In 2016, the Southwest Florida Community Foundation launched a transformative impact investment centered on the renovation of the historic 1924 Atlantic Coast Line Railroad Depot in Fort Myers. Jon Romine, who was a principal at EnSite, Inc., led the urban planning, landscape architecture, and civil engineering efforts for the 2.7-acre LEED Gold-certified campus, which is now known as Collaboratory. As a Foundation board member, Jon also served as the in-kind owner’s representative and project manager for the former President and CEO of Collaboratory, Sarah Owen, bringing his expertise in financial oversight, stakeholder engagement, and project leadership to the forefront.
Thanks to Jon’s strategic guidance, the project was completed ahead of schedule and under budget. He successfully coordinated a complex web of public and private partners, including the City of Fort Myers and New Market Tax Credit investors, while maintaining alignment across civic, philanthropic, and regulatory priorities. His ability to navigate high-stakes negotiations, manage capital project finances, and lead cross-sector teams was instrumental in transforming the newly vacant train depot into a thriving hub for regional collaboration.
The project’s success was made possible in part to Jon’s concurrent efforts to privatize the Imaginarium Science Center and the Southwest Florida History Museum, unlocking the historic depot for adaptive reuse and long-term community value.
In 2021, the Southwest Florida Community Foundation launched an audacious mission: To eliminate the region’s most persistent social problems by the year 2040. Recognizing that no single entity can solve complex issues alone, this bold commitment embraced a systems-level, cross-sector approach grounded in community, shared accountability, and servant leadership.
To bring this vision to life, President & CEO Sarah Owen tapped Jon Romine to co-architect the strategic roadmap. With a reputation for navigating complexity and aligning diverse stakeholders, Jon co-led the development of a bold, data-informed roadmap that integrated multiple issue areas including housing, education and workforce, immigration, the natural and built environments, health and wellness, and arts and culture.
Jon’s strategic leadership extended beyond planning. He designed and implemented a capacity-building training program to equip organizations and community members with the tools and language needed for effective collaboration. He also facilitated the realignment of existing funding streams to accelerate early wins and support coordinated action.
As a result, the project that is now known as Collaboratory, has evolved into a living digital dashboard that enables cross-sector partners to track progress, align efforts, and drive measurable outcomes. Under Jon’s guidance, the strategy attracted nearly $50 million in new investment to Southwest Florida and laid the foundation for a more resilient, equitable, and connected region.
This work highlights Jon’s strengths in systems thinking, financial stewardship, strategic facilitation, cross-sector alignment, and community-centered design—skills that continue to shape transformational outcomes across the region.
Jon’s groundbreaking work at Collaboratory is what inspired him to launch Viriditas, which provides fractional, campaign-based, or project-based executive leadership with the expertise and dedication to drive lasting impact by turning ideas into measurable action for businesses, nonprofit organizations and community leaders.
