The value of versatility: How a broad skillset boosts a career in fintech

Although it’s difficult to predict what Derek Bowerman, a Collateral Management product manager at Calypso Technology, will be able to accomplish next, it’s a safe bet it’ll be something exciting. Derek has been with Calypso since graduating from college over a decade ago, and he has already held a wide range of roles on both coasts. His varied experience has given him both a versatile skillset and a promising career trajectory.

Investment banks are increasingly shifting commoditized tech jobs to lower-cost destinations. The roles that will survive in major financial centers long-term are client-facing or niche skills that are difficult to find elsewhere.

When planning your career path, it’s important to strike the difficult balance of specializing to become a subject-matter expert while also avoiding pigeon-holing yourself.

Staying informed is critical

Regular interaction with clients is the key to understanding their issues and figuring out how to resolve them.

“The best way to learn about the market is to directly interact with the market participants,” he said. “At Calypso, we are constantly working with the clients and gaining new insights into their challenges.”

For example, recently there have been many new regulations that apply to financial services firms, so Calypso employees have been in regular communication with clients in every region of the world to gain perspective on how markets react to and comply with new regulations.

“If you’re not up to date on what your clients need, then you’ll begin to lose relevance as well as your client’s confidence,” Bowerman said.

Shifting responsibilities

Bowerman credits his ever-shifting roles and responsibilities at Calypso with helping him to acquire and maintain a broad skillset. He has been with Calypso for almost 15 years.

“I started my career at Calypso fresh out of college when it was still a relatively small company of less than 40 employees worldwide,” he said.

Bowerman’s first role was working as the assistant of the office manager, who also acted as the manager of the HR, finance and accounting departments. After his boss left the company, Bowerman took over as the office manager.

After about six months of that, he started testing Calypso’s internal website for bugs as a side project, an endeavor which caught the attention of the CEO.

“I guess our CEO was impressed with the number of issues I found, as he gave me the opportunity to move over to the product side of our business as a QA analyst,” Bowerman said. “I spent a little over a year working in QA, which gave me a great understanding of how the different financial products worked, and this really laid the groundwork for my current financial-markets understanding.”

Bowerman was then presented with the opportunity to transition to the company’s helpdesk team.

“This was a great experience as well, as it allowed me to directly interact with our clients, understanding their pain points and gaining a greater appreciation for how the market was using our products and how they could be improved,” he said.

After about a year and a half on the helpdesk team, Bowerman relocated to Calypso’s New York office to take on a professional services role, where he worked onsite with several clients, getting hands-on experience with how trading desks used the software, including post-trade processing.

“By working closely with the banks’ business analysts, my knowledge of the financial markets continued to grow,” Bowerman said. “This also enhanced my understanding of how clients were actually using the system, seeing pain points like how many clicks it was taking them to do tasks they performed 50 times a day.

“It was invaluable experience, and it really gave me an understanding of how the usability of our software impacted our clients,” he said.

Bowerman spent about two and a half years working in professional services before transitioning to Calypso’s fixed income and securities finance team as a business analyst. Working with a specific product allowed him to focus his knowledge in a single area to gain real expertise.

Over the next four years or so, Bowerman gradually transitioned to a senior business analyst role, ultimately working on collateral management. He has spent the past four years back in San Francisco as the product manager for Calypso’s collateral solution.

Mentorship leads to career success

Having good mentors is critical to success, since anyone starting their career needs to see how successful people function and how they’ve reached their respective positions.

“Throughout my journey at Calypso, the one constant I’ve had was the luxury of reporting to an excellent set of managers – real mentors who helped shape the person I’ve become, leading by example, and guiding me along my way, so I’ve been extremely fortunate in that respect,” Bowerman said.

“My career path with Calypso will help me in the future because I’ve worked in so many different parts of my organization, so my future possibilities both inside and outside the company are wide open.”