Director of Enterprise, Brokerage
NYC (In-Office, 5 Days/Week)
Top of market pay
60+ Hours/Week
Fastest-Growing AI-Native PropTech Company in the World
About Henry
Henry is the AI deal platform for commercial real estate. Brokers use Henry Deal to run the entire deal workflow: agentic comps, underwriting, and instantly generated deal materials like pitch decks, BOVs, and offering memoranda. We're the fastest-growing AI-native proptech company in the world, backed by tier one VCs including YC. Teams from all of the largest commercial real estate brokerages are on the platform.
Why Now
The largest brokerages in the world represent a huge share of the opportunity in our market. We're already working with teams inside all of them. The next step is turning those teams into firm-wide partnerships.
That takes someone who knows brokerage from the inside. These deals are won on relationships and credibility: knowing how the firm is organized, who the real decision makers are, and how to move a deal across the teams, legal, IT, procurement, and leadership. Our founder has been running these conversations personally. We're now ready to bring on a Director of Enterprise to own them.
What You'll Own
The brokerages that matter most. You'll own a named list of the largest CRE brokerages and the path to firm-wide adoption at each one.
Deals, end to end. First meeting to signed contract: discovery, pilot, pricing, legal, security review, and procurement. You run every step yourself.
The pilot and the scope. You design the proof of concept, agree with the customer on what success looks like, and scope the rollout. No handoff to a solutions team.
Senior relationships. 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.
Who You Are:
5+ years working directly for a CRE brokerage. This one is required.
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, a custom proposal, a partner call, 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/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
Have worked at a Series A to C startup
What You Get
A once-in-a-career shot to make Henry the standard across the largest brokerages in the world
The fastest path to enterprise leadership at a category-defining AI company
Equity in a venture-backed company growing faster than we can staff
A founder who will fight alongside you to win every deal and get out of your way once you're rolling
