Insecurity breeds security — Imposter Syndrome affects CEOs too. I made many mistakes as a first time CEO and attacked every day with a healthy dose of paranoia. While it’s important to show confidence to the team and “fake it until you make it”, the best leaders use self-doubt to improve. Fear forces you to approach everyday with humility, candor, attention to detail and urgency.
As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Jared Kaplan.
Jared Kaplan is CEO and Co-Founder of Indigo, an AI-powered insurtech platform for medical malpractice insurance, and he served in executive roles at several private equity-backed fintech companies prior to founding Indigo. Notably, Jared was CEO of Cadre, a tech platform facilitating access to commercial real estate investment, he was CEO of OppFi (NYSE: OPFI), an AI lending platform powering community banks, and he was Co-Founder & EVP of Insureon, the leading online agency for small business insurance. Jared holds a BBA from the University of Michigan.
Thank you so much for joining us in this interview series! 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?
Today, as CEO and Co-Founder of Indigo — an AI-powered insurtech platform that is revolutionizing medical malpractice insurance — I look back on my long career as a tech entrepreneur and investor in old school industries, and I credit a lot of my ambition to my family and the way I was raised. I grew up in the Midwest and I’m an identical twin. On one hand, my parents expertly balanced their careers with family time, which set a great example for my brother and myself. On the other hand, being an identical twin meant that I had someone to healthily compete with in my formative years. This pushed me to maximize every ounce of my potential, and I continued to have this mindset and work ethic when I studied at the University of Michigan’s Ross School of Business and when I started my first job out of college in New York.
After graduating from college, I spent a decade working in New York at Goldman Sachs and Accretive, a private investment firm. While at Accretive, I co-founded — Insureon, an insurance business that went on to become the fastest-growing agency in P&C insurance and was eventually sold to Hub International and Bold Penguin. I then moved on to my first CEO gig at OppFi (NYSE: OPFI) — an AI lending platform powering community banks. Taking my first CEO role was a huge step for me and I learned a lot about myself and my leadership style. We took the company public in 2021, and then I moved to Cadre — a venture capital-based real estate startup. In 2023, I joined Indigo, and it’s been an exciting adventure. It’s my first time working in the healthcare space, but I’ve been able to leverage my experience as CEO and years working across insurance, technology and financial services as I’ve found the product and industry might change, but the playbook doesn’t.
Can you share the most interesting story that happened to you since you began leading your company?
Medical Malpractice is a stone age industry devoid of investment and technology talent. As a result, there have been virtually no new entrants in the last decade. With our automated, tech first approach to procurement and risk segmentation, we’ve gained profitable share quickly, and that makes the incumbents very unhappy! While I’d heard stories about large companies in established industries trying to kill start-ups through tarnishing brand and lawfare, I never had the privilege of experiencing it until now. If the multi-billion companies are worried about little ol’ Indigo, we are absolutely on the path to creating something magnificent!
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
At Goldman, I learned very quickly that despite sleep deprivation, “attention to detail” was not a choice! I remember finalizing a model and pitch book around midnight and then having it printed and delivered to the Managing Director ahead of his flight for the following morning’s meeting. Shortly thereafter, something didn’t feel right and I went back to double check my work — there was a huge error. What do I do? I stayed up all night tossing and turning and at 7am informed the MD of the issue so he could mange the client in the meeting. Not a fun conversation. Later that afternoon, he called the VP to discuss what happened; however, he didn’t realize I was also on the line. It was a real-time performance review and it was NOT pretty. But it changed me forever — and made me much better at catching mistakes myself before others.
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?
My Dad is a physician and has had a long career making life and death decisions. So, when I have business issues, or really any issue, he is always able to reframe the problem with a lens of what really matters. I love what we are building at Indigo but none of our problems equate to the decisions doctors make on a daily basis. Hopefully, our product can help make physicians’ lives easier because they deserve it!
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?
At one point early in my career as a CEO, we uncovered a group of individuals in a critical division of the company faking numbers to maximize their incentives. Do we let it slide so that we have no business interruption or do we hold the individuals accountable? We made the decision to hold the individuals accountable, which decimated part of our business for a period of time. But the impact on our culture proved more valuable than the loss of business.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
When I first became CEO, the majority shareholder accurately alluded the role as a “composer.” A CEO is the only leader at the company that has full visibility across all domains and directions. And they are the only employee that ultimately controls all resources. Signing up for that means you have full responsibility for all outcomes and the vast majority, if not all, of your focus is on key issues. That being said, given the breadth of your duties, you can’t solve issues yourself and must rely on a team that thrives on autonomy and taking ownership to ensure continuous improvement (and harmonies!) over time. Ensuring you have the right musician in every seat is the only variable that matters when creating value.
What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?
Many employees in an organization are afraid to “bother” the CEO. They fear the role is too busy and high level to care what they think. The most successful CEOs are dying to understand what is happening at the ground level, especially as it pertains to customer value creation. It’s true that most CEOs never receive the full truth from employees. You get input and perspective from different employees that add up to the truth. And the more data and anecdotes a CEO gathers, the more likely they are to understand the situation and make a good decision.
What is the most striking difference between your actual job and how you thought the job would be?
The biggest misconception I’ve realized is the role a Board plays in governance. There is no way any Board can understand the thousands of micro decisions and actions that lead up to company outcomes. Many CEOs make the mistake of lacking conviction with a Board. They ask for advice instead of presenting a thoughtful roadmap with conviction. By design, a CEO has the most information on the playing field and is in a much better position to articulate why the company should choose a certain path. A Board’s role is to mutually ensure with the CEO what milestones and targets define success. CEOs figure out the visions and pathways to reach them.
Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive, and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
I don’t know that everyone is cut out to be an executive nor that everyone wants to be an executive, but I have found that people that stay humble and curious are more likely to be successful in an executive role. When people can do this, even when they are at the highest level within an organization, it drives better outcomes, empowers employees and creates a transparent, collaborative work environment.
What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?
I want people to come to work excited and to take pride in their work, and we’ve worked hard at Indigo to build a company culture that enables this. I believe autonomy and transparency are key, and transparency can come in many forms. For example, I have prioritized transparency by setting clear priorities for teams. This way the goal post doesn’t keep moving and expectations are always clear. Another key part of leading with transparency is accepting feedback. I believe constructive feedback is a gift and leaders must empower employees to speak up when something isn’t working.
How have you used your success to make the world a better place?
I try to use my success to create opportunities for others — whether that’s mentoring younger professionals, supporting causes I care about, or making sure the people around me feel encouraged and valued. Along the way we have enabled hundreds of jobs and created value for investors, freelance businesses, non prime consumers and physicians.
What are your “Five Things I Wish Someone Told Me Before I Became A CEO” and why?
1 . Insecurity breeds security — Imposter Syndrome affects CEOs too. I made many mistakes as a first time CEO and attacked every day with a healthy dose of paranoia. While it’s important to show confidence to the team and “fake it until you make it”, the best leaders use self-doubt to improve. Fear forces you to approach everyday with humility, candor, attention to detail and urgency.
2 . Success is not a straight line — more often than not, setbacks lead to higher peaks. How you respond to failure is critical to building trust with the team. At Indigo, we fail every day when don’t win an account that has a no-brainer value proposition. There a number of reasons why this happens including lack of brand awareness, discomfort with a startup, or an insurance broker did not pound the table. If we understand why a customer says, “no”, we can build a playbook to improve those weaknesses.
3 . Use your bullets wisely — many times before I was a CEO, I would have a million things to do and then my manager would add another key project or workstream. It was incredibly demotivating. Everyone has a breaking point and the goal of a CEO is to push the team with achievable goals that are comfortably uncomfortable. If everything becomes a priority, nothing gets done on time with accuracy. A clear, prioritized approach allows a CEO to really lean in and challenge the team for the projects and timelines that really matter.
4 . Never lose sight of the details — as a founder CEO you are the expert of all things at the company. As the company scales, there is necessity to leverage executives to drive scale. But it is never an excuse to move away from the details — specifically, deeply understanding how customers respond to your product. Scale is not an excuse to see the forest from the trees. Always know what trees are in your forest!
5 .If the numbers seem too good, they probably are — when the number are worse than expected, CEOs react swiftly to determine root cause. When the numbers are better than expected, they are typically taken for granted. In reality, this is often a red herring that the data is incorrect. It’s important to know actual outcomes from expectations whether good or bad.
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.
I would inspire a movement focused on making high-quality healthcare and preventative wellness accessible to everyone. If we can reduce barriers — financial, technological, geographic — we can add years of healthy life to billions of people. Health is the foundation of opportunity.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
My favorite life lesson quote is, ‘Do what you say.’ Over the years, I’ve learned that success isn’t just about strategy or intelligence — it’s about reliability. When you follow through on your commitments, big or small, you earn trust. That trust compounds — whether in business, friendships, or family. For me, living by that principle has opened more doors than any grand vision alone.
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.
I would love to have lunch with Lin-Manuel Miranda. His work proves that storytelling can change how people see themselves and their history. He blends art, intellect, and accessibility in a way that reaches across generations and cultures. I’d be fascinated to hear how he thinks about creativity as a force for connection, and how he continues to reinvent himself while staying true to his roots.
Medium: Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
Image by MicroStockHub from iStock.
