Checkmate

Compensation

Full Description

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: Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows. Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS. 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 ⚡ Think Like a Growth Marketer: Audit brands' conversion funnels, retention strategies, and customer acquisition economics Identify gaps in their cart abandonment flows, email/SMS programs, and anonymous traffic capture Translate Checkmate's capabilities into strategic recommendations tailored to each brand's growth roadmap Speak fluently with CMOs, Growth leads, and Retention marketers about CAC, LTV, cohort analysis, and channel efficiency Understand their tech stack (Klaviyo, Attentive, Yotpo, etc.) and how Checkmate integrates into their existing ecosystem Build Strategic Partnerships Target high-growth Shopify merchants ($10M–$500M GMV) in fashion, beauty, and home verticals Conduct deep discovery to understand growth challenges, constraints, and team priorities Present data-driven business cases showing projected ROAS, incremental revenue, and payback periods Navigate complex buying committees involving Growth, Marketing, RevOps, and Finance stakeholders Establish yourself as a trusted advisor—not just a vendor Drive Revenue Own a quota and manage full-cycle sales from prospecting to close Build pipeline through outbound prospecting, agency partnerships, and ecosystem relationships Maintain disciplined pipeline management and forecasting in Hubspot Support onboarding and identify expansion opportunities based on performance data Shape the Playbook Contribute product feedback based on real customer needs and market gaps Help refine our GTM strategy as we scale into new verticals and use cases Collaborate with Product, Marketing, and Customer Success to improve the customer journey Be a founding member of our sales organization—what you build here will scale Who You Are 🧬 You have growth marketing DNA and want to carry quota 4–7 years in growth, performance, or retention marketing at DTC brands, agencies, or eCommerce platforms Deep understanding of DTC economics: CAC, LTV, ROAS, cohort retention, and conversion optimization Experience with the DTC tech stack (Klaviyo, Attentive, Shopify, etc.) You've built or optimized email/SMS flows, cart abandonment campaigns, or retargeting strategies Understanding of promo strategy, seasonality, and customer segmentation You're commercially driven Comfortable carrying quota and sales accountability Strong discovery skills and ability to build data-driven business cases for senior marketing leaders Entrepreneurial and resourceful—you build your own playbook Passionate about eCommerce and DTC brand strategy You're probably NOT a fit if: You come from pure enterprise SaaS sales with no hands-on marketing experience You can't explain post-purchase flows or LTV:CAC ratios You're looking for a traditional AE role with heavy enablement and structure Bonus Points Agency background (CTC, Noticed, Power Digital, Structured) Management consulting experience focused on eCommerce or growth strategy (Bain, Deloitte Digital) Experience developing GTM strategies in fast-paced SaaS, AI, or eCommerce companies Why Join Checkmate 🚀 Solve real problems: Help DTC brands unlock millions in missed revenue Founding team opportunity: Shape our GTM playbook, working directly with our Head of Ops and Co-Founders Work with top brands: Partner with category leaders like Stanley, Quay, and ColourPop Growth opportunity: Exposure to AI, martech innovation, and fast-moving eCommerce Compensation & Benefits 💸 Equity in a fast-growing, venture-backed company 100% covered healthcare Free gym membership 4 weeks PTO and health days Company retreats 🏝 Remote-first culture (Los Angeles or New York City preferred)