Compass, Community, and Capital: Jennifer Ohlman’s Playbook for Growth

In this conversation, Jennifer Ohlman, Strategic Growth Manager at Compass in Southwest Florida, walks us through her path from big-firm consulting to startups, property management, and ultimately agent growth and brokerage partnerships. She covers what Compass offers agents (supportive tech, local culture, and community impact), how she evaluates fit, and what she’s seeing across Naples and beyond—from spec-home lifestyle design to fast-rising neighborhoods. Jennifer gets candid about career inflection points: bootstrapping a short-term rental business, navigating COVID shutdowns by partnering under existing vendors, and learning to “lead from behind” with clear communication and public kudos. She also shares her go-to books and podcasts, her daily routine built around fitness and networking, and how she builds passive income through buy-and-hold real estate. We wrap with what’s next at Compass (AI tools to reduce agent busywork) and Jennifer’s personal travel plans.

 

 

---------------------------------------------------------- Be a Guest: Are you a successful Naples-area business owner, entrepreneur, or professional with insights to share? Apply to be a guest at Driven: Unscripted Success and share your expertise with a wide audience eager to learn about you.