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.)