. Um, but post pandemic, I was going to some in person events that were much more intimate, you know, like a couple of founders I would have, you have more access to founders that are still there.

I, um, I think a lot of the people that are left were probably younger people who were renting and it's a very expensive place to live and realize they could live at Tahoe and still do their job, you know, or go back home to Michigan and still do their job. Right. But, but so it kind of left a pool of founders.

I mean, I know a lot of pretty incredible founders. There's also, um, one thing that I'm seeing in the Bay Area is, um, Um, and it's actually not even so much down in the Silicon Valley or in the financial district or in South of Market. I think it's kind of in the Hayes Valley area. There's popping up the whole kind of AI

Wes: yeah,

Elizabeth: home spot, you know, and, you know, just, just, and you can't, you cannot replace in person meetings, you know, and like going, going to coffee with, you know, friends of mine who are AI founders that.

That worked down there. And I worked for an AI company. I was VP of sales for an AI company for a year. And, you know, it's, um, going to the after office, after hours talks and things, and getting invited to these little dinners for AI companies and thought leaders, and, you know, you learn a lot there and, you know, I do think places like Austin and Phoenix, and I'm even seeing a little bit of San Diego.

There's a founder community down here that I've really I've been tapping into and having fun, you know, I think, uh, it's become more and more, um, entrepreneurial down here in, you know, from everything I'm hearing since I've been here in October, but it's not the same. It's not the same.

Wes: It's funny, a realtor friend of mine, there's like a subdivision a mile, mile or so for me, and it's in a gated community. He said that he had a couple come from Silicon Valley, like she had family here, he could work remote, and they were looking at this house. It's probably like a million and a half.

And they didn't realize that it had a basement, and the basement was like 3, 000 square feet, and then they saw the price of the house and they thought he was lying, and they were like, you know, we could probably take two or three of these houses, just the value of homes in Michigan relative to what they were talking about in San Francisco was just

Elizabeth: Yeah.

Wes: dropping, um.

Come here and live like a King. Um, but that's, that's interesting. So like thinking about that moment in time, like you had mentioned that you just sold your last company, you're coming out of a sale, like, how did that come about? So you work for Hello, um, you work for HelloSign and then that transitions.

And at what point do you say, Hey, like, I want to do my own thing. Like, how did that come about?

Elizabeth: Yeah. So I, um, you know, I left HelloSign in, I think it was, I February of 2020. Um, and, you know, I went on to, um, be the VP of sales for, uh, that early stage startup that failed. Um, and that was a legal tech company. It was just too early. Um, and, uh, I went and worked for, um, Pluma that was acquired by Skillsoft.

And that was, I learned more in that year than I learned in four and a half years at HelloSign. I mean, it was just a, it was, um, just an incredible experience. And then, uh, and I'd still be there if we hadn't sold. Um, but then I was at Skillsoft, which is, you know, a big, Company again, once again. And, um, I got a, I got recruited to become the VP of sales of this AI company, uh, nato.

And so I went over there and I worked there for a year. And, you know, I, I found myself working 80 hours a week and I had three days off and, you know, I just kind of felt like I, this is too much. Um, so at the end of 2023, I decided that I wanted to go off and do my own thing and, um. And so I started doing the consulting a little bit.

And, um, I was working with, uh, the thought leader, Scott Lease, if you know who he is on kind of coming up with multiple sources of income and, you know, becoming unplugged and untethered as you would, would call it. Right. And, um, and so it was, I guess it was February or March of 2023 that, um, a There was a CEO out of New York who, um, in 2020, he lost his Director of sales and he ended up with his whole sales team reporting to him.

And so he built this slack app To help him manage his team and keep them engaged and it saved him 10 to 15 hours a week And it's got it and it increased their activity And so he came looking he just organically put it out there and got some customers and he was using it You know, he built it for himself.

And so he came looking for a co founder Last year and and we were connected and I just loved the product. I'm a I love the idea of the product I'm a mom, you know, I have three adult kids. My oldest is an SDR And he's, uh, he works in the office three days a week, but I see like a lot of his friends, you know, this remote work, I believe in it.

It's great. But when you've come out of school post 2020 and you've never worked, you've got to have a lot of motivation, right? It's, you know, and my son knows himself well enough. You know, he, he, uh, you know, he's in the Bay Area, which is great. You know, he'd, he'd love to move down here to San Diego. One of my other kids is down here too, but he knows he can't work remote, you know, he's, he'll be surfing and, you know, playing video games, you know, you gotta, you gotta have, you have to have a certain work ethic, right?

And so the whole idea of this product that we built was, or that my co founder built really was, um, you know, to help team engagement that, that is remote and hybrid and, um, and But, you know, the, the way the tech market has gone in the last year and a half, I didn't want to get funding. We were bootstrapped.

I didn't want to, I did not want to get funding because I know too well how having investors changes expectations

Wes: like, what specifically with that, is it, you know, as a private equity or like new management teams come in and just change that culture or like what's,

Elizabeth: Yeah. I mean, as a VP of sales now for multiple times, right? You're involved in board meetings and whatnot. And so, you know, I've had to, to report on revenue and all of that to high profiles, you know, VCs. And, um, you know, I just know the expectations are different, you know, and, um, it just changes. In fact, that very first tech company that, um, that I worked for when I was RevOps.

I, I mean, I, I wasn't on the leadership team, so I can't speak to it. You know, we had had a 14 million raise and ran out of money, um, but pre revenue. But, um, you know, I, from my observing, I mean, I think one of the problems was, is the, the, um, VCs there, I could see the leadership team spending a week, a month creating reports for the investors.

And that's time when you're not building the company.

Wes: yeah, yeah. I was going to ask, like, what, you know, what do you, uh, like, how does the company burn through 14 million of funding? Like, where do you see most of the ways going?

Elizabeth: yeah, that, I mean, that, that, you know, and that was a lesson to me in, you know, I had this philosophy, um, Wes, where I literally like, but even before I was a CEO, I'm the CEO of my own life, right? You want to bring in more than you spend, right? You want, you know, you want to, you've got to manage responsibility.

So. And you know, this company was, uh, um, there was a 14 million raise. It was pre revenue. There was no revenue. And we had a beautiful office space in the Embarcadero.

Wes: Which doesn't sound cheap. Doesn't sound

cheap either. So

Elizabeth: At that time, no. And, you know, um, it was just me and the office manager because the CEO and the chief sales officer were traveling around, you know, to visit.

Potential customers most of the time. And, you know, that was wasteful, right? There was just flying here and flying there for meetings that probably could have been virtual and, you know, it, it was, there was a big high spend.

Wes: fast forward to like where you're at today, like your, your consulting company, are you now, are you focused more on, uh, you know, enterprise level companies, like in the Bay area? I mean, do you cling on to entrepreneurs or what's sort of your, where do you like to spend the majority of your time?

Elizabeth: Yeah, well, so a good question. Cause I've done a lot of enterprise sales in my career, right. But, um, really where my expertise is, is building and so where I found my niche and, you know, I think really what. makes a lot of co founders, a lot of startups fail is sales, right? It's, and, and one of the biggest mistakes, you know, and this is the interesting thing too, I've worked for many CEOs who are very, very smart.

You know, they're coming out of the top schools, Harvard, you know, Stanford, MIT, Cal, um, they all come, not all of them, but many of them come from the technical and product side. They all think the product is going to sell itself. It never does. You know, and, and, uh, in this is a generalization, but many of them don't respect the sales function.

You know, they don't, they're kind of allergic to technical people. I mean, I've sold to developers and engineers, you know, by, by nature they're allergic to salespeople, right? So it's, um, you know, it's, it's a very different kind of leadership, right? And so. Um, a lot of these, these founders might be very good at selling the product themselves, but their biggest mistake is their early sales hires.

They either hire VP too soon thinking they can just scale it. They hire, or they hire early stage sales people who don't know how to sell. And, um, so really what I'm doing is I'm trying to help. These founders who are doing, they have to have founder let sales. I won't work with anybody who hasn't at least sold five or 10 deals on their own, you know, so, um, but so they, they know it works, but they can't get it out of their head into a process to make it scalable,

Wes: Is it because like, that's not like I look at, so I'm just, I'm an entrepreneur, strip me down. I'm an entrepreneur, but I've been on this kick around, you know, what's the top three things that you're best in the world at. So are you referencing that they're just not best in the world that sales are best being tech and product?

Um, and just get them focused on there.

Cause I

think as a founder, you're wearing a lot of hats, right? And

Elizabeth: yeah.

Wes: if you're on the tech, you're on product, you're on sales and, you know, tech and sales are, you know, to me, two very, very different things.

Elizabeth: Right. And even if they are good at sales, I mean, and some of them are very, very good at scale sales, they can't sell all the time. Like they, if they want to grow the business, they've got to duplicate themselves.

Wes: I'm stuck in that right now, myself. I'm the second company.

Elizabeth: Yeah. Oh, I'm happy to help you. We can talk about that. But, you know,

Wes: that's great. Like, that's a very specific thing, a very specific gap that you're filling. So what does that look like? Like, how do you now get into a room with a CEO to make them realize like they're the problem and they need to get out of the way and like, cause they, I would imagine that they have to be in a position of like, I'll listen.

I know that I'm the bottleneck. I'm the problem and I'm ready to make a change.

Elizabeth: Yes, and they do. I mean, they come to me typically, right? They know, like, they know, and you know, I'll go where I'm getting most of my opportunities, although a lot of my opportunities are coming from a few VCs that I know that have portfolio companies that need help, you know, so that's been a, that's been a good funnel for me, but I'm finding um, Ironically, I have had some interesting experiences recently.

I had a chance to go to Necker Island with 30 entrepreneurs and Richard Branson, which was really very, very cool experience. Um, but I met, you know, a lot of entrepreneurs and I've found a few people like yourself, like, you know, that, I mean, business owners in different areas that are having that problem.

And so there's one person I'm working with who, um, you know, I'm helping her build her playbooks and everything. And she runs a publishing company, you know, and another person that runs a marketing company. And, you know, so I'm learning that actually this wasn't, you know, I was thinking it was just tech companies, but I'm finding, um, small business owners or midsize business owners are needing help building their infrastructure.

And what I do is I come in and I'll do an audit and I audit the people. The processes and the positioning. and you know, there's a lot of areas that fall under that, um, you know, and so I identify where the weaknesses are, you know, and uh, you know, some, some companies, they don't, they've never had sales function, you know, some people, um, you know, and I help them identify what their ideal customer profile is, what their, um, Elevator pitches, you know, what they're, and then I can come in and I can put sales processes in and evaluate their tools and how they're outreaching and, you know, um, sequences and so many, so many areas.

Wes: do you feel the biggest objection is like for a CEO that like, you're like, they, they need the help, but they just can't get out of their own way or is it just sound too overwhelming or is it take a lot of work on the founder or CEO to like, you know, actually make that shift where they're just scared or, you know, it's just too comfortable where they're at and they just don't want to invest the time and effort.

Elizabeth: Yeah, I mean, they, they have to want to grow. You know, usually it's like they just haven't been able to and they need help. And, and usually the ones that come to me, they're, they may have had a couple of bad sales hires, like a sales leader, and they're afraid to make the commitment again, right? So, um, so what they can do is they can de risk that by, by hiring me.

And I come in, I usually typically have a minimum of a three to six month, um, engagement with them and, um, and so that I could come in and I can do the whole evaluation as almost kind of like, you know, I give them the, that high quality growth expertise without the commitment. It's like almost like fractional CRO work.

And I can do that as well, but you know, the difference between consulting and fractional CROs, fractional CRO typically comes in for a fixed CRO. And I can certainly do that too. But, um, you know, what I'm doing is, is really kind of more on a Go to market consulting and advising capacity where, um, you know, I can help them build the infrastructure and the foundation to, to scale the organization without having the commitment.

Wes: Are you shy? Like, are you blown away sometimes when you like take a peek under to see what companies are working with and how they've gotten to a certain point? Like without structure, without process? I mean, is it, I've seen a lot of entrepreneurs, like some companies that are a million, I've got a couple like at 80 million and there's like zero processes in place and you know, they're like, all right, we're ready to, uh, you know. Put these things into place. It's like, wow. Okay.

Elizabeth: Yeah. I mean, that's an ideal situation. You know, that's a, that is a, Slam dunk for me to come into companies like that. You know, I was just talking to a CEO. He's got 20 film, 25 million in revenue. Um, and as wants to scale, you know, and that's perfect for me where, where it becomes a little more challenging is, you know, and this tends to be more the tech founders where they haven't really had a lot of success on their own.

And they want you to come in. You know, they might be sub 100, 000 in sales.

Wes: wow.

Elizabeth: And they want you to come in. They want, you know, they're looking for the magic bullet. They're looking to pull a rabbit out of a hat, you know. And, um, I've, you know, I've, I've had, you know, I've had, I get people reaching out to me every week.

These, you know, leading, you know, CEOs from AI companies that like, can I just pick your brain, you know, and I'm like, sure, I'm happy to do some consulting for you. And they're like, well, we don't have any money. We just want to know how to do founder led sales. I'm like, well, good luck with that. You know,

Wes: Uh, so in terms of like, so an AI, like what, you know, what do you see in like the next 12 months? Like if you're a small business, like what should you be thinking about? Is there certain things you should be reading, researching? Cause it's so overwhelming right now. There's so much information. Companies are popping up overnight.

You know, do you have any like great experience share advice for small businesses and how they can start to like, think about AI logically for their business?

Elizabeth: So, um, yes and no. Um, I, you know, I, I know the space very well. I, um, I have some very, very close friends who are CEOs that I respect to the end of the earth of AI companies that I, you know, talk to regularly. I, um, I believe wholeheartedly that, um, Companies need to adopt AI or they're going to be irrelevant.

Um, you know, it needs to augment your, you know, your functions in, in order to, to help you grow faster. Um, at the, the other end of it is I left AI in end of December of 2023. So a year and a half ago. It is. Lightyear's different. Chat GPT came out right after I left. Right. So I use it all the time, you know, but, um, you know, you should be using it, but you know, it's changed.

It's

Wes: what's crazy is somebody asked me the other day, they're like, Hey, I, I've kind of embarrassed to ask you this, but like, what is chat GPT even do? And how do you use it? And. Today, actually, I had somebody that wanted to meet that wanted me to sign an NDA. And it was like 14 pages long. So I just copy paste, put it in there and ask, like, is there anything I should be worried about?

Like, it's got all my information from the conversations I've had. And it's like, you know, I brought up two points that you may want to get this in front of your lawyer, but it's very generic and, you know, I kind of trust it. Like it's, so it's just interesting that, that. And it does so much more. I mean, I know the imaging and Canva and all these other, you know, it's a little, it's still a little off, right?

Like you asked it to do something, you know, add like eight fingers and misspell words, but. pretty scary right now. Like what you can produce, um, and what you, the information you can get. Um, so like what, what type of opportunities are good for you? So like, if there's anybody out there listening, that's like, yeah, I mean, from my experience, entrepreneurial focus, I don't really spend any time in enterprise.

It just doesn't interest me, but my entrepreneurial sphere of influence, it's always sales challenges. Like that's never ending. There's always something. Um, you know,

Elizabeth: Yeah.

Wes: Yeah.

Elizabeth: Yeah. I mean, I, you know, I think anybody that's having any challenges with sales. I mean, I'm happy, happy to have a conversation. Um, you know, I have a website, uh, actually I have a giveaway, a freebie on my website. Um, I just launched my website because I'm now, Full time entrepreneur now for the last two months since selling sales can be right.

So, um, I'm going at this full time. So I just launched my website, um, and I have a free sales playbook template. It's pretty high level, but, um, I really think it's helpful for, um, you know, small business owners or founders that, you know, kind of want to think through like what are their product offerings?

What are their, what are the, what is the low hanging fruit for their target? Um, you know, profile that they're going after. And, um, you know, it can kind of walk you through some of the basics there. That's, it's pretty high level, but, um, you could certainly go to my website, uh, and schedule time for a consultation or a conversation.

I'm happy to talk to people. Um, the website is ElizabethAndrew. com, no S, so ElizabethAndrew, uh, com. And

yeah,

Wes: awesome. I did download your, uh, the download and it is super helpful. It makes you think right. And I think that's as entrepreneur, like you just have to think, challenge yourself, work on the business, pull yourself out, bring in experts. You know, you have a wealth of knowledge and I mean, the SAS, a reoccurring revenue model, like all those things are really important for entrepreneurial companies.

Um, or is that the easiest way for people to get ahold of you? Is the elizabethandrew. com, um, LinkedIn,

anything like that? Yeah.

Elizabeth: I'm also on LinkedIn. Um, it's actually Elizabeth A. Andrew. Um, so two A's there if you, or you could just Google Elizabeth Andrew on there, you know, but, or, but, um, you know, the, the actual, um, URL is Elizabeth A. Andrew on, on LinkedIn, but yeah, and I have a few offerings too. I mean, I, you know, depending on where people are, you know, my, I do sales consulting where I can come in for a minimum of a three to six month engagement and I go all in and I audit and I, you know, um, you know, and, and if you're hiring a VP of sales, you know, it can be four to 500, 000 a year to hire a VP of sales, right?

So it's,

Wes: Is that something you'll help out with? Will you help the founder, the CEO, you know, write the job description, find the right type of person?

Elizabeth: Absolutely. I help with hiring and I don't charge four or five hundred thousand to do that. You know, it's, it's a much smaller commitment, you know, if I'm doing full consulting. But, you know, there's some companies that maybe you're afraid to commit to that. And I can do, um, you know, I could do more of a, um, coaching for the CEO and, and coaching them.

And, you know, Make it, you know, an hour call a week, um, or I can do advising. Uh, you know, I do advise some companies and, um, so,

Wes: Well, that's awesome. Well, Elizabeth, I really appreciate your time. Uh, you got a great story, a lot of experience and again, Elizabethandrew. com. Download the free, uh, guide. I did. It's great. It gives you a lot to think about. And if you're looking for, uh, you need to say, if you have sales challenges or need to kind of clear your head as an entrepreneur, uh, Elizabeth Andrews, a great resource to do that.

So thank you so much for the time and coming on. I really appreciate it.

Elizabeth: Thank you so much for having me. It's so great to, to connect again. And, um, yeah,

Wes: right. Well, well, thank you so much. We'll, we'll talk to you soon.