Founding Sales Lead

Stealth Vertical AI Startup; New York (NY); On-site; USD 150,000 - 260,000; Full time

Benefits offered by this job

Equity

High earning potential

Medical, dental, vision insurance

Lunch & fitness stipend

Office in Williamsburg

In-person, five days a week

Job summary

Autumn, a Brooklyn-based AI startup building an operating system for independent hotels, is seeking a Founding Sales Lead to shape its commercial organization from the ground up. You will personally close hotels each week and design the playbook, processes, metrics, tooling, and team that scale the motion.

You will hire, onboard, and coach the sales team, own the number, and report directly to the founders.

Qualifications

• 3–10 years in sales with high-velocity, short-cycle closes.
• Evidence of building or reshaping a sales motion at a startup.
• Experience coaching or leading reps and improving performance.
• Systems thinking: segmentation, metrics, and process design.
• Ability to automate repetitive work with AI and data-driven insights.

Responsibilities

• Close hotels personally every week in a high-velocity motion.
• Write the sales playbook: messaging, qualification, objections, follow-up.
• Run pipeline hygiene, forecasting, and weekly cadence.
• Set strategy on market segments, positioning, and demand pockets.
• Sharpen top-of-funnel with outbound messaging and feedback loops.
• Build and coach the sales team, set targets, and own outcomes.
• Provide market feedback to product and leadership on objections and pricing.
• Leverage AI to automate prep, follow-up, and admin tasks.

Skills

Sales experience

Quota attainment

System thinking

Leadership

Analytical

AI-driven selling

Job description

About Autumn

Autumn is building the AI operating system for independent hotels.

Hotels are still run on an extraordinarily fragmented stack of legacy software, agencies, spreadsheets, and manual workflows. We are building one AI native platform to automate that work, starting with the workflows closest to revenue, specifically digital marketing.

The early sales motion is already working. Most of our growth to date has come from cold outbound, and we convert 85% of calls into customers with a one-call close because we're solving a true hair-on-fire problem.

We recently raised the largest seed round in hotel tech history, led by Bessemer, and are building an exceptional team in person from our waterfront office in Williamsburg.

We are now looking for a Founding Sales Lead to build Autumn's commercial organization from the ground up.

The Role

This is a player-coach role for someone who has been an exceptional closer and is ready to build the system other people sell inside.

You will close hotels yourself every week, and you will use what you learn to define how Autumn sells: the playbook, the process, the metrics, the tooling, and the team. In the first months most of your time is in the motion, running discovery, demos, and closes with independent hotel owners and operators. Alongside that you will write the playbook, stand up pipeline reviews and forecasting, decide what a qualified hotel looks like, and set how we segment and prioritize the market.

As the system proves out, you will hire into it. You will scope, recruit, onboard, and coach the sales team, and own its number.

You will work directly with the founder and be the voice of the market inside the company: which segments are pulling, what is blocking deals, and what the product should do next.

What You'll Do

• Close. Carry a personal number and run the full cycle from first conversation through close, at the volume this motion demands.
• Write the playbook. Turn hundreds of conversations into a repeatable system: messaging by segment, qualification criteria, objection handling, follow up cadence, and handoff to Customer Success.
• Run the pipeline. Own pipeline hygiene, forecasting, and the weekly operating rhythm. Know exactly where the number is coming from and why.
• Set the strategy. Decide which hotel segments to prioritize, how to position and package the product for each, and where the next pockets of demand are.
• Sharpen the top of funnel. Partner with the GTM team on outbound messaging, lead quality feedback loops, and sequence performance. Define what good looks like.
• Build the team. Scope, recruit, onboard, and coach sales hires. Set targets and hold the team to them.
• Bring the market back to the founders. Deliver structured insight to product and leadership: recurring objections, segment differences, pricing signals, competitive moves.
• Use AI as leverage. Build an AI native sales operation where research, preparation, follow up, and administrative work are automated so people spend their time selling.

What We're Looking For

Above all, we are looking for someone who has proven they can sell at high velocity and has already started building the system around it.

You are likely a strong fit if:

• You have 3 to 10 years in sales, including several years consistently beating quota in a short sales cycle, high volume motion (SMB or mid market SMB)
• You have built or materially rebuilt a sales motion before: first sales hire at a startup, team lead, player-coach, or the person who wrote the playbook everyone else used
• You have managed or coached reps, formally or informally, and people got better because of you
• You think in systems: segments, conversion rates, cycle length, capacity, and what to change to move each one
• You build trust quickly and sell with warmth and credibility rather than pressure
• You are analytical, unusually organized, and accountable for outcomes
• You naturally look for ways to automate repetitive work with AI, and expect your team to as well
• You want to own a number and a function, not one or the other
• You want to work around ambitious people in person and move very quickly

Preferred (Not Required)

• Have sold hotel or hospitality technology
• Have sold vertical SaaS to owner operated businesses
• Understand performance marketing, paid search, SEO, websites, or other revenue generating products
• Have experience in an early stage startup
• Have worked with independent hotels or short term rental operators
• Speak Spanish fluently

None of these are required if you are an exceptional seller who has built before.

Why This Role Is Unusual

You are joining after the product has demonstrated real commercial pull, but before the sales organization has been built.

That means you get both: something that already sells, and the mandate to decide how it gets sold.

You will have:

• A product solving a clear and measurable customer problem
• A short sales cycle and high volume of opportunities
• Meaningful top of funnel support
• Direct access to the founders
• Ownership of how Autumn sells, from playbook to team
• An AI native sales environment designed to remove administrative work
• Uncapped earning potential
• Meaningful equity
• The opportunity to build Autumn's commercial organization from its foundation
• Highly competitive cash & equity comp
• Top tier medical, dental, and vision coverage
• Lunch and fitness stipend
• Beautiful private waterfront office in Williamsburg
• Five days a week in person with a small, highly ambitious team

Location

This role is five days a week in person in Brooklyn, New York.