Head of Sales

Henry AI, Inc.; New York (NY); On-site; USD 180,000 - 290,000; Full time

Benefits offered by this job

Competitive salary + equity

Health, dental & vision

Wellness stipend

Generous PTO

Meals in office

Beautiful SoHo office

Early-stage impact

Job summary

Henry AI, Inc. is seeking a seasoned Sales Leader to coach and scale a high-performing team in NYC. You’ll own the plan to hit revenue targets, forecast, and drive week-to-week execution alongside the CEO.

You’ll define the sales motion, segment targets, and hiring plan while building a repeatable process for AEs and BDRs. This is a founder-backed opportunity to shape a category-defining company.

Qualifications

• 5+ years of sales leadership at a fast-growing Series A–C startup.
• Scaled revenue from mid single digits to mid double digits as the #1 or #2 in the sales org.
• Led a team of AEs and BDRs at a high-growth SaaS or AI company; carried a team number and hit it.
• Scaled a sales team through fast growth, including hiring, onboarding, and building process as you go.
• Player-coach: comfortable on live deals and in pipeline reviews.
• Builder: write and implement our playbook.
• Commercially sharp: understand what makes a deal real and a forecast accurate.
• Massive chip on your shoulder; determined and unstoppable.
• You’re in NYC or willing to relocate (in-person, 5 days a week).
• Willing to work 60+ hours a week due to drive and urgency.
• Bonus: CRE, capital markets, or financial services; building a team early at Series A–C; enterprise and high-velocity sales.

Responsibilities

• Own the revenue plan, forecast, and week-to-week execution to hit targets.
• Define target segments and how we go after them for every rep.
• Lead, coach, and grow AEs and BDRs; establish weekly pipeline reviews and onboarding.
• Plan for new sales seats, set hiring bar, and help close reps.
• Set quotas for reps and shape a commission plan.
• Define the sales motion across segments, stages, pricing, and handoffs to AM for renewals and expansion.
• Maintain a healthy pipeline by coordinating with marketing and BDRs.
• Jump into big opportunities and close deals alongside reps.
• Keep CRM clean, reporting honest, and forecast reliable.
• Report directly to the CEO and partner on strategic accounts; own the team and day-to-day.

Skills

Sales leadership

Forecasting

Pipeline management

Hiring & onboarding

Enterprise SaaS

Team coaching

Playbook development

Deal coaching

Strategic thinking

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. Series A, venture-backed, New York-based, and hiring people who want to build what comes next.

Why This Role

Henry is the AI deal platform for commercial real estate, enabling brokers to manage the entire deal workflow, from agentic comps and underwriting to instant pitch decks, BOVs, and offering memoranda. As the world’s fastest-growing AI-native proptech company, backed by top VCs including YC, Henry serves teams from all major CRE brokerages. With demand outpacing our sales team, we need more AEs, BDRs, and coverage of new segments. Currently, the CEO leads sales alongside running the company, but to scale, we need a full-time leader to coach, strategize, optimize, and drive rapid growth. You’ll get a strong team, a beloved product, and the chance to build a category-defining company, offering a fast track to VP of Sales or CRO. Work directly with a founder who will support your success and empower your leadership.

Responsibilities

• 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. That covers stages, qualification, pricing, and a clean handoff to Account Management for renewals and expansion.

• Pipeline health: Work with marketing and the BDR team to keep the top of the funnel 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. You’ll own the team and the day-to-day, and pull him in at the right moments.

How We Assess

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

• You’ve scaled revenue from mid single digits to mid double digits as the #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

• Player-coach: You’re as comfortable on a live deal as you are running a pipeline review

• 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 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 sold to CRE, capital markets, or financial services; have built a sales team from early stage at a Series A–C startup; or have led both enterprise and high-velocity sales motions

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

Notice to Candidates

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.