Account Executive (DTC and ecommerce brands focus)

Overview 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. Checkmate is an AI-powered platform that 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. Checkmate helps growth teams diagnose where money is being left 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. Products 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 and are backed by notable investors. The Role This isn't a traditional AE role. You'll function as a strategic growth advisor who also carries quota. Focusing on the fashion, beauty, and home verticals, you'll identify brands in our ICP, diagnose their conversion problems, prescribe compelling solutions with Checkmate's product offerings, build trusted partnerships with DTC growth teams, and then close those relationships. What You’ll Do 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 Requirements Who You Are 2-5+ years in sales, growth, performance marketing, or equivalent at DTC brands, agencies, or eCommerce platform You have at least 2 years of direct experience selling into DTC or ecomm brands Deep understanding of DTC economics (CAC, LTV, ROAS) and the DTC tech stack (Klaviyo, Attentive, Shopify, etc.) You understand email/SMS flows, cart abandonment campaigns, or retargeting strategies enough to speak to prospects about them 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 marketing experience 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 Benefits Why Join Checkmate Solve real problems: Help DTC brands unlock millions in missed revenue 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 Competitive base salary + commission package Equity in a fast-growing, venture-backed company Traditional medical/dental/vision/other healthcare coverage 401k plan Free gym membership Company retreats Remote-first culture (preference for those near major cities - NYC, LA, Miami, Chicago, etc.) #J-18808-Ljbffr