From military service to real estate leadership
My full career history, matching my LinkedIn profile. Select any role for details.
Raised in a real estate family
My father was a homebuilder, my mother was a real estate broker and my uncle was a mortgage lender. I learned early how construction, sales and financing depend on each other, and that understanding still shapes how I lead.
Firefighter
Firefighter and emergency services specialist with the 439th Civil Engineer Squadron at Westover Air Reserve Base. I responded to aircraft, structural and medical emergencies, operated firefighting and rescue equipment, and trained in aircraft fire suppression, structural firefighting, hazardous materials and emergency rescue.
- Responded to aircraft and structural fire emergencies, protecting personnel and critical assets.
- Led training drills and cross-training that improved unit readiness.
- Earned DoD Firefighter I and II, Airport Firefighter and HazMat Awareness and Operations certifications.
21E Heavy Equipment Engineer Operator
Moved from the Air Force to the Army through the Blue to Green program. I operated and maintained bulldozers, graders, excavators and loaders to build roads, airfield runways, ammunition storage areas and defensive positions, and trained junior soldiers in safe operation and maintenance. Retired honorably in August 2009.
- Built and maintained roads, tank trails, airstrips and protective berms supporting mission success.
- Achieved 100% equipment readiness through preventive maintenance and timely repairs.
- Led small teams operating heavy equipment in austere conditions.
Team Leader
Built and led the Winslow Homes sales team. I mentored agents, developed sales strategies and ran daily operations while guiding buyers and sellers through every step of the transaction.
- Built one of the leading foreclosure and distressed property listing operations in New England.
- Represented luxury properties valued above $10 million.
- Voted Best of Central MA for many consecutive years.
Founder, Managing Partner and President of Sales and Operations
I founded Winslow Homes and built it into a multi-state brokerage and homebuilding firm. I set the strategic vision, oversee real estate sales, new home construction, land development, site work and mortgage lending, and serve as managing broker. I manage profit and loss, budgets and schedules, negotiate land acquisitions, secure permits and build partnerships with lenders, architects, engineers and subcontractors.
- Grew annual sales volume to more than $200 million and expanded into four states.
- Personally sold more than 3,000 homes and over $1 billion in career volume.
- Led approximately 100 agents across multiple states and increased sales 150%.
- Implemented CRM and AI-powered marketing to target buyers, optimize pricing and generate leads.
Bachelor of Business Administration
Earned my degree with military honors while running the business full time. I am now pursuing my Master of Business Administration.
Managing Broker
Lead Massachusetts sales operations, contract negotiations and regulatory compliance. I provide market analysis and negotiation expertise and mentor agents. Licensed in Massachusetts since 2009.
- Expanded brokerage and new home sales across Massachusetts and New England.
- Built training and compliance programs aligned with Massachusetts real estate law.
- Used AI-enabled CRM tools to improve pricing, marketing and lead conversion.
Licensed Hoisting Engineer (1A, 2C)
Operate and manage cranes, excavators, bulldozers and heavy equipment for residential construction and land development, including excavation, grading, site preparation and winter snow removal.
- Completed complex excavations and foundations for custom homes and multi-lot developments with zero safety incidents.
- Cut equipment downtime 25% through preventive maintenance and safety training.
- Improved grading accuracy with GPS-enabled equipment and digital site plans.
Licensed Construction Supervisor
Manage residential and land development projects from site preparation through final occupancy, including design, permitting, inspections, budgets, schedules and subcontractors.
- Delivered new homes and community projects with zero safety incidents and on-time completion.
- Reduced permitting and inspection approval timelines by 20%.
- Built vendor and trade partnerships that supported expansion across Massachusetts.
Certified General Contractor
Oversee new home construction, remodels and land development in Florida from pre-construction planning to final walkthrough, including design, engineering, permitting, procurement, subcontractors, budgets, schedules and safety.
- Built vendor and subcontractor networks across Florida that support rapid scaling.
- Aligned construction schedules and financing programs with sales and mortgage teams.
Managing Broker
Lead Florida sales operations, client transactions and regulatory compliance, and mentor agents across a multi-state portfolio.
- Drove significant growth in home sales in Florida and the Southeast.
- Streamlined contract management, permitting and inspections to shorten timelines.
- Expanded market share with data-driven and AI-powered marketing.
Managing Broker, Connecticut and Rhode Island
Oversee licensed agents, sales operations, contract negotiations and compliance in both states while coordinating with construction and lending teams.
- Closed residential and new home transactions with 100% client satisfaction.
- Implemented compliance processes and digital transaction systems that reduced risk and timelines.
- Delivered turnkey solutions with builders, architects and lenders.
Author and Real Estate Training Coach
Founded Winslow Homes Publishing to turn 17 years of experience into practical education for agents, brokers, loan officers, contractors, investors and consumers. The catalog includes Only Sharks: How to Thrive in Real Estate and 190+ live titles.
- Licensing and broker exam prep for all 50 states and Washington, DC.
- Mortgage, investing, construction and consumer education guides.
- Coaching on prospecting, listings, negotiation, lead generation and brokerage growth.
Mortgage Loan Officer
Guided clients from prequalification through closing and designed financing for new construction and purchase transactions.
- Helped hundreds of families secure competitive rates and financing.
- Implemented a digital application workflow that improved approval turnaround.
- Created integrated financing packages with Winslow Homes that raised conversion rates.
Rebuilding after a hurricane
A hurricane destroyed our Florida home. Megan and I kept our family steady, continued serving our clients and kept building our business. In construction, a setback means you clear the site and build again.
Mortgage Banker
Help homebuyers, homeowners, investors and referral partners secure financing from pre-approval through closing, working alongside Megan.
- Conventional, FHA, VA, USDA, jumbo, portfolio and Non-QM lending.
- Financing for self-employed borrowers, investors and veterans.
- Construction and renovation loans with multi-state support.
Leading Winslow Homes across four states
I lead Winslow Homes across Florida, Massachusetts, Rhode Island and Connecticut, directing brokerage, new home construction, remodels, excavation, site work and land development as a Florida Certified General Contractor, Massachusetts Construction Supervisor and Hoisting Engineer. I originate mortgages with The Federal Savings Bank, run Winslow Homes Publishing, coach agents and pursue my MBA while raising our three children, Jaikob, Jaelynn and Julianna. I am ready to bring this full operating experience to an executive team.






