Building a Sales Career that Matters: Aaron Michalowski’s Rapid Growth at EvenUp
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Aaron Michalowski wasn’t looking for just another paycheck in his last job search. His background in psychology and drive to make a difference spurred him to pursue a career aligned with his values.

“Helping plaintiffs who’ve been lowballed and pushed aside—leveling that playing field—that’s where I wanted to be,” says Aaron.

A chance encounter with EvenUp co-founder and COO Ray Mieszaniec intrigued him enough to learn more. Now, as a Senior Account Executive at EvenUp, Aaron is proud to champion a company that’s improving the lives of personal injury plaintiffs by empowering their counsel to seek fair settlements from insurance companies.

Aaron’s Rise from SDR to Senior AE in two years

Aaron joined EvenUp two years ago as one of the founding Sales Development Representatives (SDR), and his career trajectory has been nothing short of remarkable. After a promotion to Account Executive in his first year, he’s been promoted again and is thriving as a Senior Account Executive.

Beyond his rapid career growth, Aaron values the freedom to tailor his sales approach. 

“There’s a script when you start,” he explains, “but as you grow comfortable, you discover what works for you, experiment, and share ideas with the team.” 

This culture of trust has empowered Aaron to innovate, even suggesting a shift from traditional end-of-quarter sales blitzes to a proactive, client-focused approach. 

“It’s all about building genuine connections,” he says.

Collaboration is the backbone of sales at EvenUp

Aaron says collaboration isn’t just a buzzword at EvenUp—it’s the backbone of the company’s culture and success. He works closely with the customer success team to ensure clients feel supported long after they’ve signed on. 

“Our job doesn’t end once the prospect becomes a customer. We’re here to make sure they’re happy every step of the way,” Aaron emphasizes.

This intentional, client-centered mindset defines EvenUp’s sales culture. “We’re gritty but in the most mindful way possible. We’re not just going through the motions—we’re genuinely connected to our clients. Everything we do is to benefit them.”

Aligning personal values with EvenUp’s expanding capabilities

Aaron feels deeply aligned with EvenUp’s mission and the products he represents. His favorite new product is the Settlement Repository, which he describes as an invaluable tool for personal injury lawyers to search through their past settlements to bolster negotiations. He’s equally enthusiastic about the new Executive Analytics tool, which he believes will empower law firms to excel by leveraging actionable data insights.

For an account executive, Aaron is uniquely close to product development. He collaborates directly with the product team to share client feedback and shape the roadmap, ensuring new tools address the real-world needs of personal injury lawyers. This hands-on involvement reinforces his commitment to EvenUp’s mission and its transformative impact on law firms.

Work-life balance to thrive professionally and personally

As a fully remote employee, Aaron has found the freedom to balance his professional and personal life seamlessly.

“There’s no micromanaging here. EvenUp trusts us to do our work well and gives us the freedom to live our lives,” Aaron says. 

This trust fuels his ability to perform at a high level while maintaining a healthy work-life balance.

Aaron’s journey at EvenUp highlights the company’s commitment to fostering employee growth while delivering client-centered innovation. For those looking to build a career in legal tech, Aaron’s story underscores the unique opportunities EvenUp offers to make an impact while growing professionally.

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