Account Executive (Sales), DTC Brands

Checkmate is an AI marketing platform that assists DTC brands in capturing anonymous shoppers and driving measurable revenue. The role of Account Executive involves functioning as a strategic growth advisor, building partnerships with brands in the fashion, beauty, and home verticals, diagnosing their conversion challenges, and prescribing solutions using Checkmate's offerings.

Responsibilities:

• 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:

• 4-7 years in sales, growth, performance marketing, or equivalent at DTC brands, agencies, or eCommerce platforms
• 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
• 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
• Direct experience selling into DTC or ecomm brands
• 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