The idea of starting your own business for anyone can be a challenge and a pipedream, and CFOs are no exception. But for CFOs who also want to run the startup as CEO, there are additional leadership challenges. While the perspective gained working as a CFO can be invaluable in the transition, especially the experience gained via areas such as cash management and FP&A, running the entire show, creating a mission statement and guiding principles, and building a team is filled with pitfalls.
After a decade-long career as the finance chief of the small business lender OnDeck, Howard Katzenberg, now CEO of Glean.ai, watched one of the U.S.' largest small business lenders rapidly grow.
Katzenberg had to roll up his sleaves at OnDeck to achieve incredible growth, an IPO, and then a major acquisition. In his new endeavors, which includes starting his own fintech that specializes in accounting development software, Katzenberg brings that same mindset to the CEO position.
Howard Katzenberg
CEO, Glean.ai
- First CFO position: 2008
- Notable previous companies:
- Better Mortgage
- OnDeck
- American Express
This interview has been edited for brevity and clarity.
ADAM ZAKI: You have a well-rounded set of experiences. Which one of your previous positions do you credit as being most valuable to your success in corporate finance?
HOWARD KATZENBERG: Definitely my experience at OnDeck. It’s because I didn’t have professional finance experience when I started there in 2008. I was hired to run business development for OnDeck, but when the Great Recession hit, it was clear they needed a finance leader to better forecast the business and support the CEO with fundraising, and I raised my hand. Because I needed to learn everything about scaling financial operations and becoming a CFO on the job, it was the most valuable experience.
You held the CFO role at OnDeck for over a decade. CFOs rarely stay in a role for that length of time. What kept you there for that long, and what advice would you give CFOs who are frequently looking for the next best role?
KATZENBERG: I was at OnDeck for 10 years, but what made OnDeck such an amazing experience is that each year was different. I was one of OnDeck’s first 10 employees. When I left in 2018, we were publicly traded on the NYSE, had hundreds of employees, and offered our products in three countries. Strategically and operationally, I was involved in all aspects of the growth that occurred in between.
So the advice I’d give to fellow CFOs is to not focus on their length in the role, but on the underlying KPIs — are you learning new things every year? Are you taking on more responsibilities? Is your team growing? Are you having the impact you want? These are the things that matter.
What skills do CFOs possess that can make them successful CEOs? What value do you believe finance-centric people can bring to other leadership roles within a company?
KATZENBERG: CFOs understand how all parts of a business fit together. This allows them to see opportunities (and traps) from a perspective other execs may not have. CFOs also understand the importance of developing a strong business model with scalable distribution and profitable unit economics.
So from day one, CFOs are often thinking strategically like a CEO. Just as important, CFOs are people leaders. They manage finance teams, investors, auditors, Board members, etc., and need to foster strong relationships, influence peers, and inspire their teams to perform to the best of their abilities.
Accordingly, just being a leader is a skill that’s highly transferrable from CFO to CEO.
Your academic background is impressive — would you do anything differently?
KATZENBERG: I consider myself very fortunate to have attended the academic programs I did. My course of study was very focused on business as an undergrad. If I were to do it again, I’d take more math, history, and philosophy classes.
That said, I deeply value the time I spent at Cornell and Penn.
What are your goals now as a CEO? What advice would you give other CFOs looking to make a similar career transition as you?
KATZENBERG: I work with a great team at Glean.ai. We’ve been able to build the first intelligent AP tool that helps companies pay their vendors less. Our customers really love it. Unfortunately, no one’s ever heard of us. So my main goal currently is to build awareness of Glean in creative and low-cost ways.
My advice for other CFOs considering the leap to CEO is to get practice now. Spend more time with your sales, marketing, engineering, etc. teams. Understand what makes them tick and ask how Finance can better partner with them to achieve their business goals.
Better team collaborations will be great practice for when you’re in the CEO seat.