Remote Chief Mate Jobs (NOW HIRING)

About Checkmate and Mate.
Checkmate is a multichannel offers network loved by 100M shoppers and hundreds of leading brands.
mate. is your AI growth teammate, the eCommerce data network that agentically turns customer intelligence into revenue.
mate finds it, Checkmate goes and gets it. Checkmate is the distribution network, with 100M+ shoppers and 12B+ live intent signals. mate is the AI layer built on top of it: it resolves anonymous visitors, spots the revenue a brand is missing, and builds and executes the campaigns to capture it. Marketers just hit approve.
mate runs six agents for brands:

1. Mate Intelligence: a customer dashboard and AI chatbot that surfaces the revenue a brand is missing.
2. Enrichment: identity resolution that reveals and resolves anonymous visitors.
3. Growth: AI-built, single-use offers delivered across our network and a brand's own channels, priced on performance, with no retainers and no lock-in.
4. Social Activation: enriches social handles into full shopper profiles.
5. LLM Visibility: tracks and grows how a brand shows up in AI search and assistants.
6. Code Leakage: finds leaked discount codes and replaces them with single-use ones.

The combination is rare: a consumer product shoppers love and an AI growth engine brands depend on.
We work with leading brands like Everlane, Brooklinen, and Malbon, and we're backed by Google Ventures, Mantis VS, Fuel Capital, and others.
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 Mate into high-growth ecommerce brands (mainly Shopify brands but we also work with non-Shopify brands as well) across apparel, beauty, home, and consumer goods, typically $15M to $150M+ 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 Mate as a growth channel for brands, 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 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, ecommerce, or adjacent 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 very long sales cycles and 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 brands unlock millions in missed revenue
• Work with top brands: Partner with category leaders like Brooklinen, AG1, and Everlane
• 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
• Competitive medical/dental/vision/other healthcare coverage
• 4 weeks PTO + health days
• 401k plan
• Monthly fitness/wellness stipend
• Company retreats and team get togethers (2x a year)
• Remote-first culture (preference for those near major cities - NYC, LA, SLC, Miami, Chicago, etc.)