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Sherwood & Company · Careers

Careers.

Motivated to help the motivated.

Talk to Blake See what you get

Join The Team

Built for agents who
take this seriously.

Sherwood & Company is a RealTrends Verified team serving Greater Boston and the North Shore — full-time, hands-on, and built around real mentorship instead of a desk and a good-luck.

We're deliberately boutique — large enough to offer full support, small enough to stay personal and thoughtful. Real estate is a service profession first: clear, steady communication supports confident decisions, and long-term relationships matter more than short-term transactions.

That means real training from a team that does this work full-time, a referral-driven business built over years across Greater Boston and the North Shore, and colleagues who collaborate rather than compete.

2010
Where it began
2022
Sherwood & Company founded
6
Team members
5
Languages spoken

RealTrends Verified · Compass Massachusetts, LLC · Greater Boston & the North Shore

Why Join Us

What you get when
you join.

A full-time team, real support, and technology and marketing usually reserved for the top of the industry.

Compass Tools & Marketing

Build on the #1 U.S. brokerage's platform — an in-house marketing and design studio, Private Exclusive and Coming Soon listings, and technology that puts you in front of the right buyers and sellers.

Real Training, Not a Desk

Learn the business from a team that does it full-time — pricing, negotiation, and lead generation — with hands-on guidance from day one, not a binder and a good-luck.

A Team That Refers

Tap into the Nor'Easters Networking Community and a roster of repeat clients and referral partners built over years across Greater Boston and the North Shore.

Tools We Built Ourselves

Use PropPrompt, our in-house real-estate technology, to sharpen client analysis and market strategy — an edge most agents simply don't have.

Give Back

Through the Sherwood & Company Charitable Foundation, the team invests in the communities we serve — because the work is about more than the transaction.

Motivated to Help the Motivated

We're a RealTrends Verified team that takes the work — and each other — seriously. If you're driven and genuinely care about people, you'll fit right in.

Blake Sherwood and Roei Biberstain on the front steps of a Back Bay brownstone.
Culture
A team that shows up for each other, not just for clients.

Our Story

Built with intention,
not by accident.

Every role on this team exists on purpose. Here's how it came together.

2010
Where It Began

Blake Sherwood starts his real estate career at Vanguard Realty, building a practice on relationships, consistency, and hands-on service.

2018
A New Chapter with Compass

Blake joins Compass as one of the earliest agents in Boston — Agent #122 in the city, #2,100 nationally — and begins mentoring newer agents.

2020
The Turning Point

The pandemic makes it undeniable: exceptional service requires focus, and focus requires delegation. That clarity shapes the team to come.

2022
Sherwood & Company Forms

The team launches — Roei as agent partner and Athina as Operations Coordinator, soon joined by Rick and John. Each role is intentional; each person is part of the whole.

“We are not building the biggest team — just a strong, values-aligned, well-supported one.” Blake Sherwood · Sherwood & Company

Ready to talk?

Let's start the
conversation.

Tell us about yourself and where you want to take your career. Every conversation is confidential, and there's no pressure — just a real look at whether this is the right fit for both of us.

Call 617.833.0036 Email Blake

Blake Sherwood · Vice President, Team Lead · Sherwood & Company at Compass

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