June 16, 2021

From the Bullpen to the Boardroom: Insights from CEOs

By Brandon Mavleos, Sr. Director, Product Marketing – IB & PE


In a recent webinar, Datasite sat down with three CEOs who started their career in investment banking. We sought to get their insights into how they leveraged their roles in finance to climb to CEO. As many professionals can attest, investment banking is a feeder job for other highly successful and ambitious career moves. However, the transition to get there is not always so clear, especially for aspiring entrepreneurs. The panel of experts broke down the challenges for our audience and offered several great takeaways for those who want to be CEO one day.

Maximize your banking years by focusing on the right skills

While the lifestyle, passion, and image of a tech CEO versus a banker have stark contrasts, the similarities are not to be overlooked. For example, whether you are building an Excel model or starting your own business, the diagnostic thought processes are critical. "The finance background lends itself to the operational rigor. As you are watching the physical or virtual widgets moving down the assembly line, having that analytical mindset really helps," says Matt Cooper, CEO of Skillshare.

In addition, investment banking helps young professionals refine and polish their relationship skills. As Jacqueline Hampton of Portico mentions, she had to learn how to manage "upwards, downwards and sideways, plus externally with clients and lawyers" in banking. This skill was even more important when she got into tech as she began to develop relationships with potential investors, team members, customers and other parties.

Other skillsets come nicely together between banking and entrepreneurship, such as doing regular competitive assessments and understanding a company's business and financial metrics. As Jacqueline mentions, "often founders don't understand the intricacies of financials and building their own models, especially scenario analyses" so this is a positive differentiator for those that are willing to take the risk into entrepreneurship.

Regardless if you want to make a switch as an Analyst/Associate, or later on in your career, as you are thinking about your next step, Brian Anderson of Beastcoast Gaming recommends "taking proactive steps in what you want to do, and figure that out as early as possible in your career." This will enable you to position yourself in the right industry and potentially work with clients who can help you achieve your goals (or potentially be a business partner) in the future.

Make the most out of networking events

As our panelists validated, networking can take many different forms. As Brian discussed, it doesn't need to come in the form of a massive in-person networking event. It can be a well-thought-out email that asks questions about the business or how the CEO is thinking about their vision. Another way to think of networking is how you add value to the people within your network and "try to do as many favors as possible in whatever capacity. If you are a junior banker, that might be connecting the dots between two clients… I met my co-CEO at a conference while I was still in banking." By doing some pro-bono work, the current CEO was impressed by Brian and decided to bring him on as co-CEO.  

As for in-person events, while they can sometimes feel a bit challenging, Matt talks about some ways to make the most of it. "Have lots of conversations about what you are interested in. That way, when you find the opportunity to have good conversations with the right people, you know what you are talking about."  Also, when you go to an in-person event, set some goals and "make yourself a quota… if you have 5-6 good conversations, you feel like you got something out of the event."  This notion is especially interesting for our audience, with only ~32% believing that they are good at networking. Jacqueline validates the need to speak with others frequently, offering the advice, "there are so many jobs out there, and the possibilities are limitless," and if you are thinking about a career move, "write in your notebook every night on a scale from 1-10 how much you like your job, and after about three months, use your technical skills to add it up, and that should give you a good idea."

Self-Awareness to drive leadership skills

All three of our panelists agreed that the leadership skills you gain in investment banking are very different from an operating company's expectations. "You have to recalibrate what people expect out of their work and what motivates them," says Matt. "People might be more mission-driven, and you need to speak in a language they know and believe in."

Without a ton of experience, this can seem tricky at first, but Jacqueline offers some words for advice. First off, she recommends watching people you admire, so you can build those skills when you are still in banking. But when you get into an operating role, it's essential to listen and understand how to best interact with your team. "There are all sorts of personality assessments you can do to understand how you can interact with your team." At the end of the day, "as a good CEO, you are thinking about how to motivate your team and get out of the way… then let them do the real job!"

As far as which traits are the most important for a great leader, we can debate all day; however, Brian mentioned that one of the most important is self-awareness, that way you can "understand what you are good at, what you are not, and then lean into those strengths while hiring people to fill in the gaps." This blends nicely with the CEO role, as you are constantly putting out fires and seeing what challenges arise daily. As Brian discusses, having this self-awareness and putting the best people in the right seats allows you to tackle all different problems.


Build your confidence to pursue your passions

While only ~15% of our audience commented that the next step in their career might be a founder / CEO, the panel all rallied around the idea of building confidence to help you pursue your passions.  Jacqueline recommends doing user testing to check out your business idea. "Walk up to random people in a Starbucks, see what they think," but paint it in a negative light to get honest feedback from people. "If you do that and it resonates quickly, that can start to build your business," says Jacqueline.  And if you are feeling unsure one day, go and talk to your customers, who will naturally give you a confidence boost!

Brian also talks about working on your public speaking and taking on opportunities in banking, such as presenting to clients and getting feedback from managing directors. One of the most challenging things is to maintain your confidence and conviction, "it's great to have a team of supporters who believes in what you are doing… and don't listen to the haters!"

And finally, when you do succeed, it's crucial to create a great culture and set of values in your company. Matt does a wonderful job of distinguishing between the two concepts noting that "culture is going to change, but values you need to keep coming back to as big as the company gets. Leadership sets the tone on what you value and reward, not just what you write on the website."

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