Account Executive, DTC and Ecommerce Brands Focus

🕒 April 22

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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

• **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** 🧬**You understand the e-commerce landscape and have experience selling into brands** • - 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.)