Jeff Eckerle’s journey with MESA has come full circle—from startup founder and mentee to dedicated mentor. In this spotlight, Jeff shares insights from both sides of the table and what keeps him committed to growing people through business.
Tell us a little about your background, Jeff.
My path into software started at Deltek, where I spent nearly a decade before co-founding several startups, including Kona (inside Deltek), Capturelife, and SubAssist.
So, I started in a large software company where I learned a lot, but I knew that I was more of an entrepreneurial thinker and wanted to branch out. I’ve worked across different industries and roles—from product innovation to go-to-market strategy and team building—which has shaped me into a generalist who thrives on understanding and impacting all areas of a business.
I’m currently the CEO of Parallax, a venture-backed software company helping professional services organizations manage and forecast their business outcomes more effectively. What excites me now at Parallax is leading a “growth restart” — rebuilding key parts of the team, refining our product and go-to-market strategy, and capitalizing on the opportunities created by AI disruption in the professional services space.
You were a MESA Mentee—tell us about that experience.
I honestly don’t remember exactly how I found MESA—someone must have mentioned it—but I remember thinking, “Wait, someone wants to help me for free?” It seemed too good to be true. But as a first-time entrepreneur without a board or investors, it was exactly what I needed.
MESA provided me with accountability, a consistent rhythm, and someone whose only job was to ask the tough questions that made me better. My first MESA mentor, Brian Olsem, became such a key part of my journey that five years later, I joined a company where he was CEO after Capturelife was sold. That speaks to the strength of the personal network and connection MESA creates.
How long have you been a MESA Mentor, and why did you decide to become one?
I’ve been mentoring through MESA for about three years now. I’ve always enjoyed coaching—whether it was youth baseball or now with entrepreneurs—and I love helping people get where they want to go. I also find it intellectually stimulating to stay close to a business without being in the trenches every day. I’ve mentored one founder consistently during this time and have even connected his company with interns from my network, which created a ripple effect of benefits for everyone involved.
Are there any highlights from your experience working with your MESA Mentee?
Working with Eddie Arpin from OfferingTree has been a real highlight. When we started, he was grappling with tough questions: “Do I raise money? Should I keep bootstrapping?” I didn’t tell him what to do, but through consistent conversations and reflection, he chose to raise venture capital. He went on to close a VC round and scaled his team. Watching him step into a leadership role with new responsibilities and seeing OfferingTree grow has been incredibly rewarding. I feel proud to have been a small part of that journey.
What keeps you involved? What do you get out of being a MESA Mentor?
I genuinely enjoy helping people grow through business—not just growing the business itself but also helping individuals evolve. That’s what excites me most. After years of coaching youth sports, mentoring founders has filled that personal void of guiding others. Plus, staying connected to different kinds of businesses benefits me in my own work. For example, experimenting with AI tools at Parallax and observing how they are applied in other companies provides me with valuable cross-industry insight. It’s a two-way learning experience.
What would you say to others about MESA?
What stood out to me from the beginning—and still does—is the motivation of MESA mentors. There are no strings attached. It’s just people in the Twin Cities who want to share what they’ve learned and help entrepreneurs succeed. That’s rare and incredibly powerful. I think the best thing we can do is share these stories more broadly—have both mentors and mentees talk about the value of MESA. It’s not something MESA can or should promote on its own. It’s up to those of us involved to help spread the word about this unique and impactful community.
