Erin DiCarlo has seen the same situation play out hundreds of times — older adults transition out of their homes and encounter frustration, uncertainty and communication breakdowns. An emotional season becomes stressful, taxing and complicated.
It was while meeting people at this pain point that she started Dovetail Companies, a real estate brand that specializes in supporting seniors through the planning, moving and home-selling process.
“I had an ah-ha moment,” she told Boston Agent magazine. “What if I created a one-point-of-contact business where we did it all. The families just dealt with one warm expert human, and we had care management, move management, real estate and all those services in-house. Then, they could focus on the emotional aspects of this while we handled all the logistics.”
Beginning by helping seniors answer questions like, “Where should we live?” and “What’s best for my situation?” DiCarlo creates personalized plans that make sense for each client using her signature “move first, sell later” approach. Along the way, she connects clients to the experts they need, from estate-planning specialists to donation coordinators to mental health professionals.
DiCarlo’s grandparents inspired her career journey. At 21, she lost her grandmother and watched her grandfather with Alzheimer’s enter an assisted-living facility. She became a hospice volunteer and gained experience as a dementia practitioner and geriatric care manager, learning the intricacies of senior living from the inside out.
“I know I was put on this planet to help seniors live a better life,” she said. Beyond her work at Dovetail, DiCarlo has mobilized other agents to meet the unique needs of older adult clients. She’s created proprietary training programs and helped launch Compass Plus.
“Creating a real estate practice to meet the needs of older Americans is smart business,” she pointed out. Over four million Americans will turn 65 in 2026, meaning 11,200 people will hit retirement age daily this year. “This demographic is looking for expert guidance and is willing to pay a premium price to access it,” DiCarlo said.
What’s the key to her business model? Education, respect and an open ear, she explained. DiCarlo pushes back against an industry that values hustle and rushes the home-selling process. “Work with seniors, not around them,” she said. DiCarlo always meets with her senior clients one-on-one before involving family members, clarifying their needs and goals in a respectful, calm setting.
To other agents, DiCarlo advised, “Slow down. Get into alignment, make a good plan, involve the client, and ultimately you will sell quicker. When we prioritize the client’s needs, the pieces of the process fall into place.”