CareersFounding Account Executive

Founding Account Executive

GTM
New York City
Full time
AI Native Operating System for Hotels

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 Account Executive who wants to become a foundational part of Autumn's commercial organization.

The Role

This is a high velocity closing role for someone who loves winning.

You will own new business from first conversation through close, primarily selling to independent hotel owners and operators. Sales cycles are short, deal volume is high, and you will have many opportunities moving simultaneously.

You will not be building pipeline alone. We are investing heavily in outbound infrastructure and top of funnel support so that a great AE can spend the majority of their time doing what they do best: talking to customers and closing.

At the same time, this is an early stage company. You will work directly with the founder and have a real voice in how Autumn sells, including messaging, qualification, objection handling, tooling, and the operating cadence behind the sales engine.

For the right person, this role can grow well beyond an individual contributor seat. We expect to build a meaningful sales organization as Autumn scales, and someone who proves they can consistently outperform, improve the motion, and raise the bar for others could grow into a sales leadership role and help build the team around them.

What You'll Do

  • Close at volume. Run discovery, demos, objection handling, follow up, negotiation, and closing across a high number of opportunities.
  • Own your number. Maintain exceptional pipeline discipline and know exactly what needs to happen to hit and outperform target.
  • Qualify aggressively. Autumn succeeds when our customers succeed. Knowing which hotels are likely to perform well matters just as much as knowing how to close them.
  • Use AI as leverage. Automate research, preparation, follow up, personalization, and administrative work so more of your time goes toward selling.
  • Become exceptional at the hotelier buyer. Understand how independent hotel owners think, what they care about, and how to earn credibility quickly.
  • Make the motion better. Identify patterns across hundreds of conversations and continuously improve messaging, qualification, objection handling, and process.
  • Sharpen the top of funnel. Work closely with the team on outbound messaging, lead quality feedback loops, and sequence performance.
  • Bring the market back to the founders. Surface recurring objections, customer needs, segment differences, and insights that should influence product and go to market decisions.
  • Hand off customers cleanly. Make sure Customer Success has the context needed to get every new property live quickly and successfully.

What We're Looking For

Above all, we are looking for someone who has proven they can sell at high velocity. You are likely a strong fit if:

  • You have 3 to 7 years of closing experience in SMB, mid market SMB, or another high volume environment
  • You have consistently beaten quota in a short sales cycle motion
  • You are comfortable managing dozens of active opportunities without letting follow up slip
  • You build trust quickly and sell with warmth and credibility rather than pressure
  • You are excellent at discovery and know when to push, when to listen, and when to walk away
  • You are competitive and deeply motivated by performance
  • You are unusually organized, reliable, and accountable for outcomes
  • You naturally look for ways to automate repetitive work with AI
  • You are analytical and notice what is working across many conversations, then adjust quickly
  • You are comfortable operating with significant autonomy and limited process
  • You want meaningful ownership rather than a perfectly defined corporate sales environment
  • You want to work around ambitious people in person and move very quickly

If your recent experience has primarily been six figure enterprise contracts with six month sales cycles, this is probably a different sport.

Preferred (Not Required)

  • Understand performance marketing, paid search, SEO, websites, or other revenue generating products
  • Have sold hotel or hospitality technology
  • Have sold vertical SaaS to owner operated businesses
  • Have sold into restaurants, fitness, home services, local businesses, or other SMB categories
  • 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 high velocity seller.

What Winning Looks Like

  • In your first 30 days, you understand the product, buyer, positioning, and sales process well enough to run conversations independently.
  • Within 60 days, you are operating a full pipeline, closing customers consistently, and developing strong instincts around which properties are most likely to succeed with Autumn.
  • Once fully ramped, you are closing 15+ new customers every week, consistently outperforming your number, and contributing ideas that make the entire sales motion better.

Over time, the strongest person in this seat should become much more than someone who closes deals. We want someone who can help define how Autumn sells, raise the standard for future hires, and potentially grow into a sales leadership role as the team expands.

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 opportunity to shape 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
  • Significant autonomy over how you operate
  • An AI native sales environment designed to remove administrative work
  • Uncapped earning potential
  • Meaningful equity
  • The opportunity to influence the foundation of Autumn's commercial organization

And for someone who wants to lead eventually, there is a genuine path.

We are hiring our first exceptional AE before building out a larger sales organization. If you become the person who understands the motion best, consistently delivers, and can make others better, you will be in a natural position to take on increasing leadership responsibility as the team grows.

We want someone who is excited to earn the right to lead. Someone who wants to be an exceptional individual contributor today, but could ultimately build, coach, and lead a high performing sales team.

Compensation & Benefits

  • $130K to $250K+ uncapped OTE
  • Equity
  • 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.