She never planned to be a CEO. Then a career built on execution - and a softball glove - carried her from a $50M textbook business to a company retooling 20,000 adult careers.
Sara Leoni likes to explain her company by describing a moment of controlled terror. You clip into a harness. You step off a platform. There is a wire in front of you, a tree at the far end, and nothing but air in between. "Learning is a journey," she says - "intimidating, exhilarating, challenging and continuous." That is the whole pitch for Ziplines Education in one sentence, and it is also, near enough, the story of how she got here.
She never set out to run a company. Ask her and she will tell you the CEO title arrived the way most good things did in her life: by showing up, doing the work in front of her, and letting the next role find her. Twenty-plus years across management, marketing and operations - in big corporations and small startups - added up to a career before it ever added up to a plan.
Before the boardrooms there were dugouts. Leoni grew up in team sports - softball, soccer, basketball - and played softball at the Division I level for the University of Nevada, Las Vegas, where she earned All-American honors and, later, Alumna of the Year from the Greenspun College of Urban Affairs. She talks about athletics the way other founders talk about their first company: as the place she learned commitment, dedication, and what it means to show up for the person next to you.
The mantra she carried out of that era is short enough to fit on a wristband: leave it all on the field. It is not a motivational poster to her. It is an operating instruction - the reason she describes success not as a trophy but as a residue.
Leoni spent about seven years at Rafter, a course-materials and technology company that worked with hundreds of colleges. Her fingerprints are on the numbers: she scaled the direct-to-consumer business from $2 million to more than $50 million in three years, eventually running the company as CEO. Along the way, her teams helped nearly three million students save roughly half a billion dollars on textbooks.
But the textbook years taught her something the balance sheet did not capture. The price of a book was a barrier, yes. The bigger barrier was the gap between what a degree taught and what an employer actually needed. You could save a student $200 on a course reader and still send them into a job market that had moved on without them.
The market she saw is easy to state and hard to fix. Nearly all jobs now demand some level of digital fluency. A large share of workers simply do not have it. That mismatch - not tuition, not prestige - is the thing Ziplines was built to attack.
A ladder is the usual metaphor for careers - one rung at a time, straight up. Leoni picked a zipline instead, and the choice is deliberate. A zipline has a clear starting point and a clear landing. You can see where you are going before you leave the platform. The exhilarating, slightly terrifying part is the flight in between - which is exactly how it feels to go back to school as a working adult with a job, a commute, and, in her case, a full house at home.
In practice, Ziplines partners with universities rather than competing with them. The company works with more than 30 colleges to deliver industry-recognized certificate programs - AI, project management, business analytics, digital marketing - that a four-year degree tends to skip. Learners get a university-backed credential and, more importantly, skills that employers are hiring for right now. So far, more than 20,000 adults have made the jump.
Raising the Series A taught her a lesson she now hands to other founders freely. Fundraising, she noticed, has a hidden grammar. Women tend to pitch on attainability - here is what we can realistically hit. Men tend to pitch on possibility - here is how big this could be, feasibility be damned. Investors, for better or worse, respond to the second one. So she rewrote how she told her own story, leading with the vision instead of hedging it.
Her earlier mistake was quieter and, she admits, more expensive: she leaned too hard on other people's opinions and let the noise drown out her own read of the business. A first-time CEO learns to listen. A good one learns which voice to trust.
Ask Leoni who she would most like to sit down with and the answer is not an investor. It is Sam Altman - and not to pitch him. She wants to argue about the thing that keeps her up: as generative AI rewires work, who gets left behind, and how do you build a transition that is humane instead of brutal. Her courses lean into it directly, teaching AI fluency, prompting, and no-code automation so that people learn to use the tools before the tools learn to replace them.
It is a bigger ambition than certificate enrollments. She talks about wanting to inspire "a movement dedicated to humanity and compassion" as technology reshapes the world - the belief that whether change helps or harms comes down to how thoughtfully people manage it.
Off the clock, the competitive streak stays on. Leoni is a mother of five sons and fits travel, skiing and hiking around the company and the household. She does not perform balance so much as keep showing up - the same rule from the softball field, applied to a life with more moving parts than most. She is quick to credit the people around her, including her COO Juli Zarzour, whose partnership she describes as built on mutual respect and a willingness to challenge each other productively. A note on Zarzour's desk - "I never asked to be the world's best boss, but here I am absolutely crushing it" - is the kind of thing Leoni points to when asked what keeps her going.
The through-line is simple enough that Leoni can say it in nine words, and does. Education creates opportunity. Opportunity unlocks social mobility. Everything else - the partnerships, the certificates, the Series A deck - is just the harness and the wire. The point is getting people to step off the platform and trust that there is a landing on the other side.