Clover: Conversations with Women in Leadership - Founders, Executives, & Change-Makers
Clover is a podcast spotlighting women who are redefining leadership. Hosted by Erin Geiger, the show features founders, executives, and trailblazers who are reshaping the way we think about success, work, and life.
Each episode dives into real conversations about the wins, the challenges, and the bold decisions that drive women at the top of their game. From scaling companies to leading teams, breaking barriers to driving change—Clover uncovers the stories and strategies that inspire possibility.
The name comes from the phrase “to be in clover”—to live in prosperity, comfort, and joy. That’s the spirit behind every interview: empowering, honest, and full of takeaways you can bring into your own leadership journey.
If you’re building a business, leading with vision, or simply seeking stories that fuel ambition, Clover will keep you inspired and equipped to grow.
Hit follow to join us each week as we step into abundance—together.
Show artwork by the incredible Mayra Avila.
Clover: Conversations with Women in Leadership - Founders, Executives, & Change-Makers
From Startup Chaos to Scalable Growth: How to Win the First 5 Years with Stephanie Quay
In this conversation, I catch up with longtime friend and operator, Stephanie Quay—a five-time acquisition veteran who recently launched Five Experts, a platform matching early-stage companies with proven operators to drive value creation in the first five years. We trace her zig-zag path from film school and TV.com (hi, CNET days!) to growth-stage leadership across PE- and VC-backed companies, and the playbooks she now packages for founders, investors, and fractional experts.
Stephanie opens the hood on the 5×5×5 framework—from the first 90 days through year five—and how to pull the right levers (margin, operations, capital efficiency, customer success, revenue) without losing your culture or your North Star. We also get into what makes someone an expert (outcomes + the ability to teach), why “warm demander” leadership works, and how to protect your focus by controlling what you can (sprinters, we see you).
What you’ll learn
- How to diagnose growth inflection points in the first five years—and what to do in each phase
- The 5 value levers that move EBITDA (with real examples from PE-backed turnarounds)
- Why breaking apart sales vs. customer success can unlock outsized growth
- The difference between experience and expertise (hint: repeatable outcomes + coaching)
- How to set a clear mission/ICP so teams row in the same direction
- “Warm demander” management: high standards + high support
- Mindset for founders: doubt is normal—return to your mission fast
Who this is for:
Founders, operators, and investors navigating resource-constrained growth; women in leadership building high-performing teams; and anyone curious about turning career zigzags into a superpower.
Connect with Stephanie:
- Five Experts
- Email: growth@fiveexperts.com
Favorite lines
- “An expert has proven the outcome—and can teach the path back.”
- “Culture and mission aren’t posters; they’re the daily operating system.”
- “Control the controllables. Ignore the rest.”
Hey, everybody, welcome to the latest episode of clover. Really enjoying having these discussions, these conversations with women in leadership. And this week we have on Stephanie quay. We go way back. We were just talking before the episode. We started recording on how long we've known each other. It was a little scary, because it means we're a little older now too. We're gonna pretend that's not the case. Stephanie has she's about to launch, or by the time this episode air, she will have launched, which is so exciting. Her newest labor of love, five experts. But before we jump in, Stephanie, just first of all, welcome to the show. So excited to have you here. Thank you.
Unknown:Thank you. I know, and we go so far back. It's, it's amazing. It's scary, but it's, it's amazing.
Erin Geiger:It's very cool, like, when you can look back and be like, wow, you know, to have these relationships, you know, with other women in this sense, it's, it's, it's pretty great. Not everybody has that. So pretty grateful. So let's just jump in stuff, if you wouldn't mind, kind of, I always love hearing like, kind of like people's like, origin stories, their career journey, how they started out and how they got to where they are today. I think that's really helpful to our listeners as well. We have a very variety of people who listen to this show. Some are just starting out. Some are pretty seasoned. But anyway, would love to hear your trajectory.
Unknown:Yeah, absolutely. So I think probably, like any career, my path has not been a straight line. It's zigzagged, and definitely have not ended up where I thought I would when I first started my career, like I think most people, but that, in and of itself, has given me the range I feel like to be able to do what we're doing next. I actually started out in entertainment. So I went to film school, Emerson College in Boston, grad school at NYU. Thought I was going to make a path as a producer, and completely shifted once I dove in and figured out what I was a little bit more passionate about, which was the conversion of technology way back in the day with entertainment. So made that path and went to a company called tv.com which was owned by CNET networks. And that's where you and I first met, and that's really where I feel like I learned my first taste at negotiation. You probably remember back in the day it was when ovis is going to date us. I'm sorry. It's like way back in the day when content was not available. TV shows and films were not available online. You couldn't like go to YouTube or go to netflix online and actually watch whatever content you wanted. It was it more of a what I if back then, and you probably remember, we streamed the first episode of The Office, yeah, yeah, as well as the red carpet of the Emmys and those Two opportunities where we were really like transforming the way an industry was going to shift really moved my passion for early stage companies and how to really transform those companies into transformative within an industry. So it was, it was there that I then kind of moved down the path of going to more growth, stage companies, early stage companies, building out those negotiation chops through managing sales and business development, which has led to five different acquisitions. One was, I count one tv.com for CBS interactive and the others. Three other were VCs. One was my own company, and more recently, one was private equity, and that those acquisitions really led me. To five experts in what we're building today. No, it's funny how,
Erin Geiger:because we both actually started out at Entertainment, both went to film school. Yes, it's funny how our life can take you. You've been part, like you said, of around five companies that have been acquired. And you know, with that comes so much experience and growth and scaling. How have each of those experiences kind of impact your your view on that, especially since, as you've mentioned, we've been around the the bend a few times, as things have changed and you have scaled companies and different industries and how, you know, in a different innovations have have come around. I almost feel like that's almost like a passion for you. It's kind of, kind of coming in and seeing how you can grow something to the next level. So we'd love to hear your kind of your thoughts about that,
Unknown:yeah, for sure. I mean, I always, I love challenges first and foremost. So whenever I see a company that, to me, is always a challenge. How do we take this company to the next level? In terms of growth, every company will have a given outcome, especially an early stage company, and if it's venture capital backed, or private equity backed, or even founder led, it may have a different outcome that they're looking to achieve. But that being said, starting out with that problem and then looking at that outcome, I have a huge passion for building that path to get there, and so with the five companies that I was involved with, I mean, that's where I feel like I always started out, is like I came in to solve a given challenge or a given problem, and then I knew working With the leadership team, or working with the board and the investors, what outcome they were looking to achieve. Some times that's really clear, and sometimes it's not, and sometimes you have to put your insight in and your experience, and I feel like depending on how clear that outcome is, but that's mostly been a strong passion of mine, and what has kind of led to what we're doing next. I mean, examples of that are, you know, sometimes there's a founder and they don't exactly know who that ideal customer profile is. And so for that example, like I feel really passionate being on the sales and business development side, and go to market side, coming in and trying to help identify who that ideal customer is, I mean, that's just one example. There are hundreds of other problems and challenges that a growth company might have as it looks towards that outcome, and then, essentially, we built a framework for identifying those problems, matching them up with the challenges, and offering the given outcomes. Yeah,
Erin Geiger:and so, yeah. So let's talk about five experts, because I feel like you are you kind of built that blueprint, and you're helping others now scale their companies at a almost at a larger scale. Now you can impact multiple hundreds, you know, of companies as five experts grows at a time, rather than just kind of helping advising, you know, onesies, Tuesdays as you go. So let's talk about five experts like, what brought you to come up with, you know, launching such a company, what spurred it on, and tell us more about what five experts serves in the mission?
Unknown:Yeah, sure. So, like I said before, like, I'm always inspired by challenges and problems, and I saw a little bit of a hole in the marketplace, like I mentioned the last company that I was at, controller training solutions. I was there for five years. I've always been around employee 10 to 20 for any of these kind of growth companies I've worked with, and so early, early stage. And that one was unique and interesting to me because it was backed by a private equity firm, but more specifically, a search fund, which essentially just means a C. CEO comes in, matches up with an investor, and they buy a company that's already been in business. So cantola was a company that was in business for 30 years. Was launched in 1983 had rather stale growth, and the CEO and the private equity firm came in to buy the company, to grow the company at a more rapid rate so it could have a positive exit. And what I learned really quickly is that private equity is very different from founder led bootstrapped investing as well as venture capital. And one thing that I find was unique to private equity is this idea of a value creation team. So many of the private equity firms, small to mid size and larger as well have a value team of operators. These are proven experts that can come in and advise in different areas. So for us, for example, at cantola, we had a sales team that was in place for about two decades. They were doing full sales cycle, which basically means they were doing outbound sales, inbound sales, customer success, retention. There is no kind of upselling arm or ability as well. And so what I saw really quickly as a way to drive additional growth was to break up that team, build a customer success team, focus on outbound sales and try and maximize this team's time for selling where we could have and build another customer success fund. And so the immediate challenge I saw was, how would we build out that customer success function so we could maximize sales on the outbound side? Well, as I was managing that sales team, I also would not have the ability or the bandwidth to really build out a customer success team. So one, one of the things that the private equity firm we were working with really offered was an operator to come in and serve that function in a fractional capacity, advise us ensure that the culture was intact so nobody jumped ship. Everybody was happy we could build out that outbound sales arm, and then obviously build out the customer success side. Having that operator, that fractional executive, come in, was critical, and I think essential, to the value that we drove on the acquisition, so that, in and of itself, was really interesting to me, because I saw the value that expertise could provide to growth companies at these inflection points that really mattered. And that's something that we didn't necessarily have in other investment styles like venture capital, and so I sort of was sitting and thinking about this further, and thinking, What if every growth company had the ability to tap into expertise like we had, and essentially could have the playbooks that we had, which are those proven processes, the expertise, the actual human insight, who is someone who has done this before, and what if they could, together with those playbooks and the expertise really access every essential advisor they needed at a given time, on demand. And so thinking about that further, I decided that I wanted to take on building out that platform, and started that process December of last year.
Erin Geiger:That's exciting. And so how can you explain, kind of like how it works in practice, right? And how it's different from what you would traditionally see, like if and who you target also, you know, let's you know, what kind of companies do you support, and how does it all kind of come together for them? Yeah, sure.
Unknown:So first and foremost, we target companies in the first five years of their growth or investment journey, and that's why we're called Five experts. Is everybody on our platform has expertise working with companies that essentially need to grow in those first five years. Those can be venture. Capital backed early stage growth companies. They can be private equity backed. They can be founder led, but the common trait that they have is the need and desire to grow in those first five years. So what we've done is we've built out a platform where experts have profiles and have the ability to be marketed. We do that on their behalf as well. We have coupled those experts with a five by five by five framework of value that we really believe, if put into practice, we've seen it happen. Our our thesis is, if you put this into practice, your company will derive value exponentially on EBITDA growth, which matters quite a bit for the investment companies out there. And what that essentially means is five by five by five. The first five is the first five horizons of growth. So that's growth within the first, first 90 days of an investment. Those 90 days, those critical times when you know a new company is coming to fruition, or a new CEO is coming in to acquire that company. So those first five, those first 90 days, second that is year one, year two, year three and year four to five, we have a formula as an analysis where we look at where a company is within that growth journey. That's the first pillar we look at. Second to that. We believe there are five value levers that can be pulled, and those are margin expansion, operational efficiency, capital efficiency, customer success and revenue and growth. So we have playbooks downstream from all of those different levers. And then finally, we have seen that if a company focuses on five sprints within those different categories every single year of their growth journey, they will increase the value of their company exponentially and measurably. They will grow the company and have a more successful outcome in those first five years. That is tremendously interesting we have heard, especially to venture capital investment firms out there, because what's happening in the market right now for venture capital firms is that the holding period for the companies they're investing in is getting extended beyond those three or five year holding periods, sometimes to 10 years for two reasons. One is that IPOs are slowing down, and then the other reason is that the companies aren't growing at a rate that would have a successful exit in those first five years, and so we are tremendously exciting. We have heard to venture capital firms as well as private equity because if we can drive value in those first five years and have the successful exits that they're looking for, they can take that capital and reinvest in another company. If those holding periods get longer to, let's say, 10 years, they don't have the ability to recapitalize at a rate that they essentially used to when markets and the industry was moving at a more rapid pace.
Erin Geiger:So it's kind of like a win, win, right? So you're supporting on the VC side, they're like, great week, you know, we can see a return, you know, quicker. But then you're also supporting these founders who the first five years are tough so, you know, and they don't have the support, you know, regardless of how they're run, whether it's, you know, founder led sales, or what have you. They need that support. They don't have, they don't have the knowledge, you know, base to cover everything, right? And so that's super exciting. And I know that a lot of startups are going to, well, they should run with this, you know. And so I love that it's both, though it's like not just supporting the founder, but also supporting the VCs and those who support them, which is pretty genius and Okay, and so I'm assuming you've taken what you've learned. I mean, you've scaled, we've talked about it. You've scaled so many teams. And for those listening who are growing their careers, you. And kind of want to maybe take similar steps. What have you learned about building this such high performing sales and biz dev teams along the way and like, what from what you've learned, what can still be applied today? I think that could be valuable to a lot of people listening right now.
Unknown:Yeah, I think, I think there's two things. Is one, you always have to look for the win, win in any situation. So like, to your to your point, I feel like what we're building is a win for the investment firms. It's a win for the growth companies, but it's also a win for the experts out there. These are wildly talented individuals who have so much expertise to give and often get lost in the linkedins of the world. And, you know, don't really have a place to connect with the right companies. So I think building high performing teams or a high growth company or a high performing company, I think you always have to look for the win, win. I think you always have to also narrow down who is your ideal customer out there, and that's individually, like, if you're ever, even if you're looking for a job, what is your ideal customer being? What is your ideal job like? Maybe that's a stage and a size of a company. Maybe that's a company in a given industry. And so I think always looking for that win win, something that I think I've learned more recently in my career, but it was kind of always, always in the back of my mind is that culture matters so much when you are building a team and having a mission. And that goes for someone, I feel like individually, if you have a mission, and know what your mission is, it also goes for if you are a leader, if you're a head of sales, or a sales manager or marketing manager, someone on the product side, and you're managing individuals, it's what is your individual mission, and what is your team mission? Knowing that I feel like has the ability to rally individuals, put them on your train and be able to march forward to whatever goal you have. That goes for a CEO as well. I can't tell you how many companies I've experienced or walked into where the CEO is a little bit fuzzy on who their ideal customer is, and a little bit fuzzy on their mission. And I feel like if you don't communicate that mission and wake up every day saying, Okay, this is where we're going. This is what we believe in. This is who we are as a company, or even are as an individual. You won't be able to have the success that you want to have. And I think that, in part, is that culture building that I think is so important to building teams and working with individuals in a team is, you know, obviously having that mission, but then living it and breathing it. The other thing I think I've learned as a manager, my last boss that I had, the CEO of this company, cantola, called me a warm demander, which I always thought was funny to me, like as a manager, that's a little bit of how she coined my management style. But I think it's something that works really well because have high standards for yourself and have high standards for the people that are on your team. That's that demander part is like they are on your team because you believe that they can get the job done, and that's important for them to know and but also be there to be a support. Like, don't, don't have one without the other. Don't have the demanding part for even yourself, right, as an individual, don't, don't have that demanding part of like, this is all we care about, is the outcome of something. Be a support to yourself and be a support to the people that you're working with, and good things will happen in the end. Yeah,
Erin Geiger:no, that's so true, and it's to your previous point. Your North Star shouldn't change every day. You should always be marching to. The same. And then a lot of your decisions can then come back to that. It's like, okay, well, is that fulfill the mission that we're we're working toward? And then to your other point of leading, you know, kind of like that warm demand. It's a Yeah, because you also need to, like, I love the quote, If serving is beneath you, then leadership is beyond you. I think that's another way you know so totally agree with that. And as you're looking, as you're working with, you know, you've worked with so many different founders, and you're building a platform to serve them, as well as the the experts in the VCs, what have you seen about misconceptions founders might have as they embark on these early years that are typically resource constrained and budget constrained, like, what have you what have you seen out
Unknown:there? Oh, boy, where do you start? Oh, my gosh. You know, enjoy the I think, enjoy the journey. I think that's one thing that founders may forget as they go deep into the weeds of wearing 700 hats and every day, wake up and it's like, is it going to be a chaotic day or more of a calm day? And so I, I think, enjoy the journey. I, I would also say one common theme I find and and I even have it within myself. Every founder has that moment of doubt. You know, every single founder that I've encountered has sat there saying, Oh, my goodness, what on earth am I doing? Like, why am I doing this? And that comes back to like, making sure you know what your mission is, and reminding yourself it's okay to have doubts as an individual too, right? Like it's okay to have doubts, and you're going to have those moments where you sit there and you're like, am I absolutely insane for going down this path? Should I have just got, gotten a nine to five job, and like, you know, I have family and kids, and what have I done that's, you know, absolutely normal. So think about that and say and recognize and say, okay, you know, to other founders out there, I would say, recognize it, know that it's not unusual. It's very common to have those moments and then go back as quickly as you can to what your mission is.
Erin Geiger:Yeah, yeah, agreed. And so in addition to the founder aspect you did mention, like you're kind of also supporting these experts, who are then therefore supporting the founders. So what in your mind? What's the difference between an expert and someone who just has experience?
Unknown:Oh, and an expert has proven an outcome before. In my mind, an expert knows, and also an expert knows the path of how to get there and can communicate it back. But to me, experts always have the path and the outcome in mind. You can have experience in something, but you may not be able to come back and teach that experience to others and really like advise. It's that bridge between having experience and being able to advise on it,
Erin Geiger:right? Yeah, and I think the outcome is a big piece of that, right? If you're experienced and you're just, you're still kind of on that track, right? Of gaining that experience, that's one thing, and with another thing you know, to your point of, once you're reached, kind of like that unlock the expert level that it's more of like, okay, I've proven, you know, these hypotheses, gotten this outcome, and I can then, you know, turn around and teach others. So yeah, I like that description. And what's like, sorry, go
Unknown:ahead. Oh, I like what you mentioned before about serving as well, because I feel like there's for experts in my mind. There's an act as for experts in my mind, there's an aspect of coaching, of serving and giving back. It's. A little bit more than just sitting back and saying, I've done that before, like you have to take the next step and go to the next level of yes, I've done that before, but I can coach on it. I can give back. I can serve the given outcome.
Erin Geiger:It's almost like it has a flavor of mentorship. It does, yeah, okay, yeah. What is your vision for five experts, like you're about to launch right the most, one of the most exciting parts, and thank you for even taking the time, because I know you're insanely busy right now, but you know, it's so and I love it too, because it really is about the founders, like giving them access to guidance, you know, and kind of give empowering them to be like, Oh yeah, I need, I need, I need support in this area. So I'm just curious, like, what is that, that big vision that you have for five experts, as you continue to build,
Unknown:you know, it's all about it's all about growth. You know, for us, the more companies out there that we can follow provide the guidance and expertise to have successful outcomes, the better. I view us as sort of this new version of a growth ecosystem where we provide all aspects of value creation on demand, quickly and easily, and provide value really to you know, like I mentioned before, everybody in the in the growth equation. So the experts, the growth company, the investment firms, we have some exciting partnerships coming up that we will announce in the next couple of weeks that are in this growth equation, that are tangential to us, that are more strategic in nature. But if we can really become that go to place for value creation, allow investment firms to extend their value creation teams. And you know, I envision if we can take up even 10% of the market, we'll be building job creation just based on that growth for hundreds of 1000s of people. And that's really my vision as well. With job loss and the economy going in a lesson positive direction, as some might say, like that's that's something that I feel passionate about as well, is how can we help drive jobs more at that beginning of the funnel with early stage companies? So if early stage companies have success and grow, they're going to need more heads, more bodies, more you know, jobs in that equation. And so that's something that I would feel really proud about as well as we move forward. But we have a three year, five year plan, of course and outcome based in order to accomplish that. And we, you know, I'm excited to share some of these different approaches, because we are using them internally as well alongside of these growth companies, and it's going to be a learning experience in in a complete way that we can, we can provide back, you know, feedback and live documentation as well.
Erin Geiger:Yeah, that's a beautiful thing when you can create something that then impacts the livelihoods of
Unknown:others, definitely, that is the goal. Yeah,
Erin Geiger:that's incredible. Okay, as you look back, you know, I love asking this question, because, like I said, we have some listeners that are, you know, beginning their journey. Some are, you know, further along. But I think for everyone, this helps, like, if you could give a solid piece of advice, you could even like picture yourself, you know, as when you were, when you were first starting out, but you know some leadership advice, especially to the women out there who continue to grow, continue to evolve. What? What do you think you would highlight
Unknown:advocate for yourself and the power of many, it is impactful. I would, you know, if I were to give advice to myself, oh gosh, 20 years ago, way back when I. Mean, I would say, don't necessarily try and go it alone, like if, if you have an idea, believe in yourself, but network, find other people, because it's, it's I've found it's very common that if you believe in yourself, and you believe in an idea and you want to follow through, in that there are others out there as well that can contribute an impact to to what you're trying to accomplish.
Erin Geiger:Yeah, that's and that's huge, having that sort of mindset. It's like other people want to help you succeed and believe in what you're doing, and so allow them to do that. Open that door.
Unknown:Yeah, absolutely. I mean, I think that's, that's the biggest, I don't want to say mistake, but the biggest thing I probably had to learn early on is that there are others out there that actually want to serve and help you, if you just allow them to.
Erin Geiger:Yeah, and throughout all of this, like, what? What is it that you do that helps you find inspiration? Helps you recharge. You know, is it meditation, working out, spending time with your kid, like what? What is it that kind of rejuvenates you?
Unknown:My kids inspire me each and every day, I have two kids, I have to they're both in high school, a daughter and a son, and they're competitive athletes, so I watch them and draw so many, so many different inspirations just watching what they go through. I have a daughter who is working on, being recruited for college, for d1, for swimming, and is a sprinter. And I'll give you one example of like, something that I think about that inspires me is She's a sprinter, and so she has, you know, a main event, 50 free, among others that she does. But in that 50 free you have to control everything that you can absolutely control and ignore the things you can't control. And watching her do that inspires me, like, for instance, she may go up against someone who's six feet tall and she's average height. She can't control her height, so that's something that you just have to learn to not control. But you can control getting off the blocks quickly, and control your turn and in that, you know, control how many times you take a breath. And so that is something that I looked at and said, You know what? In life or in a business, you have to focus on the things you can control, and you have to kind of ignore the things you can't. So whether that's like competition that you're looking at when you're a founder, you can't control what your competition is doing, and neither can my daughter, essentially, but she can control what she has to give and different levers, you know, I would say, in a given race like that. And so I think about that a lot, you know, launching this business like I look and I say, oh, there's someone else that's like, a little bit in her space, but they're different, and should I focus on them? And will they be competition, and do I need to be worried about them? And it's like, you know what? You can just leave them aside because you can't control what they're going to do. But we can be the best we can. We can drive forward our mission, and we can serve everybody in the equation of what we're trying to build. So inspiration from my kids, I would say,
Erin Geiger:Yeah, I love that. It's a It's true. It's like you're really just in control of how you navigate and how you respond honestly to things that come your way. Stephanie, this has been so great. Thank you for taking the time. I would love to know, where can people find you online if they want to connect?
Unknown:Yeah, so LinkedIn, I am more than happy to connect with anybody. Stephanie Quay on LinkedIn, also when we launch, which will be, I think after, I think, I think we'll you will have launched by the time this goes live, five experts.com and always can email us at growth at five experts.com
Erin Geiger:as well. Very cool. So we'll include all those links in the show notes. So thank you. Again, Stephanie, really appreciate the time and good luck on the launch. I'm so excited I have a front row seat. So excited about that.
Unknown:So excited. And thank you so much for the time as well. This was fun. Super
Erin Geiger:fun to catch up as well. Awesome. Bye.