VP, Real Estate Development & Finance

Tower Hill Insurance Group has an exciting opportunity for a talented VP of Real Estate Development & Finance who enjoys intellectual challenges and is seeking a rewarding career with a company that is experiencing growth. Not only is Tower Hill Insurance one of Florida's most trusted names in homeowners insurance, but it offers great opportunities for career advancement and personal growth, along with very competitive benefits and rewards.

We are growing at a consistent pace and seek professional individuals with drive, team mentality, who want to make an impact, and are committed to a long‑term career in the insurance industry.

The Vice President of Real Estate Development & Finance is responsible for overseeing large-scale land development projects in Florida and Kentucky, including a 300‑acre property in Alachua, Florida—home to a newly constructed 63,000 sq. ft. office building—with plans for a golf course, multi‑family communities, single‑family neighborhoods, and mixed‑use commercial property. This position plays a pivotal role in turning long‑term vision into fully realized, sustainable communities.

This role requires deep experience in building communities from the ground up, strong financial acumen, and a proven track record securing non‑recourse financing and other capital structures for major development projects.

• Lead master planning and execution of multi‑phase developments across Florida and Kentucky.
• Serve as the primary development and finance executive for the Office of the CEO’s real estate initiatives.
• Create and manage strategic plans, development timelines, and long‑term vision for each property.
• Oversee end‑to‑end development of new communities, including single‑family neighborhoods, multi‑family projects, mixed‑use commercial spaces, and amenities such as golf courses and recreational facilities.
• Work closely with civil engineers, architects, land planners, and contractors to bring master‑planned communities to life.
• Identify, structure, and secure non‑recourse loans, construction financing, and long‑term capital for all phases of development.
• Build relationships with banks, private lenders, and institutional financing partners.
• Develop proformas, financial models, and return analyses for each project phase.
• Oversee site preparation, infrastructure development, entitlements, permitting, and compliance.
• Manage contracts, budgets, and project schedules to ensure high‑quality, on‑time delivery.
• Work with local governments, planning boards, and regulatory agencies in Florida and Kentucky.
• Establish and grow a high‑performing development team within the newly created entity.
• Collaborate closely with Office of the CEO leadership to ensure alignment with long‑term portfolio goals.

This job description reflects the general duties considered necessary to describe the essential functions of the job and should not be considered a complete description of all the work requirements and expectations of the position. Tower Hill reserves the right to assign duties not listed herein as necessary to accomplish the goals of the organization.

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Bachelor’s Degree in Real Estate, Finance, Business, Construction Management, or related field required. Master’s Degree in Business Administration, Real Estate, or related field preferred.

Minimum of ten (10) to fifteen (15) years of work experience in real estate development, land development, and real estate finance required, including:

• Demonstrated experience developing communities from raw land through full build‑out,
• Proven success securing non‑recourse financing and complex capital stacks,
• Expertise in mixed‑use, residential, and commercial development,
• Strong knowledge of zoning, entitlements, permitting, and regional regulations in Florida. Experience in…