Enterprise Account Executive
Checkmate
Remote · USJobPosted 1 day agoStill listed today
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At a glance
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Job overview
Checkmate is hiring an Enterprise Account Executive to sell its performance channel to large brands across ecommerce and other sectors. The role owns a full-cycle quota, builds pipeline, runs discovery and demos, develops business cases, and closes strategic deals. The AE will also grow partnerships, maintain forecasts in HubSpot, share customer feedback, and help shape the enterprise go-to-market strategy.
Skills & qualifications
Skills
Qualifications
Benefits
Full job description
About mate. and Checkmate 🛍 📲 mate. is a shopping platform that millions of shoppers trust for rewards, and a performance channel that helps brands reach and convert their next million customers. mate uses live intent signals across 100M+ shoppers to find who's in market. It then reaches them with personalized offers by email, in our app, through our AI shopping agent, and on top publisher partners. More than 1,000 companies trust mate, including Everlane, Brooklinen, Liquid I.V., and Laneige. We're backed by Google Ventures, Fuel Capital, and others. We know ecommerce cold, and now we're bringing the same network to bigger brands, both in and outside of ecommerce. 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 an Enterprise AE, you'll own a full-cycle quota selling mate into large brands across ecommerce and beyond. These are bigger, more strategic deals than our core sale, with more stakeholders and a longer path to close. You'll build your own pipeline, run discovery and demos, build a business case, and close. Our pitch positions mate as a performance channel that drives incremental revenue. If you've sold a performance, adtech, or media product into large brands and know how to land and expand an enterprise account, 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 business cases around the incremental revenue mate can drive
- Sell to growth and marketing leaders, and build relationships across their teams
- Land new partnerships and grow them into larger, long-term budgets
- Carry and hit a revenue-based quota
- Sell the full product line, and help shape the enterprise pitch as we launch new products
- Keep pipeline and forecasts clean in HubSpot
- Share product feedback based on real customer needs and market gaps
- Help build our enterprise GTM strategy as we scale into new verticals
Requirements
Who You Are 🧬
- You can run a complex deal yourself, from first touch to signed contract
- You build your own pipeline and earn deals, rather than waiting on inbound
- You sell like a partner, diagnosing the real problem and earning trust instead of pushing product
- You're curious about AI, adtech, 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 closing enterprise deals
- Experience closing full-cycle deals for a performance, adtech, or media product bought by growth or marketing leaders at large brands
- Documented, consistent quota attainment, with specific logos you personally won
- Deep fluency in performance marketing (CAC, LTV, ROAS, incrementality) and how large brands buy media
- The credibility to sit across from a CMO or VP of Growth and add real value on acquisition, retention, and measurement
Bonus Points
- You've sold for an ad network, social ad platform, or CTV platform
- You've been an early enterprise AE who helped build the motion
- You bring relationships with growth leaders at large brands
You're probably NOT a fit if:
- You've only sold high-velocity SMB or mid-market deals
- You're looking for a traditional AE role with heavy enablement and structure
Benefits
Why Join Checkmate 🚀
- Solve real problems: Help large brands find revenue their other channels are missing
- Work with top brands: Partner with category leaders like Brooklinen, Liquid I.V., and Everlane
- Growth opportunity: Exposure to AI and adtech innovation, and the chance to help build our enterprise motion
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, Miami, Chicago, SLC, Austin, etc.)
How this job compares
Set against the 4,924 open Enterprise Sales jobs on Olive Jobs, counted November 14, 2026.
- Pay
- This postingNot listed
- US median$140–209K/yr3,959 salary ranges
- Openings
- Olive Jobs lists 4,924 open Enterprise Sales jobs across the US. 22% of them nationwide are listed as remote or flexible.
- Experience
- This posting asks for at least 5 years of experience; Enterprise Sales postings that state a minimum ask for 7 years at the median (4,229 postings).
- Education
- 371 of the 4,924 open Enterprise Sales jobs (8%) ask for a bachelor's degree or higher.
Counted across the open, public US postings on Olive Jobs on November 14, 2026. Figures based on too few postings are left out.
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