About Checkmate 🛍 📲
Checkmate is a multichannel offers network loved by 100M shoppers and 450+ leading brands.
For shoppers, it's how they discover and save on the brands they love, with personalized cashback and offers across our app, email, and SMS.
For brands, it's a new channel to reach and convert high-intent shoppers they can't find anywhere else. Hundreds of leading brands, including Brooklinen, Quay, and Summer Fridays, use Checkmate to drive incremental revenue, paying only when we deliver a sale.
The combination is rare: a consumer product shoppers love and a performance engine brands depend on, powered by AI that knows exactly who to reach and how to convert.
Backed by GV, Mantis VC, and DST Global. We're a remote-first team with hubs in LA and NYC, and a preference for hiring in or near major cities.
The Role 💼
As a Sr AE, you'll own a full-cycle quota selling Checkmate into high-growth ecommerce brands (mainly on Shopify) across apparel, beauty, home, and consumer goods, typically $10M to $100M+ in GMV. This is a high-velocity sale: most deals close in two to three calls over a few weeks. You'll source your own pipeline, run the demo, build an ROI case, and close. Our pitch is focused on positioning Checkmate as a channel for increasing revenue, not selling a long enterprise contract.
If you've sold a performance, martech, or media product into ecommerce brands and like the pace of a short, outbound-driven cycle, this will feel like home.
What You’ll Do ⚡
- 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
Who You Are 🧬
- You thrive in a fast, high-volume cycle and can run the whole thing yourself, prospect to close
- You build your own pipeline and earn deals, rather than waiting on inbound to come your way
- You sell like a partner, diagnosing the real problem and earning trust instead of pushing product
- You're genuinely curious about ecommerce and what makes brands grow
- You're entrepreneurial and resourceful—you build your own playbook
What You Bring 🎒
- 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
Bonus Points
- You've operated inside a DTC brand at a senior growth or ecommerce level
- You've been an early or founding AE who helped build the motion
- You bring relationships across the ecommerce ecosystem
You're probably NOT a fit if:
- You come from pure enterprise SaaS sales with no experience in the ecommerce industry
- You're looking for a traditional AE role with heavy enablement and structure
Why Join Checkmate 🚀
- 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
Compensation & Benefits 💸
- 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.)