34. Why Female Founders Thrive: Lessons from the Frontlines
EPISODE 34
Jess Schultz, the founder and CEO of Amplify Group, shares her unique journey from finance to entrepreneurship. She emphasizes the value of support and progressive networks for women in business.
Catch the Conversation
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As the founder and CEO of Amplify Group, Jess Schultz is a go-to market supercharger for B2B startups looking to achieve scalable goals. She loves to build companies, teams and pipelines; as well as connecting people to other people, resources, and solutions. She is on a mission to keep learning and growing everyday. Jess started her career in Capital Markets, then shifted to Saas Sales, then Venture Capital, and is now a proud founder and operator. She brings a unique perspective to her client engagements, having worked at large enterprises, and small businesses, as an investor and as a 'classically trained' salesperson.
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Julie: 0:04
Welcome to Figure Eight, where we feature inspiring stories of women entrepreneurs who have grown their businesses to seven and eight figures revenue. If you're in the mix of growing a bigger business, these stories are for you. Join us as we explore where the tough spots are, how to overcome them and how to prepare yourself for the next portion of the climb. I'm your host, Julie Ellis. I'm an author, entrepreneur and a growth and leadership coach who co-founded, grew and exited an eight-figure business. This led me to exploring why some women achieve great things, and that led to my book Big, Gorgeous Goals. Let's explore the systems, processes and people that help us grow our businesses to new heights. If you're interested in growing your business, this podcast will help. Now let's get going. Hello and welcome to this episode of Figure 8.
Julie: 1:06
Today I am chatting with Jess Schultz, and Jess is right now the founder and CEO of Amplify Group. But, like any good entrepreneur, she has a pretty eclectic story of the path she took to get there. She's a great team builder of people, of companies, of pipelines, and she started her career in capital markets and moved to SaaS sales and then venture capital, and now she herself is a founder and operator, and I think what she's doing is really exciting, so I'm very happy to welcome you today, Jess, Thanks for joining me. Thank you for having me. I appreciate it. Yeah, thanks for joining me. Thank you for having me. I appreciate it. Yeah, no problem. No problem, I think your path is. I always love the eclectic path because I feel like mine has been, you know, kind of in different spaces than you, but that same level of you know you pivot and go somewhere else and just keep moving up in your career. What can you tell me about how you got started and how you ended where you are?
Jess: 2:09
Sure, I started as a finance major in college because I was good at math and my parents were CPAs, so that just seemed like a natural thing to do. I didn't. We didn't get much career counseling. I don't know if that's changed. I hope it has. Um, so I, after I graduated, I went into finance at a bank. Um, just cause I didn't know, honestly, I just wasn't aware of all the opportunities really within finance, so bank was just kind of a natural thing. Um, so I worked. Uh, I was fortunate enough to get my first job at Deutsche Bank in London, which is an amazing experience. And then after that I worked for Merrill Lynch for many years in both Chicago and New York.
Jess: 2:52
I was always in the capital market sector of the bank, so more of like the institutional side, not the retail side, enjoyed it, learned a ton, but candidly, it was just not lighting me up maybe is one way to say it Very high stress, very, very misogynistic, very highly regulated, and so I was looking for something different. But I had, almost at that point, like eight or nine years of experience in that sector. So my thought was you know, everything's moving, electronic and and software and and SAS was like like, almost like a new term at that point. So I went and worked at a trading software company where I sold, I was selling software to the same cast of characters, same that I worked with at the bank, but it was a software company versus a bank. So it was a very different corporate culture, which was nice. Learned a ton about technology there because trading software is highly technical. But then I always kind of had my eye on getting out of the trading world altogether. So once I had some experience in software sales, then I transitioned to a company called Trinet and that was a pretty big pivot because it was selling HR services and software to startups and small businesses. So really different than anything I'd done up to that point.
Jess: 4:20
But I was excited about the opportunity One. It's just like a need to have product, which as a salesperson I love selling something that you need to have versus a nice to have, and I really believed in the value, prop and the value that they were providing the startups and SMBs. And then it was also an opportunity to work with venture capital and private equity. So they had Trinet, had had a lot of success with that as a go-to-market strategy on the coasts and they wanted someone to build that out in the Midwest. So I joined and got exposure to that world which I fell in love with.
Jess: 4:57
I just loved the optimism and the ambition that startups have at those early stages and like working with those investors was really fun. So I did that for about three years and then one of the VCs that I worked with quite frequently was like oh, we're actually looking to expand our team. Would you want to come work here? And that wasn't a career path I'd ever envisioned honestly for myself. But I was like you know, what do you want with me? I'm like a derivatives girl turned salesperson. I don't, you know, I don't have the traditional like iBanking or M&A background. And they were like no, actually like we love your background.
Jess: 5:40
We think venture capital is 90% sales in many ways, and once I joined I agreed with them it is a lot of sales motions, similar sales motions so joined the firm, worked there for about a year. It was a great experience, but I just I missed being more, I guess, more of an operator. Like when you're an investor, there's only so much influence and involvement that you're going to have, especially as a minority investor where you don't have a huge ownership stake, and so I really missed being intimately involved with businesses, and I realized in my time there that a lot of the founders that I was working with in our portfolio had the same go-to-market challenges and I didn't feel like there was many really great solutions for them in the market, and so I created Amplify three years ago to basically serve those needs that I didn't feel like were being met. So that's what I do now.
Julie: 6:40
Yeah, and it's such a journey from big, big corporate to working with entrepreneurs, especially in the stage you're working with them at where they're in that go to market, you know, up to series, A kind of kind of phase right.
Jess: 6:56
Yep, yeah, it's a little volatile and a little crazy, but I like it.
Julie: 7:03
Yeah, I think it's interesting too because I mean, obviously you kind of grew up your career in pretty male dominated industries, um, and do you see diversity now with the kinds of entrepreneurs that you're working with, are you able to create sort of that, you know, kind of environment that you want?
Jess: 7:23
Yeah, I mean, that's one nice thing, I guess, about owning your own business is you get to write the rules to some degree. And another woman that I met with like early on in starting my company, I met with several other people that do similar work to me, just to try to get peer to peer feedback on you know how to structure things, et cetera. But something she said to me I'll never forget she was like I have a no asshole policy. If I don't work with assholes, if they're an asshole, they got to go. And I was like I'm going to institute that right away. So, similarly, I'm thankful that I haven't had to quote, unquote, fire many clients. I've been grateful to work with a lot of really wonderful people, men and women but I do have a no asshole policy and thankfully I do get to work. I feel like every founder that I do support is very progressive and very respectful, and I've been grateful to work with a lot of female founders. It's been awesome.
Julie: 8:21
Well, that's good. So when a founder, what would? When a founder comes to you, um, just tell me kind of what that path and journey looks like in terms of how you work together and what you do for them.
Jess: 8:34
Yeah. So, um, nine times out of 10, I start them out with what I call a go-to-market audit. Um, and, and I'm a firm believer that when you're having like growth challenges or you have growth goals, it's not there's no silver bullet, there's no like, oh, it's just this one thing. If we do this one thing, everything cashes. It's gonna rain cash. Usually it's a more complex Rubik's cube to put together to really like take the company to the next level.
Jess: 9:05
So I and I am saying I have is, you know, I hope a doctor wouldn't give you a prescription without an exam.
Jess: 9:12
I similarly don't want to come in and prescribe things until I really, you know, have an educated understanding of where your business is today, where you want to go.
Jess: 9:20
So we spent 30 days doing that go-to-market audit, which is a deep dive of like what is their product, who's their target customer, who are their customers today, how did they get them? I do a lot of competitive analysis on like other competitors they have in the space, get more color. So it's really like a holistic process that I go through to come up with okay, based on everything I learned and observed and what I know you told me about your goals. Here's what I think we need to do in the next 30, 60, 90 days to get you where you want to go, and then we move into like execution mode. So the audit itself is like a 30-day process and then the execution really varies business to business. But most businesses work with me six to 12 months to get them to the point of maturity that they don't need me around like full time anymore. Well, I'm not full time, but they don't need me as much anymore.
Julie: 10:19
Yeah, or they've been able to, you know, get to a point of traction where they can hire people in-house to do those kinds of jobs and kind of it's, you know, moving along that scale of, or that continuum of, scaling up. Yes, correct, kim, because well, as you said earlier, there are not a lot of people slash, nobody really kind of doing exactly where you know where you're playing in the space, nobody's really doing it.
Jess: 10:53
There are a couple other people. No one else does it quite the same way I do. I mean and I guess that's true of everyone, right? I think what you mostly see out there is like there are people that do. They might call themselves a fractional CRO, but I think they're really more like a fractional VP of sales, meaning they come in and act as like a sales coach and mentor and just help with the sales process. And then there's fractional CMOs or fractional marketing folks that will help you with content or digital marketing activities. I'm a little unique in that I do both like the sales coach and strategy plus the marketing, just because I feel like it's so important to do both at that early stage, and usually my target customer can't afford to have two of me, so yeah, Well, I think that's the real, you know, as you hit the seven figures.
Julie: 11:46
It's the real problem of you need all the people, you need the whole team, but you cannot afford the whole team. Yeah, yeah. And so how do you like it feels like it makes sense that those two come together and, you know, maybe when the company's bigger they break back out, but it feels like it makes a lot of sense for you to think about them in a holistic way. Yep, yeah.
Jess: 12:29
Yeah, and so now, as much as you know it always is.
Jess: 12:36
But I think you know someone once called it to me like life tuition, and I think it's kind of like entrepreneur tuition, like you have to pay your tuition, you're going to make, you're going to do some things right, you're going to do some things wrong, and you just you live, you learn, you pivot. I think for me, scaling what I do has been very challenging, like scaling myself, because exactly what you just mentioned, like in a, I'm a bootstrapped business. So in a perfect world, if I were to, you know, if I had the money, I would hire a copywriter and a designer and a SDR, right, I would have like a whole team of people that have like functional disciplines. But that's not really financially feasible to bite off like that payroll all at once. And then so for me I tried to hire people that were more even though I kind of hate the term like Swiss army knives, like people that had more than one skill set that could kind of like bob and weave into client engagements like I do. But it's really hard to find those people, to be honest, and it's not that they don't exist, but sometimes they exist and they have salary demands that would make it challenging for the margins and the math to just make sense. So I think, like just staffing and figuring out how to staff and scale what I do into an agency I haven't figured that out. So I did try and I scaled back down to being a solopreneur in 2024, just for my own sanity and bank account. But I do still personally believe that there's way more demand for what I'm doing than there is supply and I think it's such a win-win for me or any other consultant and for the customer, especially for the startup market.
Jess: 14:31
You know they don't need me or someone like me full time. And for me, I love, like the variety of working on multiple businesses at the same time. I think a lot of people that maybe have a similar personality to me would, too. You get kind of bored if you're just work, if you're just selling the same thing for three years straight, but there's a lot of fun and in getting to switch and work on different businesses and so like it's really rewarding and it's great money, like I mean, candidly, I do make better money doing what I do now than I did like full time at an organization. So I think like anyway, it's a really good win, win for both sides.
Jess: 15:12
So I would like to find ways to help more people become me or like do what I do, so to speak. So I'm trying to figure out how I do that, and my first attempt this year it's brand new is to start off offering coaching, like one-on-one coaching, for people that either already are a fractional go-to-market leader or want to become a fractional go-to-market leader, and I'm hoping, through those like one-on-one engagements, I'll really intimately learn like what people need to get to up, to level up themselves and to really like build their own business. So I hope to be, and then I hope to somehow maybe turn that into like a digital course or a community. I don't, I don't know what that becomes as a phase two, but something that is more, I guess, approachable to the masses.
Jess: 16:05
Um, in particular, with the employment environment that we're seeing, there's a lot of really good people out there that have lost their jobs at big companies, and so I think, like if I can activate more of them to be to like fill a role like this. So, anyway, that's kind of a long-winded answer, but that's I'm. I'm trying to solve the problem of like how do I scale myself and and how do we scale people to do what I'm doing for more companies, because I think it's really a need.
Julie: 16:37
Yeah, and I would agree with that. Like finding the right product, market fit, how you go to market what's happening all around that time as you sort of start to get sales, build sales and get feedback from those early customers so that you can get to those you know out of your seed round and up to series A. Like all of that, happening relatively quickly is important and having a structured process, I think, probably helps entrepreneurs a lot.
Jess: 17:07
A hundred percent yeah.
Julie: 17:09
Yeah, Just because I mean they're trying to do everything right, they're trying to, and, and the CEO is always the first salesperson. I mean, that's the, you know, they're trying to do everything right, they're trying to, and the CEO is always the first salesperson. I mean, that's the, you know, they're the one who had the dream, the vision and imagined it, and so they are the best salesperson for a period of time. But often, you know, no one has all the skills they need to do all the roles that they are currently trying to fill.
Jess: 17:36
Yep, and I think there's a lot of noise out there, candidly, like there's a lot of go-to-market advice, and so I think for founders sometimes too, it's like hard to know what to listen to, like how to like break through the noise and and I think sometimes they get taken advantage of as well Like companies come in and try to sell them like 10K a month PR retainers, and it's like that's just totally unnecessary sometimes for, like the stage of their company or whatever. So I think I hope to educate more people and that's what I try to do through my content, et cetera is like here's what you really need to know for this stage, here's what really matters and here's why, and here's what you really need to know for this stage. Like here's what really matters and here's why and here's what you should be spending on it, and anything else is just like predatory, you know like and not necessary, and like it just doesn't have to be as complicated as some people like to make it seem.
Julie: 18:31
Yeah Well, and it's so easy to see an entrepreneur who is is so blessed with advisors, but they have so much advice coming at them that they don't know actually what's right for them, what to believe, what to follow and take up and what to shed. And you know, I do a lot of talking to people about, like, who are the like three or four cornerstone advisors that you are really pulling in and taking, keeping close, you know, because you can't, like it just becomes so noisy and you just you can see the freezing up that happens right, and the inability to move forward.
Jess: 19:13
The analysis paralysis yes.
Julie: 19:18
Yeah, and especially yeah, you. You know, you see it at a table and it's like conflicting advice coming from every single person and you're like how do you decide? How do you cause it is hard to decide and there there probably are multiple paths. How do you know which is the best one? So, and it's where your background, I think, brings an interesting like this sort of rigorousness and discipline that you can bring from, like, your capital markets background and that sort of thing, and then the sales piece and how you can bring those together to help them really figure out how they're going to get off the ground and start to fly.
Jess: 19:54
Yep, no, completely agreed. I'm very process oriented and I think that's a requirement, like another little saying I say often, which is like clarity is how you begin, but consistency is how you win, and so it's like about creating the right processes that are repeatable and scalable, and then it's just running that play over and over and over again and it's, I think, too many times they startups, well, they don't know where to begin because there's a lot of analysis, paralysis, or then they start and stop things a lot and there's not a lot of consistency or commitment, and so then they don't ever really see anything work and it's like, well, yeah, because that nothing will work after one week or one month. You know, in general, you got to give it a little more time.
Julie: 20:38
And that can be so hard as an entrepreneur, because you started out in the beginning where you were like decision, decision, decision, go here, go here, go here, oh, let's pivot, oh, let's pivot. And it didn't matter. You were getting the little traction in the small state you were in and make crossing that bridge right Of like, oh, I can't just decide to make to turn right tomorrow. I have to, you know, really think about it and make sure it's the right thing. And how long is it going to take if we do turn right? And you know like every decision has that many more implications as you get a team around you and you start getting the traction Totally. Sometimes that feels boring to people too, right?
Jess: 21:25
Yeah, and I think the thing they at least from what I've observed I think the reason why they pivot a lot is because they don't know how long something should take, just in general, and they don't know what good looks like, so they don't really know. Like you know simple things right, like is this open rate on my email good? I don't know, so I don't know. Does the email suck? Is it my subject line? Like they don't. So I try.
Jess: 21:46
That's where I try to educate. Like I focus a lot on that is like educating. Like, okay, if, for example, you want to pursue SEO as a strategy that's a long-term strategy we have to have at minimum, a four to six month commitment and this is how we're going to know it's working. These are the metrics we're going to see as leading indicators that it makes sense to continue to invest and this is how we're going to even. These are the metrics we're going to look forward to know if it's even worth investing in for your business. And so, like I think it's just educating them on. These are the. There is some data that exists and that we can use to help them feel more confident about making the commitment and sticking to the commitment.
Julie: 22:28
Yeah, and then in the you know, and then how do they build their own data to track their progress once they get started?
Jess: 22:34
Yeah, exactly.
Julie: 22:36
Yeah, yeah, because that's the. It is the piece of like. In a world where we have endless data, it's amazing how hard it is to find the right pieces and the right information to kind of hone in, that are useful instead of like just part of a big ocean.
Jess: 22:57
Yep, no, it's so true. We're like inundated with too much data sometimes.
Julie: 23:01
Yeah, yeah. And so, therefore, picking out the parts that we need feels overwhelming. Yeah, yeah, yeah. And I know I often think about like we talked about this in our own business. We had an unlimited amount of data at our hands and we, you know, would often sort of like lament that we weren't using it all, but. But I sort of have that feeling of like but but if if we're pulling it for the sake of you know, like it's garbage in and garbage out, like yes, we have it, we need to use these pieces. We need to figure out what pieces of us, of it, are most useful for us at any given point in time.
Jess: 23:42
Totally agree. Um, and I had something you'll probably resonate with, but my fractional CFO cause. I hired one of those Cause. I was like, even though I know finance, I've never run a business finance and so I need to learn that skill set. And he said something so important to me.
Jess: 23:59
I remember I was trying to track something related to client margins and he's like Okay, Jessica, he's like I'm going to ask you a question that I want you to ask yourself whenever you're having one of these moments. And I was like, all right. And he's like Are you going to do anything once you have that information? And I was like, all right. And he's like are you going to do anything once you have that information? And I was like, no, like, like, for that moment, anyway, you know, he's like are you actually going to do anything different? And at least at that point in my business, even if I had the data I was seeking, I couldn't. There wasn't much I could do with my current team size and whatever, like. So it was such a good realization moment where I was like am I going to do anything if I have it? No, okay, then I don't really need it Right.
Julie: 24:41
And then you can sort of think, okay, and if I ever do need it, I know we can get it. And then so right now, cause it's also that like you could have them pull it or or you know, like sort through it or whatever would need to happen to give you something served up to you that was useful, but it's a waste of money and time to have them do it for the sake of throwing it in the garbage.
Jess: 25:05
Essentially, yeah, so sometimes I think we all get fixated on like I need to know this answer, but it's like, do I?
Julie: 25:12
What do I really need to know? Yeah, yeah, and I think that's where, like having that process of like how you go in, you gather information and then you know you've got to at some point, lift back up, you've got to go to work, but you've got to have a process where you lift back up and like do the check, because things don't stay the same.
Jess: 25:33
Agreed. Yeah, especially in the sales and marketing world, I feel like, well, at least that's the world I live in, so I know. I'm sure it's probably true for a lot of other disciplines too, though, but things are changing all the time.
Julie: 25:47
Yeah, they really are. And yeah, you think of, I mean, and now with AI and all of the other business tools that are, you know, that's revolutionizing a lot of parts of what we all do revolutionizing a lot of parts of what we all do.
Jess: 26:04
Yep, I'm a big like I mean. Now you brought up AI but I'm a big believer, though. You should only use AI, in my opinion, um, to automate or to do something If you already know how to do it, like like you actually know how to do it. And I feel like the thing that people fall victim to is like they don't know how to write a good cold email period, and then they just use AI to write a cold email, and I'm like, well, if you don't even know what good looks like, you can't even check AI. So then what? So that's, I don't know. That's my own rule of thumb with AI is.
Julie: 26:32
I'm like I only use it if it's something that I actually know how to do, because then I can at least validate that the results are what I would expect, or yeah, I think that's a really great point about it, because it's true that, yeah, it's again, it's the if you don't know what garbage looks like, you can't determine if it's going to help you. Like, even though you feel like it saved you a lot of time, it still might not be worth it, right? So I think it's a tool and, yes, it's inevitable to use it, but I think it's a really great point about being able to assess what you get from it and whether it's what you really want.
Jess: 27:16
Right, yeah, yeah. So some of the young people, I think, think might not get as far as they think, because they're just going to use AI to do stuff they don't really know.
Julie: 27:24
But yeah, and so who is it that you want to work with? What's the profile? I mean, we talked about kind of size, of where that business is and where they're headed, but what kinds of businesses? What are the verticals that you look at when you think about working with some of these entrepreneurs?
Jess: 27:47
Yeah, for me, like a hard requirement is that it's B2B, like a B2B go to market motion. I just don't know enough about consumer, even though I'm fascinated by it, but that's a totally different growth strategy. So it has to be B2B, has to be software, which is just my own personal thing. There's a lot of challenges with scaling a services business, some of which I alluded to earlier on this call. So I just anyway, that's just not a challenge I choose to tackle. So B2B software and then vertically.
Jess: 28:18
I worked in capital markets for a long time so I tend to attract a lot of fintech clients just because I have that core subject matter expertise. And then I also sold benefits in HR, so I know a decent amount about health care and insurance and benefits. So I've attracted a lot of clients in that space. But I've certainly worked with a handful of B2B businesses within other verticals too. I would say, like, maybe the other requirement for me is that it's a more complex sale or like a higher ticket item. So if it's like a $99 a month, you sign up with your credit card, I'm probably not the best person, or I'm not the best person like that kind of growth motion, like a product led growth or like that. More transactional sale is not my expertise or my passion. I'm more of like the 30k annual contract value to like a million dollars Like how do we close this really complex sale that has multiple stakeholders involved? So maybe that's more of a requirement than the vertical specific.
Julie: 29:28
Well, and that makes sense, you know, going back to what you said earlier about how you kind of your process is that you really pull everything apart and look at what they're doing and look at where, how and where the best opportunities are for them to chase, how to go after them, and then you pull it back together and that makes a lot of sense when you think of that size of a, of a sale.
Jess: 29:49
Yeah, cause the more transactional stuff is a lot more like marketing automation and there's nothing wrong with it, like that's great. It's just a little, I don't know.
Julie: 29:59
They're all hard in their own way, but it's different, it's the truth, all businesses are hard in their own way and I think, like generally speaking, in the entrepreneur community, we are all we feel all very driven there. You're talking about very driven, successful people, and so it is like hard to understand what you don't know or that you know. That, like always feeling like you're on a learning curve can feel really hard, and it's the same. I think it's so interesting because when you work with other entrepreneurs, you see it in them, but it's also true for yourself.
Jess: 30:32
oh, 100% and uh, another woman I know. She says it's hard to see the label inside the bottle, and I'm sure she got that from somewhere. But I love that saying and because it's true like it's easier for me to diagnose problems in someone else's business than it is even in my own, so like I've hired my own host of advisors and consultants because I'm like, come give me some objectivity. Like sometimes it's hard for me to see my own label.
Julie: 30:59
It's a great point and I think it's hard for me to see my own label. It's a great point and I think it's easy for that to build accountability for you with the people that you bring in to help you and that then you know you can go on your own path of looking at what you need to do to grow and scale Well. Thank you so much for joining me today. I really appreciate it. It was a great conversation with you and I'm so glad we got introduced. Thank you for having me. I really appreciate it. It was a great conversation with you and I'm so glad we got introduced. Thank you for having me. I really appreciate it. I hope you enjoyed today's episode. Please remember to hit subscribe on your favorite podcast platform so you won't miss any episodes.
Julie: 31:32
Figure 8 isn't just a podcast. It's a way of seeing the big, gorgeous goals of women entrepreneurs coming to life. If you're interested in learning more, you can find my book Big Gorgeous Goals on Amazon, anywhere you might live. For more about my growth and leadership training programs, visit www. julieellis. ca to see how we might work together. Read my blog or sign up to get your free diagnostic. Are you ready for growth? Once again, that's www. julieellis. ca. When we work together, we all win. See you again soon for another episode of Figure 8 .