Senior Account Executive — AI-Driven DTC Growth (Remote)

Checkmate; United States; Remote; USD 140,000 - 210,000; Full time

Benefits offered by this job

Equity in a fast-growing company

Comprehensive health coverage

401k plan

4 weeks PTO + health days

Monthly wellness stipend

Company retreats

Job summary

Checkmate is hiring a Sr AE to own full-cycle quota selling into high-growth brands across apparel, beauty, home, and consumer goods. Expect a fast, outbound-driven cadence with deals closing in a few weeks and ROI-driven demonstrations.

You’ll source your own pipeline, run demos, build ROI cases, and close with executives like the VP of Growth or founders. Strong emphasis on DTC and growth marketing know-how.

Qualifications

• 5+ years carrying a quota, including at least 2 years selling directly into brands.
• Experience closing full-cycle deals for a platform, software, adtech, or media product bought by growth/ecommerce leaders.
• Documented, consistent quota attainment with brand logos you personally won.
• Deep fluency in DTC economics (CAC, LTV, ROAS) and the stack brands run on (Shopify, Klaviyo, Attentive, Meta, Google).
• Credibility to sit across from a CMO or VP of Growth and add real value on acquisition, retention, promo strategy, seasonality, segmentation, and incrementality.

Responsibilities

• 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

Skills

Pipeline building

Outbound selling

Demo & ROI

DTC economics

Executive storytelling

Tools

HubSpot

Job description

Checkmate is hiring a Sr AE to own full-cycle quota selling into high-growth brands across apparel, beauty, home, and consumer goods. Expect a fast, outbound-driven cadence with deals closing in a few weeks and ROI-driven demonstrations.

You’ll source your own pipeline, run demos, build ROI cases, and close with executives like the VP of Growth or founders. Strong emphasis on DTC and growth marketing know-how.