Real Estate Growth Associate

Real Estate Growth Associate (0-2 YOE)

Cypress Pathways | Boston, MA (Hybrid) | Part-Time

About Cypress Pathways

Cypress Pathways (cypresspathways.com) is a real estate advisory firm built on entitlement, permitting, and brokerage expertise across New England, with a focus on Greater Boston. Our pitch is simple: before a client spends real money assembling a development team, we tell them — honestly — whether their site or project is worth pursuing, and what it will take to get it approved.

We're a small, high-trust team. Our Founder drives lead generation, brand, and business strategy. Our Co-Founder brings urban planning expertise and shapes how we position our work in the field. We work across three service lines:

• Site Sourcing — identifying viable development sites using our knowledge of zoning and market comps.
• Due Diligence — packaging a client's development possibilities and permitting pathway into a clear, actionable report.
• Technical Assistance — hands-on support through funding applications, government meetings, stakeholder engagement, and the permitting process itself.

The Opportunity

Cypress Pathways is at an inflection point. We're growing, with client leads in motion and completed or in-flight engagements across Massachusetts and Rhode Island. Now, we're looking to build a real pipeline and sales process with a partner who thinks about growth seriously.

This is a partner-track role with the potential for long-term upside. We’re looking for someone who will help us build and run our sales playbook. If you want to build the growth engine of a small, mission-driven real estate advisory firm and earn a real ownership stake in the outcome, we want to talk to you.

What You'll Do

• Build and run our pipeline. Attend industry events, make introductions, cold call, and cultivate referral relationships — this is hands-on business development, not oversight of someone else doing it.
• Build a referral network. We're especially interested in candidates who can build relationships among developers, landowners, general contractors, architects, and environmental engineers — the people who see opportunities before they hit the open market.
• Own our CRM and sales process. We currently track leads in a spreadsheet. We need someone to design and run a real system — pipeline stages, follow-up cadence, conversion tracking — and hold us accountable to using it.
• Help shape our go-to-market strategy. You'll have real input on pricing conversations, which client segments to prioritize, and how we position our three service lines. We want opinions, not just execution.
• Support deliverables when useful. This isn't the core of the role, but real estate and permitting fluency is a plus — occasionally you may help shape a due diligence packet or sit in on a technical assistance engagement.
• Travel around Massachusetts periodically (roughly once a month, on average) for client meetings and site visits.

What We're Looking For

• Located in or around Greater Boston. This is a non-negotiable for us; physical proximity to our market is a key component of this role.
• 0-2 years of experience in real estate sales, brokerage, or business development. We’re interested in your internship, professional experiences, or hobbies that might contribute to your experience.
• Exposure to Massachusetts real estate — developers, landowners, brokers, GCs, architects, or environmental engineers. 
• A self-starter who's comfortable building from scratch. We don't have a plug-and-play system. You'll help create it.
• Genuine interest in what we build, not just in closing deals. We work on projects that shape the urban landscape, and we want someone who's motivated by that — not a "close at all costs" mentality.
• A proven track record in a sales or business development environment. We're open on what that looks like specifically — we're curious to see what you bring.
• Boston-based or nearby, and comfortable traveling within the state as needed.
• Planning or permitting knowledge is a nice-to-have, not a requirement. Real estate and sales instincts matter more here.

Compensation & Path to Partnership

Compensation for this role will include a mixture of commission on closed deals, revenue split for billable work, and part equity ownership. Exceptional performance could lead to larger equity share.

Time commitment is expected to be part-time to begin with the potential to scale into a full-time role.

What Success Looks Like

By the end of year one, we'd consider this role a clear success if we've landed 2–3 smaller Technical Assistance clients (phased consulting engagements) and one larger anchor client on a bigger hourly TA / project management engagement. Along the way, we'll also be watching softer indicators: growth in weekly qualified leads, and improvement in how many of those leads convert to paid work compared to where we are today.

What Matters Most to Us

Closing ability matters, but it's not the whole picture. We're looking for someone who cares about the why behind the deals we take on — the projects, the neighborhoods, the impact — and who's genuinely excited by the idea of helping build something from the ground up, not just closing what's already in front of them.

How to Apply

Please email your resume and a brief cover letter to info@cypresspathways.com with the subject line “Cypress Pathways Associate Application.”