TITLE: Vice Presidents of Sales

REPORTING TO: CoFounder

LOCATION: LA or NYC (Onsite Monday - Friday)

Who The Flip Is Flip?

Ever call your favorite eCommerce brand, and have a crazy good Voice AI answer? That’s Flip. Hundreds of brands from Brooklinen, Princess Polly, and Hexclad Cookware, to Tory Burch, Belk and the NFL trust Flip to have millions of phone calls with their customers every year.

We’ve built our company on the idea that the best way to grow is to have a reference list as long as our customer list, and a constant belief that the team is the best thing we’ve built. Both are true today and increasingly so every day.

Many on our team would tell you this is their favorite place they’ve ever worked, and the hardest they’ve ever worked. It’s ideal for people who want to go all-in, do the work, ride the roller coaster, and have a great Flippin time doing it. We’re a small and mighty team of 50 today with offices in NYC, LA, and the UK.

What You’ll Do

We’re expanding our leadership team with a Vice President of Sales to lead revenue growth and scale Flip’s go-to-market motion.

You’ll join a proven, venture-backed company with $15M+ in ARR, operating in one of the most important and fastest-growing enterprise AI categories. This is a hands-on, builder-type leadership role for someone who can both sell and scale.

• Own and grow revenue across Flip’s sales organization
• Recruit, hire, and develop a world-class AE team; build a culture of excellence, accountability, and execution
• Personally lead and close strategic enterprise deals, particularly high-impact, marquee accounts
• Establish sales rigor and discipline, including forecasting, pipeline coverage, and operating cadence to drive predictability
• Partner closely with Customer Success, Product, and Marketing to align execution across the full customer lifecycle
• Represent Flip externally with customers, partners, and at industry events, positioning Flip as a category-defining AI company

What We’re Looking For

• Proven experience joining a SaaS company between $5M–$25M ARR and helping scale to $100M+ ARR
• Demonstrated success hiring, coaching, and retaining top-performing AEs. Competitive, relentless winners
• Hands-on operator—comfortable running deals, building process, and scaling simultaneously
• High EQ and low ego—thrives in a founder-led, fast-moving environment
• Builder mentality—not just managing what exists, but creating what’s next

Bonus points:

• You bring one or two top-performing AEs or Sales Managers who trust you and want to build with you

More About Us

• We're international, spanning the US, UK, and Canada
• We’ve raised +$30M to date including our recent $20M Series A - backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon Data
• Comprehensive healthcare and unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year
• In office 5 days/week

#FlippinLegend