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
RequirementsWho 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
BenefitsWhy 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.)
