Charlie Reinkemeyer: Associate at PeakSpan

Charlie Reinkemeyer

Associate

In their words:

For the majority of my life, I was dead set on becoming a football coach. However, I quickly came to realize that being a growth-stage software investor, specifically at PeakSpan, or a coach, are fundamentally similar. As a partner of choice, it is my responsibility, and privilege, to work vigorously alongside talented entrepreneurs and help put them in the best position to succeed, just as any coach would do. In that capacity, I currently sit as a Board Observer at Tapcheck, Nectar, Arist, Opkey, and Letterhead, and enjoy every second of it.

Sector Expertise

Investments

About:

Charlie joined PeakSpan in 2022 after graduating from Middlebury College, where he studied Political Science and Psychology and played on the football team. Before Middlebury, he played football in the Big Ten for the University of Illinois Fighting Illini. Outside of work, Charlie enjoys all things sports (playing, watching, and talking), and listening to country music.

What makes you excited to come to work each day at this stage of your career?

What excites me most at this stage of my career is being in the trenches with great people, working on solving problems that matter. I’m energized by earning trust with founders and helping them navigate moments that meaningfully shape their companies, whether that’s refining a go-to-market motion, pressure-testing a hire, or simply being a thought partner when things feel uncertain.

What’s a project or moment at PeakSpan where your involvement changed a company’s trajectory?

Identifying a new product area for our Portfolio Partner, Nectar, and helping them think through how to deliver it in a way that drives higher customer satisfaction while also generating incremental revenue. At PeakSpan, we have the advantage of being deeply steeped in specific B2B software sectors, with a strong understanding of category trends and underlying market dynamics. That perspective allows us to identify opportunities companies may not always see from the inside. Enabling our portfolio companies to leverage that insight is core to how we add value, and it is something Nectar has meaningfully capitalized on as a result.

Why was PeakSpan the right place for you to do your best work?

PeakSpan provides an environment where employees are encouraged to think creatively and act with real agency while still operating within a highly collaborative culture. Individuals are trusted to form independent points of view, take ownership of their work, and push ideas forward, but those ideas are continuously sharpened through open dialogue and collective discussion. The expectation is not to be right in isolation, but to arrive at the best answer together. That balance of autonomy and collaboration creates a culture where people are empowered to do their best work and where outcomes are consistently stronger as a result.

At the end of a multi-year partnership, what do you hope founders say you were known for?

There is a scoreboard for every company: the value at which it ultimately exits. That number matters — and it always will. But I hope it is never the first thing mentioned when an entrepreneur talks about working with me. Not because it’s unimportant, but because this is, at its core, a people business. I hope founders say that Charlie Reinkemeyer helped me reach my full potential as an entrepreneur; that he helped me lead with clarity and empathy, was a steady partner through thick and thin, and pushed me to be a servant leader. Someone who invested in others, built trust across our organization, and enabled people to do the best work of their careers. In the end, the value we achieved together was secondary. The more meaningful impact was the value he helped me create with the people around me, that ultimately led to the outcome on the scoreboard.

Personal side: