Senior Account Executive – DTC, Ecommerce Brands

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Checkmate

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2022

🛍️ eCommerce

🤖 Artificial Intelligence

👥 B2C

💰 $15M Series A on 2023-06

eCommerce • Artificial Intelligence • B2C

Checkmate is an AI-powered shopping network and browser extension/app that personalizes offers and coupon codes based on who you are and your shopping behavior. It aggregates merchant deals and exclusives, surfaces curated collections and trending savings, and provides an app and Chrome extension to help consumers discover and unlock targeted discounts while shopping online.

📋 Description

• Build your own pipeline through outbound, agency partners, events, and your own network • Run discovery and demos, and build ROI cases around the incremental revenue Checkmate can drive • Move deals to close in a handful of calls, usually with a VP of Growth, ecommerce lead, or founder • Carry and hit a GMV-based quota, closing at volume • Sell the full product line (Targeting, Cashback) and adapt and help shape the pitch as we launch new products • Support onboarding and identify expansion opportunities based on performance data • Keep pipeline and forecasts clean in HubSpot • 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

🎯 Requirements

• 5+ years carrying a quota, including at least 2 years selling into DTC or ecommerce brands • Experience closing full-cycle deals for a platform, software, performance, adtech, or media product bought by growth, marketing, or ecommerce leaders, and a clear view of why that maps to Checkmate • Documented, consistent quota attainment, with specific brand logos you personally won • Deep fluency in DTC economics (CAC, LTV, ROAS) and the stack brands run on (Shopify, Klaviyo, Attentive, Meta, Google, attribution and retention tooling) • The credibility to sit across from a CMO or VP of Growth and add real value on acquisition, retention, promo strategy, seasonality, segmentation, and incrementality

🏖️ Benefits

• Solve real problems: Help DTC brands unlock millions in missed revenue • Work with top brands: Partner with category leaders like Brooklinen, Quay, and ColourPop • Growth opportunity: Exposure to AI, martech innovation, and fast-moving eCommerce • Competitive base salary + commission package • Equity in a fast-growing, venture-backed company • Traditional medical/dental/vision/other healthcare coverage • 4 weeks PTO + health days • 401k plan • Monthly gym membership reimbursement • Company retreats and team get togethers 🏝 • Remote-first culture (preference for those near major cities - NYC, LA, SLC, Miami, Chicago, etc.)