Windmill is building an autonomous management system — AI that handles the work of managing people so that managers can focus on actually leading them. We're starting with performance reviews, but that's just the beginning. The vision is a platform that runs the entire management operating system: goals, feedback, development, coaching, and more. We have over 100 customers and growing fast. The incumbents are outdated, and we've already built something that HR leaders and employees genuinely love.

We're ready to build a sales team. Our Co-Founder and President has been the company's main salesperson since day one, and now it's time to scale. We need salespeople who will relentlessly bring autonomous management to every corner of the globe. As a founding Account Executive, you'll be on the ground floor of a company that we believe will be the most important built in NYC this decade.

This role is in-person, 5 days a week, in our NYC office.

Compensation: $200K OTE ($100K base + $100K commission) + generous equity package

We are looking for candidates who are:

• Competitive by nature — you hate losing more than you love winning. You were the kid who turned every game into a blood sport. You're always training for something.

• Winners — you have a track record of achievement, and it doesn't have to be in sales or tech. You were the captain of your team. Set some sort of individual record. You found a way to challenge yourself and overcome obstacles at every stage of your life.

• Coachable — your manager gives you feedback on Monday morning. By Monday afternoon, you've already changed your approach and have improved.

• Curious — on a demo, you're the one asking the question the prospect didn't even know they needed to answer. You dig until you understand the real problem, not just the surface one.

• Quick on their feet — when a prospect throws you a curveball, you don't freeze. You reframe the conversation and turn it into a selling moment without missing a beat.

• Resilient — you get told "no" nine times and your energy on the tenth call is the same as the first. Rejection doesn't slow you down — it fuels you.

• AI curious — you are constantly learning about the latest AI tools to make yourself better.

• Hard workers — you're the first one in and the last to leave. Not because someone's watching, but because that's just who you are.

• People of integrity — you'd rather lose a deal than win it the wrong way. You tell prospects the truth even when it costs you money.

• Humble — you closed the biggest deal of the quarter and the first thing you did was thank the engineers and product team. You're confident, not arrogant.

• Optimistic — a prospect ghosts you after three great calls and you genuinely believe the fourth follow-up is the one that lands. You see the opportunity in every setback.

The right candidates have:

• 2–5 years of direct sales experience as an Account Executive

• Experience selling into tech companies

• Track record closing deals that require contracts and are >$25K

• Based in or willing to relocate to New York City

But the resume is the least interesting part. What we really care about is who you are.

You have two choices: apply and hope it stands out, or apply and find a way to get in front of us directly. We respect hustle.

Windmill is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.