Robert Chestnut

Doer
DISC Type : ds

Health Insurance Agent at South Shore Medicare and Health Insurance Advisors

Greater Boston, United States

Overview

Robert Chestnut is a dual-career professional with over 25 years of experience as a Broker Associate at Keller Williams Realty and as a Health Insurance Agent. He specializes in guiding Massachusetts retirees through significant life transitions, including real estate transactions and navigating Medicare. People who have worked with him describe him as professional, dedicated, and top-notch.

Outside of work, Robert is a family man, married with two children, Anthony and Ava. His personal posts suggest he is guided by his faith. He has a varied background, having lived in Hollywood in his twenties before settling in Massachusetts. His interest in Under Armour suggests a potential focus on fitness.

Interesting fact: Before his long-standing career in real estate and insurance in Massachusetts, Robert lived in Hollywood, California during his twenties.

Personality Overview

Fast-paced

Strategic Planner

Long-term Focused

They exhibit a rare combination of being result-oriented but patient at the same time.  Reading between the lines and seeing beyond your words comes naturally to them. They are very professional in their approach and can weigh multiple perspectives together.

Topics They Care About

Real Estate Transitions
With 25+ years of experience, he helps clients with buying, selling, downsizing, and investment properties, focusing on major life changes.
Medicare Guidance
As a health insurance agent, he is passionate about helping Massachusetts seniors understand their Medicare options and avoid common, costly mistakes.
Supporting Retirees
His dual career path is centered around assisting the senior community in Massachusetts with two of their biggest financial decisions: housing and healthcare.

Media Appearances

Robert has no verified media appearances

Work History

4-2025
Health Insurance Agent at South Shore Medicare and Health Insurance Advisors
Broker Associate at Keller Williams Realty
Broker Associate at RE/Max Advanced
Sales Associate at Coldwell Banker Hunneman

Education

Bachelor of Arts from Stonehill College

More Information

Social Presence :

Prographics :

Exp : 1 Location : Greater Boston, United States Job Level : N/A Designation : Health Insurance Agent at South Shore Medicare and Health Insurance Advisors
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Insights For Selling To Robert

During A Call Or A Meeting

DO's

  • Focus on the results that your product produces, expect some strategic questions in return
  • During followups, use phone or text if needed, they should be fine
  • Stick to your standard pitch and qualifying script, don't try to wing it

DONT's

  • Don't focus too much on mutual contacts or bother about other stakeholders, focus on them
  • Don't go over them unless you are left with no other option
  • Don't get into pricing discussions early on, steer conversation towards proven results

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Robert is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Robert

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Robert move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Robert take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Robert

Personality Compatibility


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