Cassie grew up in New Jersey and is currently based in New York. She graduated Summa Cum Laude from the University of Michigan’s Ross School of Business (Go Blue), where she received her BBA and a minor in Entrepreneurship. Before joining PeakSpan, Cassie worked at multiple startups, which gave her a firsthand view into the challenges and pace of building a company from the ground up. Over the past several years, she has worked closely with founders as an investor, advisor, and board observer. Today, Cassie is a board observer at Routefusion, Boostly, Finally, and Sales Layer.

Being able to partner with incredibly smart and ambitious visionaries who are building forward-thinking products and challenging how businesses operate is deeply energizing to me. I’m constantly inspired by founders and leadership teams who rethink legacy workflows and bet on bold ideas that have the potential to reshape entire industries. I learn something new every day working alongside teams that innovate in pursuit of a bigger vision and are actively changing how the world works.

One of the most meaningful moments at PeakSpan for me was helping a former portfolio company navigate a complex acquisition after three unsuccessful strategic processes. Our team effectively stepped in as in-house bankers, partnering closely with the management team to rebuild the narrative, refine positioning, and run a disciplined process from the ground up. Over the course of nearly a year, I was deeply involved in everything from preparing diligence materials and sharpening the financial story to managing buyer conversations and maintaining momentum through setbacks. Ultimately, the process resulted in a successful transaction and delivered a value-maximizing outcome for the founder under very challenging circumstances.

At the $10–50M ARR stage, one of the biggest mistakes I see is trying to do everything for everyone all at once. Opportunity feels abundant in this phase of company development, so teams chase every use case, segment, and feature request at the expense of focus. That lack of prioritization shows up quickly in bloated roadmaps, unclear go-to-market motions, and teams pulling in different directions. The companies that break through this stage tend to be very deliberate about who they are building for, which problems truly matter, and where they can win decisively. Focus creates clarity across product, sales, and execution, and it’s often the difference between stalled momentum and sustained scale.

Luck favors those who grab it. At PeakSpan, we can't attribute the success of our portfolio companies to pure luck (although a bit of luck doesn't hurt). Instead, we believe success comes from a consistent, disciplined pursuit of excellence by both founders and partners. At the end of a multi-year partnership, I hope founders say we were known for our unwavering commitment, determination, and willingness to do the hard work alongside them.