Role Overview
What You’ll Do ⚡
- Think Like a Growth Marketer:
- Audit brands' conversion funnels, retention strategies, and customer acquisition economics
- Identify gaps in their cart abandonment flows, email/SMS programs, and anonymous traffic capture
- Translate Checkmate's capabilities into strategic recommendations tailored to each brand's growth roadmap
- Speak fluently with CMOs, Growth leads, and Retention marketers about CAC, LTV, cohort analysis, and channel efficiency
- Understand their tech stack (Klaviyo, Attentive, Yotpo, etc.) and how Checkmate integrates into their existing ecosystem
- 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 have growth marketing DNA and want to carry quota
- 4–7 years in growth, performance, or retention marketing at DTC brands, agencies, or eCommerce platforms
- Deep understanding of DTC economics: CAC, LTV, ROAS, cohort retention, and conversion optimization
- Experience with the DTC tech stack (Klaviyo, Attentive, Shopify, etc.)
- You've built or optimized email/SMS flows, cart abandonment campaigns, or retargeting strategies
- 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
- 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
- Founding team opportunity: Shape our GTM playbook, working directly with our Head of Ops and Co-Founders
- 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 💸
- Equity in a fast-growing, venture-backed company
- 100% covered healthcare
- Free gym membership
- 4 weeks PTO and health days
- Company retreats 🏝
- Remote-first culture (Los Angeles or New York City preferred)