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Leadership Profile: Benjamin Bergeron-Osajie on a Unique Mission

ClearEstate’s VP Sales and Marketing understands the value of compassionate communications

Posted on November 5, 2021
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The challenge of introducing a product that manages clients’ most sensitive assets, guiding them through what is often the most difficult period of their lives, is not something the ClearEstate team takes lightly.

Communicating the company’s philosophy with tact and sensitivity is key, and that means implementing thoughtfully-considered, low-pressure sales strategies at every stage in the marketing funnel. It’s a delicate balance for the entire sales team and a priority for ClearEstate Sales and Marketing Vice President Benjamin Bergeron-Osajie, who began his career 15 years ago with an entry-level gig.

From Sales Rep to a Corner Office

A Quebec native, Benjamin began his university days with the intention of teaching secondary-level social studies, history and geography. But he only lasted one semester, switching streams to focus on a true passion: working as a professional musician.

“I decided to really give my music my all at the time,” Benjamin recalled. “That was my big thing, to become a full-time musician.”

Despite an “amazing journey,” he couldn't quite get his artistic career to lift off. Between two tours, he decided to take on a sales job so he could pay the bills while figuring out his next move. He had always excelled at “people jobs” and enjoyed the back-and-forth of finding creative solutions. Pretty soon, this stopgap job started to feel like a meaningful career.

Newly-listed on Nasdaq (NVEI), Nuvei — née Pivotal — operates in the payment processing space and recognized Benjamin’s skills immediately. Within months, he became a top rep and within a decade, he would climb up the ladder to become vice-president.

His work was so appreciated that the company even supported his musical aspirations by letting him go on tour for up to a month at a time, then allowing him to resume his duties. It was a formative experience and he grew with the company all while building his innate sales and artistic skills.

Building Sales Systems

Armed with a bachelor's degree in business management and a growing list of responsibilities as sales manager and later VP, Benjamin had the opportunity to make a significant career change, after such a lengthy and fulfilling run. Interested in empathetic sales tech, he looked to the Software-as-a-Solution (SaaS) sector for his next challenge.

“I was looking for a lively organization,” he said. “Something exciting in a completely different industry that embraced a tech culture environment.”

The company, which specialized in security software and workforce management, was a great fit. Benjamin dove right in immediately, overseeing everything from onboarding to best practices.

“I was recognized within the organization for my capacity to improve on upgradability, the team, its structure and also enablement. So they actually created a role for me, as a Director of Revenue Operations and Enablement, to help out not only with sales, but also client success, marketing and all things revenue. And in doing so, I helped accelerate growth while planting seeds for more sustainable growth.”

Meaningful Connections

Though his love of music and performance will never fade, Benjamin’s passion for sales and interacting with clients gave him a new purpose.

“I was always really interested in psychology and sociology,” he said. “Even in high school, you could find me reading a university-level psychology textbook at lunch time. For me, dealing with human beings is always interesting. It's all about human interactions, how you communicate with people and, ultimately, how to improve the lives of others while contributing to the success of an organization that you believe in.”

This empathy-first approach is not so popular in certain fintech circles but Benjamin continues to go against the current.

“Listening is never a bad idea. I helped sales professionals who were taught the wrong way and worked with sales teams to understand the value of compassion. When you can shift people’s perspective this way, they come to realize that the process is more than just closing a deal.”

A Natural Fit at ClearEstate

Benjamin’s unique, empathy-first approach to sales and marketing left little room for doubt when ClearEstate approached him to join their growing team.

“What sold me was how their vision for growth is absolutely transformational,” he said. “There are fascinating and diverse revenue streams, but it’s also a perfect place for somebody like me that enjoys thinking creatively and solving complex problems in these very sensitive, human situations.”

Since joining ClearEstate this fall, Benjamin has been spending much of his free time researching the bereavement space and says he is not afraid of the complexity involved with the material.

“I have experience in dealing with sensitive or serious situations. Transactions, and now estates: the two are very closely connected. The most stressful moments in our lives are the result of money and/or death. I want our sales approach to be helpful and our content to be meaningful. For that we must make efforts to understand why people come to us and how we can help them most effectively. Human considerations come before the transaction itself, and there’s no other way I’d rather do it.”

Benjamin Bergeron-Osajie can be reached at