Checkmate

Senior Account Executive – DTC, Ecommerce Brands

Checkmate

full-time

Posted on:

Location Type: Remote

Location: United States

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Job Level

Senior

About the role

  • 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
  • **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**
  • 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
Benefits
  • 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.)
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
salesperformance marketingdata-driven business casespipeline managementforecastingDTC economicsemail/SMS flowscart abandonment campaignsretargeting strategiesGTM strategies
Soft Skills
discovery skillsentrepreneurialresourcefulcommercially driventrusted advisorcollaborationpresentation skillsrelationship buildingaccountabilitypassion for eCommerce