Greg Tomlin – Owner & Principal at Pineapple Insurance, brings a fresh, entrepreneurial approach to the insurance industry:
- Built a successful 9-year career at Dell Technologies, leading territory expansion across the U.S. and secured partnerships with large enterprise clients as well as AI Cloud Service Providers.
- Specializes in using technology and customer-centric strategies, with a vision to modernize traditional insurance experiences.
- Focused on building Pineapple Insurance into a community-first, agent-powered brokerage that puts simplicity and service at the center of every client interaction.
- Passionate about delivering a world-class, locally focused experience across all personal lines of insurance — blending enterprise-level execution with hometown service.
I’m a proud Tampa native and passionate about supporting our local community — whether it’s through volunteering, sponsoring community events, or mentoring young professionals looking to grow their careers. Outside of work, you’ll often find me paddleboarding Florida’s beautiful waterways, exploring local markets, or spending time outdoors with my family