Head of Sales

Role Title: Head of Sales

Department: Sales

Location: NYC (in-office Tue-Thu minimum)

Type: Full-time

Reports to: Joe Speiser (CEO)

Compensation: $250K base + uncapped variable (clear path to $450K+)

About Hampton

Hampton is a private network for high-growth founders and CEOs running $3M-$50M businesses. Our members join core groups of 8, where they get the honest conversations, accountability, and connections that come from being in a room with people who actually get it. A $15K annual membership means every person we bring in matters. A bad fit doesn't just churn, they disrupt an entire group.

The Role

This is not a typical high-ticket closer role. We're rebuilding our sales team from the ground up, and we need the architect, not someone who moves into a finished house.

The Head of Sales must be a brand steward who also happens to be a killer operator. Someone who understands that the close is the beginning of a relationship, not the end of a transaction. You will hold member quality as a north star, not a footnote, because every member you bring in joins a core group of 8 real people who are counting on Hampton to get it right.

What You've Done (Non-Negotiables)

Sold high-ticket ($10K+/yr) directly to founders or CEOs, and genuinely enjoyed that conversation.
Built a sales team from scratch. Defined the playbook, set the culture, hired the reps, established the cadence. Not inherited a system and optimized it. Built it.
Personally carried a bag. This is a player-coach role. You will be on sales calls, not watching from the sidelines. If the last time you personally closed a deal was 3+ years ago, you're probably not it.
Managed, coached, and held reps accountable. Call reviews, structured 1:1s, rep development, and yes, letting people go when needed.
Thought beyond your own team's numbers. You've worked cross-functionally with member success, community, or ops to make sure the people you brought in actually belonged and stuck around.

Who You Are

Confident. You walk into a room and own it, but you inspire people, you don't intimidate them.
Energizing. You give the team energy, not drain it. People feel better after talking to you.
Data-driven. You read a pipeline the way a surgeon reads a chart. You know your numbers cold, including retention and refund rates, not just close rate.
AI-forward. You use AI for leverage and logic, not as a crutch. You ignore it when human judgment is called for.
Radically candid. You give and receive hard feedback without making it personal.
Competitive. Obsessed with hitting the number, but never by cutting corners or jamming in bad fits.
Brand-aware. You would push back on a rep closing someone who shouldn't be a member. You get that a bad member costs more than a missed sale.
Team-first. You build an environment where reps root for each other. No "every rep for themselves" dynamics.
A steward. You see member fit as your responsibility. You understand that a wrong-fit member disrupts a whole core group.

Green Flags

You've sold to founder/CEO buyers and can speak fluently about what that dynamic is like.
Your track record includes both building the process AND being in the weeds executing it.
You ask about refund rates and member retention, not just top-of-funnel metrics.
You have a story about a deal you turned down because the prospect wasn't the right fit.
You talk about your team's wins as "we," not just your own quota attainment.
You've collaborated closely with customer success, community, or ops to close the loop on member quality.
You've sold in environments where culture fit was part of the close, not just price and features.
You actively use AI to improve pipeline hygiene, call prep, or follow-up, with specific examples.
You're comfortable in a scrappy, high-growth environment.

Compensation & Perks

$250K base + uncapped variable (clear path to $450K+)
Health, Vision, and Dental Insurance
Unlimited time off
401(k) with company match

By submitting your application, you agree that Hampton may collect your personal data for recruiting and related purposes.