Senior Account Executive (DTC and ecommerce brands focus)

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

Requirements

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

Benefits

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.)