Female Founders: Sara Leoni of Ziplines Education On The Five Things You Need To Thrive and Succeed as a Woman Founder

An Interview With Doug Noll

Once you’re a CEO, it’s hard to look back. Even though I never envisioned myself in this role earlier in my career, it’s the only job I could ever have. It would be challenging now to take a job working for someone else because I love the autonomy, I love building teams, and I love helping others seize new responsibilities, spread their wings, and grow.

As a part of our series about Women Founders, we had the pleasure of interviewing Sara Leoni.

Sara Leoni is CEO and founder of Ziplines Education, an education company that partners with universities to deliver industry-focused certificate courses that prepare professionals for today’s digital-first workforce. With a career spanning more than 20 years, she offers expertise in management, marketing, operations, and building innovative brands for major corporations, as well as startups. A passionate and inspirational leader, Sara thrives on building, focusing, and motivating high-performing teams to solve big programs, while delivering significant growth in high-impact businesses.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

In thinking back over my career journey, I never set out to become a CEO. In fact, what I loved was sports, having played softball, soccer, and basketball for most of my life. That said, the vision, mission, and values I hold today stemmed from these team experiences, all contributing to who I am as a leader. I learned that you need to commit significant time and energy in order to improve, and you have to be prepared to show up for your team. I’ve carried these values into my work life, and I believe they are what drove me to my current role as CEO and startup founder.

However, for me, being a successful CEO isn’t a goal in and of itself. Instead, success is a byproduct of the process of working toward a goal, and the people who help and push you to get there. I’ve been lucky to work beside and lead great people throughout my work and personal life, and they have enabled me to excel in my career. My mantra is to “leave it all on the field,” as we say in sports, and my cumulative experiences have taught me what great leadership looks like.

Can you share the most interesting story that happened to you since you began leading your company?

I find launching a company — when founders are trying to determine their product-market fit — to be the most interesting and yet the most challenging stage. As a founder, you have an idea of how to build a business. You can see the opportunities, as well as the huge potential. In reality, though, not every company reaches its potential. At this early stage, you need to set hypotheses, test them, and iterate on ideas. You need to find the resources to get that done and be honest with yourself about what’s working and what’s not. That last bit is hard given we all want our “best” ideas to work, even though sometimes they don’t.

Also, this stage can be particularly volatile and emotional. I’ve been part of many startups, and the beginning of every organization is like being on a roller coaster. One day, you could be feeling the highest of highs and the next day, you’re at the lowest of lows. The ambiguity and constant shifting at this stage of building a business can be trying, so you have to be able to deal with that energy.

Can you share a story about a mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The biggest mistake I’ve made is relying too heavily on other people’s opinions. As a leader, many people will offer their opinions about your business, and they present these ideas with such conviction that it’s hard to ignore them. It’s easier to embrace the doubt you feel — because at the early stages, you’re pretty sure everyone knows more than you. At some point, this noise begins to cloud your judgment, and you may even start to question your gut instincts and wonder: Is this the right strategy for the organization?

Unsurprisingly, there are cases where I have made decisions within the business that went against my gut instincts, and they were the wrong decisions.

What I’ve learned from these mistakes is that you have to trust yourself. You must remember that you know your business better than anybody else. And, while it is great to have smart people around you who give you sage advice, at the end of the day, it’s your job as CEO to take that advice and decide what pieces of it will be most useful to you.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I really value my Chief Operating Officer, Juli Zarzour. We have an incredible partnership because we have developed a deep respect for one another. We operate differently and we push each other in uncomfortable ways. And when the smoke clears, we always end up stronger, and with better results. I appreciate having her on my side because I know she’s always going to be honest with me. We also have empathy for each other as working mothers, and for the many different directions in which we are constantly being pulled. When I doubt myself, she’s there to pick me up. And I hope I do the same for her. Recently, she gave me a notebook with a quote on the cover, which said: “I never asked to be the world’s best boss, but here I am absolutely crushing it.” It’s those small gestures that can go a long way — and keep you afloat. They make you laugh and can lift you up during tough times.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

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 $8 million Series A round. That was the moment I finally understood the kind of energy that was required. As women, we need more of these role models so we can experience firsthand what it really takes to make it happen.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

We need to create different funding sources for businesses that have different objectives. Many women I know want to build businesses that could change the world or change lives. They are looking to create a meaningful long-term return on investment, but at the same time, they don’t have the ambition to create a “unicorn.” If investors understood the tremendous potential in these types of sustainable businesses and could create a different share class of investment for women-founded, women-led businesses, it could be insanely profitable.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

Women are incredible leaders for several reasons.

• Women have strong empathy for others. We realize that our people are our greatest asset in an organization. Understanding those who are different from you, and finding ways to communicate and connect with them, is an invaluable advantage.
• Strong emotional intelligence goes a long way. I know many women who, because of their experiences raising kids or caretaking, have honed the skills needed to make others feel comfortable and cared for, and this helps in all areas of life. We understand that it’s not just about work, and that balance has the potential to create harmony.
• Women are great multi-taskers. We have to bounce between kids, jobs, volunteering, caring for family, and many other responsibilities. Because of these constantly competing demands, we tend to be skilled at juggling, prioritizing, and understanding what’s most important in any given moment. Being able to multitask helps us focus on the right strategies required for growing a business.
• Humility is a huge asset. Leaders who demonstrate humility can build great relationships and create powerful and empowered organizations. Humility leads to vulnerability, which is another great advantage. I have found that many women leaders show vulnerability — they’re willing to share how they feel, when they need help, and where they have gaps. This kind of open, honest communication helps team members connect, be empathetic to the challenges folks are facing both inside and outside of the organization, and makes the whole work experience more genuine.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

• It’s all about the idea. You don’t have to create an entirely new universe in which people can operate in order to be successful. While having an innovative idea is obviously important, execution is key. Some people believe that a unique idea alone will guarantee success, but successful businesses are built on effective execution, market validation, and continuous iteration based on feedback.
• Founders only come from the best universities. Although many well-funded company leaders still tend to be from the most prestigious schools, they are not the only source of great talent. Your degree or pedigree does not define you. Not all of us started with the opportunity to attend an Ivy League university — and that’s fine. Some of the best talent comes from unknown places, degree or no degree, and as innovators, we need to embrace that.
• Founders must be controversial. You don’t have to have a polarizing personality to create change. Many leaders we see may develop a persona to get where they want to go and enjoy their reputation of being perceived as “challenging.” They project the idea that only someone who breaks the rules and steps on people along the way will be successful. This type of leadership isn’t healthy for anyone. What’s more, operating in this way doesn’t create significant, sustainable outcomes.
• Founders can’t be real people. Founders come from many backgrounds and experiences, and wear many hats: parents, grandparents, first-generation college students, high school graduates, etc. The key is being willing to take risks and put yourself out there. I’ve found that surrounding yourself with a team of talented individuals who share your vision and complement your skills is crucial for success.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

Some people are wonderful individual contributors and some are cut out for leadership. A good founder is creative, thoughtful, and ambitious, while also being able to deal with ambiguity. They need to be gritty, persistent, and willing to lay their reputation on the line. If you’re a founder and your company fails, you fail very publicly — and often, you fail alone, which is a scary reality. Failure doesn’t feel good and facing this possibility isn’t right for everyone. Founders often face unexpected circumstances that can affect their control over the business, which is why flexibility and adaptability are essential qualities for navigating these uncertainties.

What are your “5 Things I Wish Someone Told Me Before I Started” and why?

1. Being a startup founder is really hard. Whereas I never expected success to happen overnight, I did assume that successful founders achieve their goals quickly. However, I learned that building a successful business, especially a startup, takes years, and requires a ton of hard work, humility, and unwavering persistence.
2. You have the best vantage point for your business. Don’t always take what outsiders (or even insiders, like board members) say at face value. They have a limited view of your business. Listen and process — great ideas come from unexpected places, but make sure you go with your gut. You’re in that seat for a reason.
3. You will fail. It’s hard and it feels like you’re never going to be able to pick yourself back up again, but you must and you will, especially with a more realistic understanding of the challenges and opportunities involved.
4. It will be challenging to get through the initial stages of a company. Finding product market fit can be expensive and time-consuming. It can take years. I wish I had understood the statistics better when I started out. The truth is, 92% of venture capital goes to men, and 80% of startups will fail. So understanding those hurdles, and overcoming them, is an enormous task.
5. Once you’re a CEO, it’s hard to look back. Even though I never envisioned myself in this role earlier in my career, it’s the only job I could ever have. It would be challenging now to take a job working for someone else because I love the autonomy, I love building teams, and I love helping others seize new responsibilities, spread their wings, and grow.

How have you used your success to make the world a better place?

What we do at Ziplines Education is all about making the world a better place. 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.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

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.

Through all of this, I’d like to inspire a movement dedicated to humanity and compassion. Technology has the power to unleash incredible change, with both positive and negative results. We are at the precipice of that movement and it’s up to us to control tech innovation and navigate our way through the changes it will unleash. If we don’t manage this process thoughtfully, we’ll create a very challenging, chaotic world, and all of us will have to live with the consequences.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

At the moment, I would say entrepreneur, investor, and former president of Y Combinator, Sam Altman. He’s been such an incredible accelerator of the AI movement. I’d love to understand his vision for the future and how he expects AI to transform the world as we know it. What are the knowns? What are the unknowns? I’d also like to understand how he thinks about safeguarding those that will be most vulnerable to AI, including our children, and how we continue to teach our future workforce skills that enable a stronger, better humanity.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About the Interviewer: Douglas E. Noll, JD, MA was born nearly blind, crippled with club feet, partially deaf, and left-handed. He overcame all of these obstacles to become a successful civil trial lawyer. In 2000, he abandoned his law practice to become a peacemaker. His calling is to serve humanity, and he executes his calling at many levels. He is an award-winning author, teacher, and trainer. He is a highly experienced mediator. Doug’s work carries him from international work to helping people resolve deep interpersonal and ideological conflicts. Doug teaches his innovative de-escalation skill that calms any angry person in 90 seconds or less. With Laurel Kaufer, Doug founded Prison of Peace in 2009. The Prison of Peace project trains life and long terms incarcerated people to be powerful peacemakers and mediators. He has been deeply moved by inmates who have learned and applied deep, empathic listening skills, leadership skills, and problem-solving skills to reduce violence in their prison communities. Their dedication to learning, improving, and serving their communities motivates him to expand the principles of Prison of Peace so that every human wanting to learn the skills of peace may do so. Doug’s awards include California Lawyer Magazine Lawyer of the Year, Best Lawyers in America Lawyer of the Year, Purpose Prize Fellow, International Academy of Mediators Syd Leezak Award of Excellence, National Academy of Distinguished Neutrals Neutral of the Year. His four books have won a number of awards and commendations. Doug’s podcast, Listen With Leaders, is now accepting guests. Click on this link to learn more and apply.