Remote, United States

The Problem We’re Solving 🎯

Most DTC brands are leaving revenue on the table. They spend millions acquiring customers through paid channels, then lose 60%+ of high-intent shoppers to cart abandonment, anonymous browsing, and missed retargeting opportunities.

The issue isn't traffic—it's conversion architecture. Brands lack the infrastructure to capture intent signals, recognize returning visitors, and re-engage shoppers at the moments that matter most.

That's where Checkmate comes in. Our AI-powered platform captures shopping intent from 100M+ shoppers across the web—wishlists, carts, browsing sessions—and turns it into high-converting campaigns that consistently deliver revenue uplift in 30 days.

But here's the thing: selling this solution requires more than a good pitch deck. It requires someone who can walk into a growth team's meeting, diagnose where they're leaving money on the table, and prescribe a strategic path forward.

About Checkmate 🛍 📲

Checkmate is an AI marketing platform that helps DTC brands capture anonymous shoppers, launch targeted campaigns, and drive measurable revenue.

Our platform uses AI to de-anonymize site traffic, uncover missed conversion opportunities, and launch high-performance campaigns that engage the 100M+ high-intent shoppers in our network. We offer three core products for brands:

  1. Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows.
  2. Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS.
  3. Audiences: Capture pre-checkout emails via gated discounts and gain competitive insights.

We work with leading DTC brands like Stanley, Quay, ColourPop, Laneige, and Dockers. Backed by Google Ventures, Fuel Capital, and others.

The Role 💼

This isn't a traditional AE role. You'll function as a strategic growth advisor who happens to carry quota. Focusing on the fashion, beauty, and home verticals, you'll diagnose conversion problems, prescribe solutions, build trusted partnerships with DTC growth teams, and then close and expand those relationships.

You'll be a founding member of our sales team, working directly with our Head of Ops and Co-Founders to build the GTM playbook as we scale.

What You’ll Do