Head of Sales

NYC (In-Office, 5 Days/Week)

Top of market pay

60+ Hours/Week

Fastest-Growing AI-Native PropTech Company in the World

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.

Demand for Henry is growing faster than our sales team can keep up with. That means more AEs, more BDRs, and new segments to cover.

Today our CEO manages the sales team on top of running the company. That got us here, and it won't get us to the next stage. We need a full-time leader to coach the team, set the strategy, fine-tune what's working, and scale it fast.

• Hitting the number. Leadership sets the revenue target. You own the plan to hit it, the forecast, and the week-to-week execution that gets us there.

• Who we target. Decide which customers we go after and how we segment them, by firm size, deal type, and buyer, so every rep knows exactly where to spend their time.

• The team. Lead, coach, and grow our AEs and BDRs. Run the weekly rhythm of pipeline reviews, deal reviews, and 1:1s. Build onboarding and training that gets new reps ramped fast.

• Hiring. Build the plan for every new sales seat, set the bar, and help close the reps you want.

• Comp and quotas. Set quotas for every rep and help shape a commission plan that rewards the right behavior.

• The sales motion. Define how we sell to each segment, from individual brokers to the largest firms: stages, qualification, pricing, and a clean handoff to Account Management for renewals and expansion.

• Pipeline health. Work with marketing and the BDR team to make sure the top of the funnel is full of the right accounts.

• Getting in the deals. Jump into the biggest opportunities, help reps get unstuck, and close alongside them.

• Tools and data. Keep the CRM clean, the reporting honest, and the forecast one you'd bet on.

• Co-piloting with the founder. You report directly to the CEO. He'll stay close on strategic accounts, and you'll own the team and the day-to-day, pulling him in at the right moments.

• 5+ years of sales leadership experience at a fast growing Series A-C startup

• Scaled revenue from mid single single digits to mid double digits as the number 1 or 2 in the sales org

• You've led a team of AEs and BDRs at a high-growth SaaS or AI company, carried a team number, and hit it. You can walk us through exactly how.

• You've scaled a sales team through fast growth, including hiring, onboarding, and building the process as you go.

• A player-coach. You're as comfortable on a live deal as you are running a pipeline review.

• A builder. You won't inherit a playbook. You'll write the one we use.

• Commercially sharp. You know what makes a deal real and what makes a forecast wrong.

• 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.

• Have sold to CRE, capital markets, or financial services

• Have built a sales team from early stage at a Series A to C startup

• Have led both enterprise and high-velocity sales motions

• A real team, a product customers already love, and a category-defining company to build

• The fastest path to VP of Sales or CRO at a company that will need one

• Equity in a venture-backed company growing faster than we can staff

• A founder who will fight alongside you and get out of your way once you're rolling