Last month, we announced we led the $6.4 million Series A in Ziplines Education, a continuing education company challenging perspectives in education for the digital age.
As Derek Newton at Forbes said at the time, “the investment is a major signal about where the betting money is going in higher education – fast track, high impact, career training.”
JSV’s Co-founder and Managing Director, Greg Gretsch, who led the deal, recently sat down with Ziplines CEO Sara Leoni to talk about the company, its position in the market, and where education is going on the heels of so much transformation. Read their conversation below.

GG: Let’s start by having you tell us a little bit about Ziplines Education. What are you and the team building and why?
SL: Ziplines Education is a continuing-education company that partners with universities to deliver industry-focused certificate courses that prepare professionals for today’s digital-first workforce. We help individuals realize and achieve their career aspirations by helping them develop the relevant skills and experience they need to pursue the career they’ve always wanted.
If we take a step back and think about what’s happening around us — 92% of jobs analyzed require digital skills, yet one-third of workers don’t have the foundational digital skills necessary to enter and thrive in today’s workforce — technology is evolving at breakneck speed. No matter how proficient you are in your current role, your skills and capabilities have a limited shelf life.
We’re building the one-stop shop for aspiring business professionals to develop the skills, knowledge, and confidence they need to succeed in a technology-first future of work. Our approach to learning is pragmatic, hands-on, and community-based, delivering immediate impact to our learners.
GG: You founded Ziplines Education after a seven-year tenure at Rafter. What motivated the change and what was the transition like?
SL: Wearing many executive hats at Rafter, a course-materials management platform serving higher education, I had the opportunity to build the direct-to-consumer business from $2 million to over $50 million in just three short years. In doing so, we helped nearly 3 million students save over half a billion dollars on their textbooks — the experience was exceptionally rewarding.
During my time there, I saw firsthand how expensive acquiring a degree can be — and, at the same time, the opportunities that high-impact education can unlock if accomplished successfully.
With Ziplines Education, we are tackling a huge, untapped opportunity to more closely align industry with our higher-education system. The potential to help aspiring professionals gain sought-after skill sets that aren’t typically taught in a traditional four-year degree program. An opportunity to help bridge a widening skills gap and equip the workforce with the knowledge, skills, and hands-on experiences needed to be confident and prepared for a successful career.
GG: How has growth been over the past few years? What sort of impact did the pandemic have on your business?
SL: In the past two years alone, we’ve grown our enrollments by 3x. In large part, this is due to our expanding network of incredible university partners and our growing catalog of highly rated courses—more than 90% of students tell us they’re applying what they learned in class to their jobs, which is both rewarding and validating.
As for the pandemic, it had a lasting impact on our business. It made online learning palatable and acceptable for the vast majority of the market. Seemingly overnight, learners had to make the significant shift from a physical classroom to being fully online and remote. And, while many didn’t get it right, we took the opportunity to zero in on what adult learners wanted most from this new world of learning: flexibility, support, practicality, approachability, trust, and, last but not least, affordability.
GG: You’ve said before that Ziplines Education aims to be the engine behind courses and programs offered by colleges, not compete with them. What’s it like selling into these institutions?
SL: Undeniably, there’s a huge opportunity in the alternative-credential space and an even bigger opportunity for higher education to play a role. However, the challenge for universities is they can’t move as quickly as we can, nor have the capabilities or the resources to continuously update their curriculum at the scale and price point that adult learners demand. We’re helping them close a massive gap that is critical to their institution’s future, while providing them with a new type of student, typically served outside of higher education, enabling a net-new revenue stream.
We’re helping these institutions stay relevant — if not essential — to the workforce and to employers. And, to me, that’s really important. Seeing the impact with students, both immediate and longer-term, as well as the outcomes we help to enable for our partners, is really what fuels my passion for this company and its mission.

GG: Upskilling has become increasingly popular among professionals, with some saying skill-based certifications in topics like AI give them a competitive edge. How do you see Ziplines Education fitting into that conversation?
SL: We are at the beginning of a wave of massive change, and it’s nearly impossible to predict all the impacts it will have. Generative AI has the power to completely overhaul the workforce as we know it. Jobs will be created. Jobs will be obliterated. Staying ahead of the curve and predicting future possibilities is going to be the key to survival — and success. We continually hear from the students we serve that because of our unique offerings, they feel more confident and equipped to take their careers to the next level. We’re excited to partner with dozens of leading universities to innovate on their behalf, while offering a fresh and relevant catalog of programs to the growing tech-adjacent workforce.
GG: There has been a lot of turmoil in the online education market in the last few years. Is that turmoil a problem or opportunity for Ziplines Education?
SL: We are always keeping an eye on the market, especially the successes and pitfalls of its major players. What sets us apart is our pragmatic, real-world curriculum, persona-driven pedagogy, and laser focus on both student and institutional outcomes.
So many learning platforms offer passive learning, which won’t prepare you for what it takes to actually succeed on the job. In a Ziplines Education course, you are embedded in an active, hands-on learning environment. You’ll join a community of learners who are supported by subject-matter experts and success advocates who help you every step of the way. You’ll have an opportunity to network with peers and learn from other professionals around the world.
As an organization, we are laser-focused on our students’ success and the success of our university partners. We are heads down, working to create the best company, products, and team. Everything else is just noise.
GG: How do you see the online education market evolving over the next 10 years?
SL: According to the World Economic Forum, more than half of our workforce requires new skills in order to keep up with the ever-evolving demands of industry. The reality is that with the acceleration of technology, platforms, and innovations, such as generative AI, embracing the rate of change is table stakes. Jobs are changing. The skills required are evolving. What we know today will be obsolete a year or two from now. Our goal is to continue to innovate and help the workforce stay relevant and in demand — and confident about taking on what’s ahead.
We know that our higher-education systems need to evolve. We see an opportunity to support that evolution and play a critical role by more closely aligning institutions and instruction with jobs, industry, and what will undeniably be a digital-first future.
GG: Ziplines Education is tapping into some undeniable cultural shifts. What’s the end game?
SL: We want to be the destination for people to discover and learn new skills so they can be confident and enjoy long, successful careers. We are laser-focused on finding the right university partners and expanding our product catalog into high-growth areas where we know we can help people build the foundational skill sets they need to parlay knowledge into outcomes. This goal may be reflected in a new job, a promotion, or just being more confident and excited about applying those refreshed skills in their existing role. Our mission gives us the firepower to invest in those areas and to stay focused and intentional in doing more of what we’re already doing, while servicing our students and university partners in better and more meaningful ways.
GG: What advice do you have for other entrepreneurs fundraising in the current economic climate?
Build your tribe. Find a support system. Learn from those who have both failed and succeeded.
What I found through my fundraising experience is the need to project the utmost confidence. Lean in and fully believe in what you’re doing, even if you don’t yet have concrete evidence your idea will succeed.
Apropos of Women’s History Month, there’s a common saying among women founders: “The challenge is not the founding, it’s the funding.” Fewer women-led businesses get the funding they need. I believe this is partially due to the fact that men and women often have different approaches to fundraising. As women, we want tangible proof points that we are absolutely capable of accomplishing the vision we set with investors. We want a clear roadmap and milestones with the utmost confidence we can deliver what we promise. On the flip side, our male counterparts are often willing to share a vision with their potential backers, even if that vision may be unattainable. Put another way, when men are pitching, they emphasize possibility versus attainability.
I have told many female founders that when they pitch, they need to lead with equal parts possibility and confidence. Women need role models who can help them strike this balance. That stark reality finally became clear when I had an opportunity to see an incredible, confident female CEO run through a practice pitch—the pitch she’d used to successfully close an $8M Series A round. That was the moment I finally understood the kind of energy that was required.
GG: What’s the most important thing you want people to know about Ziplines Education?
SL: Our mission is to help individuals gain the digital skills and real-world experience they need to thrive in careers they love. Every student who completes one of our programs has the opportunity to achieve more through that experience. Education creates opportunity. Opportunity unlocks social mobility.
The only way we can accomplish our mission is by hiring and motivating an incredibly talented team. Every chance I get, I want to thank my team for their hard work and dedication to our mission. Together, we are creating change and opportunity for those we serve — they’re all amazing, and I’m proud to be on this journey with them.

