Sara Leoni, CEO of Ziplines Education Spills All on Securing Series A Funding

Our philosophy is based on providing a very hands-on, very practical, very experiential learning experience to people who are looking to upskill or reskill or really just learn something new.

Sara Leoni

This week on the On Work and Revolution podcast Sara Leoni, CEO of Ziplines Education, is in the guest chair – and she shares invaluable insights into both the challenges and the FUN solving challenges in the education technology sector. And when your mission is as massive as to revolutionize learning and empower students globally, you need to find joy along the way.

Three key points emerge in this conversation:

  1. Innovation in the EdTech Sector Today: we dig into bridging the gap between traditional education and the demands of the modern workforce.
  2. Building a Workplace Culture based on Transparency: The importance of fostering a transparent, collaborative, and empowering workplace culture is emphasized, where individuals can thrive and contribute to the organization’s success.
  3. Securing Series A Funding with Grit: We spend a lot of time touching upon the challenges and strategies of raising capital in EdTech, the significance of building investor relationships, and the vision for scaling the business in the future.

Give this conversation a listen, and don’t hesitate to Contact Us if you have any questions, comments, or feedback. 

About our guest, Sara Lioni:

For the past 20 years, Sara has honed her expertise in management, marketing, operations, and building innovative online brands for major corporations, as well as startups. In 2017, she joined GreenFig, now Ziplines Education, a market-driven education company that provides career-driven professionals with the job-ready skills, technical training, and experience needed for today’s digital-first job market. She is an in demand speaker at industry-leading events and conferences, such as the UPCEA Annual Conference, the ASU+GSV Summit, which is an annual collaboration between Arizona State University and Global Silicon Valley, and Dreamforce, Salesforce’s annual international event.

Her philosophy is this: if a team is tenacious in their pursuit of understanding the customer — you can make a profound impact on their world. 

Open for Full Episode Transcript

[00:00:00] Debbie Goodman: Welcome to On Work and Revolution, where we talk about what’s shaking up in the world of work and ed tech. I’m your host, Debbie Goodman. I’m CEO of Jack Hammer Global, the global group of executive search and leadership coaching companies. I’m also an advisor to venture backed ed tech founders. And for those of you in ed tech who are hiring, we have launched a fractional leaders offering.

I’ll put a link into the show notes about that. My main mission with all of my work is to help companies and leaders to create amazing workplaces where people and ideas flourish. So today I’m really excited to have Sara Leoni as my guest. Sara is CEO and founder of Ziplines Education, which partners with universities to deliver industry focused certificate courses that prepare students for today’s digital first workforce.

In other words, They’re helping to close the skills gap between higher education and the actual needs of the working world. Ziplines Education has gone through some very big advances recently. So firstly, a rebrand, it was previously called Green Fig. And then very impressively, they announced a Series A funding round about, about a month or so ago.

We’ll get into all of this in a bit. This is not Sara’s first rodeo. Prior to launching Ziplines, she was CEO of Rafter, a $50 million course material technology management company that served hundreds of colleges nationwide. She’s also a highly respected thought leader, very in demand speaker at industry events like ASU GSV, Dreamforce, which is Salesforce’s annual global event and the UPC EA annual conference, which is the premier event in the continuing education space. And today we’re going to chat to Sara about her journey with Ziplines Education and what it takes to attract capital in the ed tech sector right now. Welcome Sara.

[00:02:03] Sara Leoni: Thank you. I’m so happy to be here. Thanks for having me.

[00:02:06] Debbie Goodman: Uh, it was so great to see you at the ASU GSV summit. I was impressed we bumped into each other like three times, which is pretty impressive considering there’s 7, 000 people.

[00:02:15] Sara Leoni: I was going to say, yeah, you and the other 7, 000 of our best friends that were there floating around. 

[00:02:21] Debbie Goodman: Yeah. And caught each other’s viruses. So exactly. All right, let’s get into it. So Ziplines Education what is its core offering? Tell listeners a bit more about the company and its mission. 

[00:02:33] Sara Leoni: Yeah, of course. So, you know, at our core, we are really helping aspiring professionals as you mentioned, acquire the in demand skillsets, really practical skillsets and hands on experiences so that they can build a career in a discipline that they love, something that they can really thrive in and something that provides them with the opportunity to really have social mobility, right. To be able to move things forward and enjoy a long and fruitful career. So, you know, at the premise, as fast as technology is changing, Skills are evolving, right? We, we see that today with, uh, generative AI and the news around how AI is disrupting the workforce and what that’s going to look like.

And so our goal is to create a very authentic approachable learning experiences. where people can come in, they can develop the skills in a really safe environment. They can put those skills to use in hands on exercises. And at the end, as you mentioned, we are partnering with universities, which play a really big role in our value proposition of ensuring that our learners, so, you know, average age is 35 years old.

I think a lot of people, when they hear university partners assume we’re working with, you know, college graduates these are adult learners that have been in the workforce and recognize they either need to refresh their skills or they need to develop new skills to continue to move forward. And so having that employer ready credential, right? Having the credential from a brand like a higher education institution that’s so well known in the universe is really important for those employers. Just understanding the value of the skills and the credentials that these, uh, that these learners are, are building as part of this process.

[00:04:21] Debbie Goodman: Well, I mean, that sounds really hopeful and very exciting, particularly for people in the workforce who are starting. I mean, I hear a lot of fear with people who are going, I don’t know when, whether I’m going to have a job in a year or two years or five years, or what part of my job will still be human and what part of it I’m going to have to, you know, hand over to an AI. And more importantly, what additional skills can I use to future proof my career and my livelihood? 

[00:04:47] Sara Leoni: Absolutely. Absolutely. 

[00:04:49] Debbie Goodman: Okay. So, why the rebrand and how did that come about? And then how did you feel about that? Because I, just some context to that, Jack Hammer is a brand had there been various iterations along the way where I’ve thought maybe I should really change that, but it’s a, maybe a little bit of an aggressive name for a headhunting company, but I feel emotionally attached to it and I don’t know if I ever will. So I’m keen to hear about the, the why and how you felt about that. 

[00:05:16] Sara Leoni: Yeah, you know, I think this is where I didn’t have a strong emotional attachment to GreenFig. I inherited that brand as part of joining the, the company as it existed a number of years ago. And you know, it, it when you step back and think about what, what did it stand for?

Green was really meant to be, I’m new at something. I’m coming into this without a lot of experience. And fig is the tree of knowledge in certain cultures. And so while it, while it established a good foundation, it didn’t really, uh, provide the context around how we think about learning, how we think about, you know, the, The continuous impact learning is going to have in terms of our careers as we move forward.

And so, you know, Ziplines Education, when we think about what, you know, in its, in its brand essence, the idea is that as we look at our careers, especially because they’re going to evolve, right, we’re not going to have one career. I think some, Some reports tell us we’re going to have 10 to 12 careers, right?

We need to be able to have perspective. And so how do we, how do we really look up and look out and then set goals for ourselves and have a very active, and I think that’s the piece where we differentiate from a lot of folks in the market is our learning is very active. There’s nothing passive about it.

And so this idea of continuous. I set a goal. I accomplished that goal. I think the other thing I’ll share is, you know, some people ask what was the origin of Ziplines and it really, it came from a personal experience that I had zip lining years ago with my team in the Santa Cruz mountains. And I remember it being uh, terrifying, exhilarating. I remember feeling safe, even though I was terrified, it was safe. And I felt supported the entire time. And every time I went from one tree to the next tree, I felt like I had accomplished something monumental. And that’s exactly what learning is like, especially for adult learners.

As we think about it’s incredibly intimidating to put yourself out there and to learn these new skills. And so for me, it became, it really hit home and then gave us a very strong brand foundation to build on as we think about where we want to take both the product and the vision of the organization.

Debbie Goodman: Oh, well, I really love that. I’m thinking back to the first time I did a big zip lines.  All right. Let’s discuss the really big deal about your recent capital raise. What was that experience like? 

Sara Leoni: Yeah. I mean, the simplest way to, uh, to communicate it, it was brutal. Fundraising is. But some people find fundraising a fun process. 

[00:08:00] Debbie Goodman: No, no. Who are those people? It is rare.

[00:08:03] Sara Leoni: It is rare. But you, especially when you’re in a very early stage organization where it’s, You know, at the time I was wearing a VP of finance hat. I was wearing a head of product hat, was wearing a head of sales hat. I was wearing a, you know, on and on marketing. And you, you know, in order to successfully fundraise a, you have to pull yourself out of a lot of those things and really put a lot of your attention 70, 80, 90 percent of your attention towards the fundraising process. And, you know, it is again, at an early stage, it’s like, you’re on this roller coaster, right? The highs are amazing and the lows are horrendous. And then in between that process, you basically have to hide all of those emotions that are happening in the background and you have to put your best foot forward, right?

You have to really showcase that everything is amazing. And we’re building this incredible vision, even though, you know, you’re having these insane ups and downs. And so it’s just, it’s really a very emotionally taxing experience. And, we all know that the vast majority of investors that most people talk to are going to say no.

[00:09:17] Debbie Goodman: Exactly 

[00:09:18] Sara Leoni: And in many cases, they’re going to tell you why they’re saying no. And so you’ve, you’ve worked really hard to build up a strategy and, uh, you know, set of specific achievements that you want to accomplish. And then you get all this feedback that it’s wrong and it’s really disheartening or yeah, it’s not what they want. And it’s really, really disheartening.

So, every time you get feedback, it’s really important you have to not take it personally, right, you can’t let it get you down, but it’s also a learning moment. And you know, some people will, they’ll be in the fundraising process and they’ll say, well, they don’t know what they’re talking about or, you know, they just don’t understand my business. And I’m like, that’s actually really good feedback, right? If they don’t understand, then either there’s something about the articulation of our business or our value proposition or the vision that I’m not, you know, putting out there with the right words or with the right intention. And so even though I may disagree, I always take it with, you know, this is something that I need to learn from and make sure I’m building into my thought process or my frequently asked questions, you know, that I’m going to answer on the back end and be ready to go to if I need to but it’s just generally gruelling. 

[00:10:34] Debbie Goodman: Yeah. I mean, you’ve got to hear, be prepared to hear a lot more no’s than yeses. I mean, that’s, if you think about the ratio of pitches to actual acceptances or agreements or, or letters of intention, I mean, it’s a, it’s a, it’s many, many pitches that you’re going to make and very few that you’re going to conclude. So I think that just an acceptance that more no’s than yesses and just being okay with that, but more importantly, also to refine the pitch along the way, because I agree with you, we get very used to our own language and our own terminology and our own way of explaining what we do and we think that everybody should automatically understand that. And then, you know, hearing feedback that no, we don’t get it is a good opportunity to refine what other learnings? Cause you know, we have a number of founders that listen to this podcast and many of them are going like, what the heck, how many times do I have to do this? So what else would you suggest? 

[00:11:27] Sara Leoni: Yeah. I mean, I think I definitely have different suggestions, based on where folks are at in the process. And I will say I spend a lot of time with more female founders than male founders, because I think that there are general characteristics that we bring into those conversations at times that we just need to focus on and work on specifically, you know, when I think about what investors are looking for, right? So this, this to me, I put my marketing hat on and I think who’s the persona. What’s important to that persona. And at the end of the day, what an investor is looking for is, you know, they talk about 10 X returns and I, I put everything into sports analogies just because of my background. When I think about what an investor is looking for, it’s that grand slam. If you’ve ever seen the movie from The Natural, which is a very good movie, it’s a little bit dated at this point, but he hits this grand slam and it knocks out all the lights and you know, they go busting. And I think in a lot of cases we think to ourselves, well, uh, you know, uh, a standup double or triple that brings in some runs, RBIs, right. Something that puts us ahead of the game is pretty incredible when you think about the fact that 70 to 80 percent of companies are striking out, right? But at the end of the day, it’s not that double or triple that investors are looking at. It’s how do we really help achieve the outcome that is potentially going to make our You know, make the, the investment, you know, our, our portfolio that we have.

And so I try to put that hat on because, you know, I think in terms of both roadmap and flexion points and what’s doable, right. What’s possible. And I think in many cases, what we end up articulating as part of these conversations is, you know, almost too much of what’s in front of us.

And, and I will say I articulate too much of what’s in front of me versus really thinking about that attainability versus what’s the possibility. You know, at the end of the day, investors are really looking at what is the possibility? How big can this be? What is your vision? And it’s really easy to get tied down into the day to day, like you’re so excited just about the traction that you’re having in the market.

[00:13:48] Debbie Goodman: Yeah. I mean, that’s very similar to some advice that I was giving recently is that an investor will invest if they believe that there is something really big up ahead, particularly in the venture world. And so even if you don’t necessarily know how you’re going to get there, even if you’re not sure how you’re going to attain it, how the hell are you going to get there, but you believe that the possibility exists. That’s what people buy into. So, and perhaps to have a balance of both, like this is a possibility. This is where we are now. This is what we can see in front of us, but eye on the prize. So, and I think sometimes particularly female founders that I advise want to be more realistic than overshoot for some reason or another.

They don’t want to put something that’s so far out there that it feels unrealistic and unattainable. And I think that, I don’t know whether that is a agenda thing going on here, Sara, what, what would you say about that? 

[00:14:39] Sara Leoni: I mean, I definitely think it is, I mean, having spoken with you know, different CEOs, different genders, different advisors, different genders. I do think it’s the, we do focus on what can I attain, right? What do I, what do I have confidence that I can personally build over some timeframe versus what’s the possibility, right? And really, really painting that picture for what that possibility is. And I will say I’m more of an operator versus, you know, that visionary thinking long, long term. And so I really have to force myself because I want to talk about all of the great metrics in the business and how well we’re doing, and they care about that, but they really care about where’s it going and you, and you have to force yourself to, to flip that switch. I think one thing, one recommendation that I would absolutely make, and I did this a couple months before I officially raised our series A. I kept pitching to people and getting feedback and recognizing, okay, well, their feedback’s helpful, but it’s so all over the place.

Everybody has different feedback to how you pitch. And I asked a girlfriend of mine who had just recently raised a series A. I said, can you pitch to me like pitch to me how you would pitch to an investor? And it completely opened my eyes up to, Oh my, it’s not, you know, there’s the slides and we spend so much time on our slide deck and perfecting every bullet point.

And when I saw her pitch, like, yes, the slide deck was important. The most important thing was how she showed up. Right. What the confidence, how she positioned the possibility and, and didn’t focus on well, what were the roadblocks that might be in the way it was like, there are no roadblocks, right. We’re going to, we’re going to accomplish this and we have the team to do it. And there was just so much inherent confidence in it. And that in my head just flipped my switch in terms of, okay, that’s what I need to do. Right. That’s how I need to show up. 

[00:16:43] Debbie Goodman: What were you, what do you think you were not doing as well?

[00:16:49] Sara Leoni: Yeah, I definitely think again, it’s the possibility. Painting the story of the possibility and mine was, look, we’re building this incredible business and I wasn’t as willing to put myself out there in terms of, okay, I’m going to paint this picture for you. But I don’t know for sure if I can achieve that. I wanted to paint the picture of what I absolutely could achieve. You know, what I knew I had like 98 percent confidence that I could achieve. And that is not what investors want to see. 

[00:17:23] Debbie Goodman: Yeah, that is such a brilliant point here. And so I attended a couple of the pitch sessions at ASU GSV. Once again, just to get a sense of what is the differentiator, but with a founder, an early-stage founder, who’s nailing it and others who’ve got an equally good concept. Equally bankable, but just not. And it is absolutely about the demeanour, about the way in which the confidence about the self-belief, yes, it’s a polished performance, but it’s a person ability.

And it’s just that steadfast eye on the future. And so, I think that founders, particularly in technology, particularly the, those who are in love with the product as well, haven’t spent as much time working on their really performance. And so that’s such a great idea to get somebody else who’s, who’s just secured funding to pitch to you. I’m going to make those recommendations too, but okay. All right. So let’s just bring it back to female founders because you have had some hard lessons along the way. Certainly I have my volumes that I could trot out too, but what would you be able to, what you said in a previous call, you’ve kind of learned what works and what doesn’t as a female founder. Share a couple more of your pearls of wisdom. 

[00:18:44] Sara Leoni: Boy, I was going to say, I probably know more about what doesn’t work than what works, you know, at least on the investing side. You know, I mean, I think I have built a very strong relationship of respect with our investors, you know, they’ve had an opportunity to see how I grow my team, how I build my team, how I manage my team. And so that has, I mean, the investor that came in and my last series, we’d worked together for, you know, 15 years ago. And so, having built those relationships and built that trust over time is really critical. And I think a lot of times we think, okay, well, we’re going to come into a pitch and somebody is going to be willing to give us five, 10, 15 million dollars.

And the reality is it’s about building that engagement, that trust, that relationship with those investors. And I think doing that early and often and putting yourself out there is, is really, really critical. And I think for, I will say one of the things, uh, that one mistake I definitely make is you know, there are so many amazing female investors now, women led venture capital firms or impact firms. And I would think, Oh, this is where I’m going to get my money, right? They’re going to see how amazing I am and how amazing our business is and what this vision is. And, and it’s almost like you put your eggs in those baskets and you know, for some folks, that’s great. But at the end of the day, the investor wants to see who you are, what the business is, and it’s got to align to their themes. And so, you know, I always, I had this conversation with a young CEO uh, male CEO at ASU GSV. And I said, look, you know, the thing is you have to have a ton of perseverance, a ton, a ton, a ton, right? You have to have really thick skin and then be open to anything because in some cases the money’s going to come from a place that you don’t expect it to. You know, and so don’t make assumptions that it’s going to be this makeup of investor or this makeup of fund, you know, be really creative about how you approach things and find people who are really passionate about the work that you do.

It’s a really important part of the process. 

[00:21:04] Debbie Goodman: Those and many other learnings, but yeah, I agree there. Listen, there are some funds that they’re their mandate is to invest in diverse founders, in which case you probably will have a better shot if you as a woman, but yeah, to ultimately they’re even female founded funds and investors are going to put their money where they believe there is a big growth story ahead. So, it’s definitely not going to be a charity case. Right. Point around building relationships. I’ve heard this over and over from investors because I interviewed so many investors on this podcast, and they often say that they invest in people who’ve stayed in touch over time, and who have built a relationship over time and who they didn’t give money to at the very beginning. And so I think that for founders to actually build in some kind of like CRM, stay in touch, a system to make sure that they really are letting investors know what they’re up to, because there’s going to come a time in the future when perhaps they will get a yes. And no, it’s not a no forever, it’s just like, it’s not now. 

[00:22:07] Sara Leoni: No, yeah, not right now. No, I totally agree. And I’ve done some of that. I could be better, you know, but I definitely have my list of folks that I will send, you know, maybe not quarterly, but every so often just a quick touch base of, hey, here’s how we’re doing. Here’s where we said we were going to be right. And it, and it provides an opportunity to hop back on a Zoom, which takes, you know, no time at all. But those relationships are really important. I definitely can’t stress that enough. 

[00:22:39] Debbie Goodman: Okay. So I want to talk about your core values of creating workplaces where people love to work because you and I speak the same language around that.

But that’s really hard sometimes when you’re also striving for high growth. We know that startup life can be absolutely brutal, no balance, lots of sacrifice. So what does it take to build a high performance, high growth team, but also have a culture where people are loving their, their work lives. 

[00:23:07] Sara Leoni: Yeah, it’s such a great question. Actually, when I saw this question my first inclination was, well, I should ask my team, right? I should ask my team. What, what have we done that you really value? And I did. And I got an amazing amount of feedback. I’m going to turn it into a blog post at some point. But I mean, I think part of this is, you know, I’ve heard the term authenticity is overused, but at the end of the day, as the CEO, I am setting the culture in many ways, right.

Out of my actions, out of the team that I build, right. The leaders that I bring into the organization. And for me very early on I wanted to build a culture that was very open, that was very honest, that was very transparent where people could come in and they could be themselves. You know, we say we have a no BS culture, right? Some people love that. Some people don’t. My team happens to love that, right? We’re all going to be incredibly direct with one another. We are in it together. Uh, humility is one of our core values, right? It’s very important. We, I do not want to build an organization where politicking or bureaucracy plays a role. It’s like, check your ego at the door. There’s no I in team, right? We’re all showing up together to have one another’s backs. And you know, that in being in being transparent, not just with the good. But the bad too, you know, I walk everybody through everything. They see the board deck. They, I give them feedback in terms of, you know, if I’m hearing something from the market, that’s not great.

I want the more informed I can have the entire team. And I just don’t mean my executive team. I mean, the entire organization the better aligned we are, right. As we’re thinking about where our focus areas are or what we’re building towards. And I have found again, that’s to some degree, that’s the operator in me.

I want to make sure everybody’s highly, highly focused and that they’re, you know, we’re not off like, you know, trying to, to chase the squirrel that’s in front of us that looks really exciting. Right? That looks really intriguing, but the reality is it’s not going to create value for the organization. So there was a couple of things that the team highlighted, in just some quotes that I wanted to share. One was you know, outside of those things, which, you know, kind of encompassed one was, we can’t promise it will always be fun, but you will definitely have fun. Right? Like this is hard. This is hard. And not every step in the road is going to be great, but at the end, when you’re able to step back and really look at what we’re accomplishing, it’s incredibly impactful. 

[00:25:49] Debbie Goodman: Okay. So I think that’s like, type 2 fun like ziplines. Like it’s pretty terrifying, a little hardcore, but afterwards it’s going to go, wow, that was fun.

[00:25:57] Sara Leoni: But afterwards, yeah, yeah. When you’re maybe enjoying a cold beer or just even, you know, sitting back and resting for a bit and looking back on what you accomplished. Yeah. It’s really fun. I think the other one is somebody said that, you know, I really recognize people who are in the weeds every day operating and that they may have different and very valuable insights. And, you know, I’m interested in those insights, right? I don’t want this to be a top down organization. I want this to be very much a, there’s going to be some top down and there’s going to be a lot of bottoms up. And so how do we take that feedback and really act on it? And that was one of the things I heard kind of continuously is it’s not just lip service. It’s not just me saying, how do we get better? It’s they hear me ask, and then they see pretty immediately the actions that we put in place. And the last one that I just loved is you are changing and growing with us, not away from us. And, you know, I think that there’s a lot of value in just staying really close to the organization and really understanding what the organization, you know, what, where’s the heartbeat of the organization and are we truly living the values that we put on the website or is it just you know, is it just a poster board for what we want to aspire to be? And you know, we don’t want ours to be aspirational. We want to be living them every day. 

[00:27:24] Debbie Goodman: Yeah. Well, I love the fact that you actually asked your team. I think I I’d be interested to know if most CEOs did that on a, you know, a regular basis without the sort of like the automated versions, the culture amps, et cetera what they might discover. And whether they would get accurate feedback. So the fact that you got some really good feedback in itself is a good indication of the kind of culture you have there. So kudos to you. Okay. If all your hopes and dreams materialize, Sara, what does Ziplines Education look like in, let’s say five years time? 

[00:27:57] Sara Leoni: Yeah. You know, the things that we’re really setting out to accomplish is obviously at our North Star student outcomes, right? It’s really impact in the industry and how we’re helping people realize the goals that they want to accomplish and so that will always be at the centre of what we are striving for. I think from a, uh, you know, pragmatic, practical perspective, you know, we have 26 amazing university partners today. They span a number of regions across the US. We have an opportunity to touch every part of this country in a meaningful way and in five years, I want to be there. You know, I want us to be thinking about how do we provide not just a portfolio of courses, but really a very data driven, highly configurable learning system that enables people to really accomplish their specific goals. Right. And, and today we do that in a broader sense, but I think there’s a huge opportunity for us as we think about these very regional kind of community based relationships that we’re building to be able to tie those skills directly into employers looking for those jobs. And so there’s a lot of connective tissue elements that we’ll be building across the next five years. And then, you know, I think on the horizon is really thinking about look, we are seeing people, whether they’re getting more responsibilities or they’re getting promoted in their jobs, or they’re going into a new company. How do we help those companies continue to upskill the employee base they have. How do we help them stay relevant? And there’s a huge opportunity for us to really build those relationships again, both on the front end of making sure that we’ve got a strong employer network to connect folks to, but then also thinking how do we help them continually evolve so that they can achieve their goals. So there’s, you know, outside of that, there’s like, there’s so many different things. It’s very exciting. 

[00:30:03] Debbie Goodman: It sounds very exciting. Sara, we unfortunately are out of time. But this has been a fabulous conversation. Thank you so much for all the pearls of wisdom. Some very hard ones, I know, but hopefully we have been able to share some good nuggets of gold with the listeners. Have a wonderful rest of your day.

Sara Leoni: Yeah. You as well. Thanks again for having me. 

Okay. Bye now. 


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