Director of Enterprise, Brokerage

Henry AI, Inc.; New York (NY); On-site; USD 180,000 - 260,000; Full time

Benefits offered by this job

Salary + equity

Health, dental & vision

Wellness stipend

Generous PTO

Catered meals daily

Beautiful SoHo office

Early-stage impact

Job summary

Henry AI, Inc. is a NYC-based startup bringing AI to the commercial real estate industry.

We are seeking a senior operator who can own end-to-end brokerage deals, from first meeting through contract, while building relationships with top CRE firms and guiding product feedback from the field. You will work directly with founders, own strategic initiatives, and shape the enterprise sales playbook, with a heavy in-person presence at our SoHo/Manhattan office.

Qualifications

• 5+ years working directly for a CRE brokerage.
• Deep relationships across brokerage leadership at top firms.
• Knowledge of pitches, BOVs, offering memoranda, comps and underwriting.
• Ability to run a deal end-to-end from first meeting to signed contract.
• Founder-level ownership; drive custom proposals and partner calls.
• Located in NYC or willing to relocate for in-person 5 days/week.
• Willing to work 60+ hours per week.
• Bonus points for closing enterprise software deals with brokerages or financial services; experience across top brokerages; startup experience (Series A–C).

Responsibilities

• Own a named list of the largest CRE brokerages and drive firm-wide adoption.
• Take every deal from first meeting to signed contract: discovery, pilot, pricing, legal, security review, procurement.
• Design the proof of concept and scope the rollout with clear success criteria.
• Work with brokerage leadership and top-producing brokers; be credible in every room.
• Translate brokerage feedback into requirements for the product team.
• Co-pilot with the founder; lead strategy and involve the CEO when needed.
• Build the enterprise playbook to land additional brokerages after these.

Job description

Location: In-office, 5 days a week at our SoHo office in New York City. We believe great things happen when we build side by side.

Who We Are

Henry is bringing AI to one of the world’s largest and least digitized industries: commercial real estate. We help brokers work faster, win more deals, and drop the busywork. We are Series A, venture-backed, New York-based, and hiring people who want to build what comes next.

Responsibilities

• The brokerages that matter most: Own a named list of the largest CRE brokerages and the path to firm-wide adoption at each one.

• Deals, end to end: Take every deal from first meeting to signed contract: discovery, pilot, pricing, legal, security review, and procurement. You run every step yourself.

• The pilot and the scope: Design the proof of concept, agree with the customer on what success looks like, and scope the rollout. There’s no handoff to a solutions team.

• Senior relationships: Work with brokerage leadership, heads of capital markets and investment sales, top-producing brokers, and the teams that support them. You’re credible in every room because you’ve sat in their seat.

• The voice of the brokerage customer: You know how brokerage deals actually get done, and you turn that into clear feedback for our product team.

• Co-piloting with the founder: The CEO will stay close on the biggest accounts until trust is built. You own the strategy and pull him in at the right moments.

• The enterprise playbook: You won’t inherit a process. You’ll build the one we use to land the next ten brokerages after these.

How We Assess

• Required: 5+ years working directly for a CRE brokerage

• Deep relationships across brokerage. You know the people who lead teams and run the business at the top firms, and they take your call.

• You know the workflow cold: pitches, BOVs, offering memoranda, comps, underwriting, and what it takes to win a listing

• You can run a deal end to end, from the first conversation through pilot, scope, and signed contract, without someone holding your hand

• Founder-level ownership: No task is “in someone else’s lane.” If something needs to happen, like a custom proposal, a partner call, or a 10pm redline, you make it happen.

• A massive chip on your shoulder: You’ve been overlooked, doubted, or counted out. You have something to prove, and no one is going to stop you.

• You’re in NYC or willing to relocate (in-person, 5 days a week)

• You’re ready to work 60+ hours a week because you’re hungry, not because someone’s watching the clock

• Bonus points if you: have closed enterprise software deals, especially into brokerages or financial services; have worked across more than one of the top brokerages; or have worked at a Series A–C startup

What We Offer

• Competitive salary + equity: A top-of-market base and meaningful stock options, so you share in what we build

• Health, dental & vision: Comprehensive coverage for you and your family

• Health & wellness stipend: Stay sharp with access to Equinox gyms, on us

• Generous PTO: Take the time you need to recharge, plus company holidays

• Breakfast, lunch & dinner: Catered meals in the office, every day

• Beautiful SoHo office: Work from a bright, inspiring space in the heart of Manhattan

• Early-stage impact: Work directly with the founders, own real problems, and help shape the company from the ground up

Please note that Henry AI may use AI notetakers and other recording devices in the recruiting process. If you interview with us, with your consent, we may record your conversations and summarize them into notes for internal use. Recording is optional, and declining will not affect your candidacy.

Henry AI is an equal opportunity employer. We are committed to diversity and inclusion in our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.