TITLE: Vice President of eCommerce Sales - East

REPORTING TO: Chief Revenue Office/CoFounder

LOCATION: New York, NY (onsite M-F)

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 two Vice Presidents of eCommerce—one overseeing the Eastern U.S. and one overseeing the Western U.S.

Each VP will lead revenue growth within their region, build a high-performing team of Account Executives, and expand Flip’s presence among leading eCommerce and retail brands. You’ll be joining a proven, venture-backed AI company with $10M+ in ARR and lead in the key vertical of one of the most important enterprise AI categories.

• This is a role for a hands-on, builder-type sales leader—someone who can both sell and scale
• Own regional revenue for Flip’s eCommerce vertical across DTC, retail, and subscription brands
• Recruit, hire, and develop a world-class AE team; create a culture of excellence and accountability
• Personally lead and close strategic enterprise deals, especially with key strategic accounts
• Establish sales discipline: implement forecasting, pipeline coverage, and territory plans that drive predictability
• Partner cross-functionally with Customer Success, Product, and Marketing
• Represent Flip externally with brand leaders, partners, and at key industry events to position Flip as the category leader in AI for eCommerce

What We’re Looking For

• 2-20 years in SaaS sales leadership, ideally in eCommerce, CX, or retail technology
• Proven experience joining a 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.
• Have an understanding of the eCommerce ecosystem (Shopify, Gladly, Narvar, Gorgias, Attentive, etc.)

Success Metrics

First 90 Days

• • Clear regional GTM plan and hiring roadmap in place
  • First wave of AEs recruited or in final stages; early pipeline built
  • Active participation in closing key strategic deals
  • Forecast and reporting cadence implemented; clear visibility into quarterly performance

6 Months

• • Fully ramped regional team producing consistent pipeline and revenue growth
  • Forecasting accuracy within ±10–15%; strong culture of accountability and execution
  • Documented playbooks for prospecting, qualification, and closing
  • Regional attainment tracking at or above 100% with healthy 3×+ pipeline coverage.

12 Months

• • Region achieving sustained growth of 2×+ year-over-year revenue with predictable attainment
  • Fully staffed, high-performing AE team with strong retention and internal promotion potential
  • Clear operational rigor and forecasting discipline that can scale to additional verticals
  • Recognized internally as a top GTM operator capable of leading broader growth initiatives as Flip scales.

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

#LI-MDAD