Sales Account Executive
Checkmate Savings, Inc
Sales & Business Development
United States · Remote
Posted on Dec 2, 2025
Remote, United States
The Problem We’re Solving
Most DTC brands are leaving revenue on the table. They spend millions acquiring customers through paid channels, then lose 60%+ of high-intent shoppers to cart abandonment, anonymous browsing, and missed retargeting opportunities.
The issue isn't traffic—it's conversion architecture. Brands lack the infrastructure to capture intent signals, recognize returning visitors, and re-engage shoppers at the moments that matter most.
That's where Checkmate comes in. Our AI-powered platform captures shopping intent from 100M+ shoppers across the web—wishlists, carts, browsing sessions—and turns it into high-converting campaigns that consistently deliver revenue uplift in 30 days.
But here's the thing: selling this solution requires more than a good pitch deck. It requires someone who can walk into a growth team's meeting, diagnose where they're leaving money on the table, and prescribe a strategic path forward.
About Checkmate
Checkmate is an AI marketing platform that helps DTC brands capture anonymous shoppers, launch targeted campaigns, and drive measurable revenue.
Our platform uses AI to de-anonymize site traffic, uncover missed conversion opportunities, and launch high-performance campaigns that engage the 100M+ high-intent shoppers in our network. We offer three core products for brands:
Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows.
Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS.
Audiences: Capture pre-checkout emails via gated discounts and gain competitive insights.
We work with leading DTC brands like Stanley, Quay, ColourPop, Laneige, and Dockers. Backed by Google Ventures, Fuel Capital, and others.
The Role
This isn't a traditional AE role. You'll function as a strategic growth advisor who happens to carry quota. Focusing on the fashion, beauty, and home verticals, you'll diagnose conversion problems, prescribe solutions, build trusted partnerships with DTC growth teams, and then close and expand those relationships.
You'll be a founding member of our sales team, working directly with our Head of Ops and Co-Founders to build the GTM playbook as we scale.
What You’ll Do
Think Like a Growth Marketer:
Audit brands' conversion funnels, retention strategies, and customer acquisition economics
Identify gaps in their cart abandonment flows, email/SMS programs, and anonymous traffic capture
Translate Checkmate's capabilities into strategic recommendations tailored to each brand's growth roadmap
Speak fluently with CMOs, Growth leads, and Retention marketers about CAC, LTV, cohort analysis, and channel efficiency
Understand their tech stack (Klaviyo, Attentive, Yotpo, etc.) and how Checkmate integrates into their existing ecosystem
Build Strategic Partnerships
Target high-growth Shopify merchants ($10M–$500M GMV) in fashion, beauty, and home verticals
Conduct deep discovery to understand growth challenges, constraints, and team priorities
Present data-driven business cases showing projected ROAS, incremental revenue, and payback periods
Navigate complex buying committees involving Growth, Marketing, RevOps, and Finance stakeholders
Establish yourself as a trusted advisor—not just a vendor
Drive Revenue
Own a quota and manage full-cycle sales from prospecting to close
Build pipeline through outbound prospecting, agency partnerships, and ecosystem relationships
Maintain disciplined pipeline management and forecasting in Hubspot
Support onboarding and identify expansion opportunities based on performance data
Shape the Playbook
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
Collaborate with Product, Marketing, and Customer Success to improve the customer journey
Be a founding member of our sales organization—what you build here will scale
Who You Are
You have growth marketing DNA and want to carry quota
4–7 years in growth, performance, or retention marketing at DTC brands, agencies, or eCommerce platforms
Deep understanding of DTC economics: CAC, LTV, ROAS, cohort retention, and conversion optimization
Experience with the DTC tech stack (Klaviyo, Attentive, Shopify, etc.)
You've built or optimized email/SMS flows, cart abandonment campaigns, or retargeting strategies
Understanding of promo strategy, seasonality, and customer segmentation
You're commercially driven
Comfortable carrying quota and sales accountability
Strong discovery skills and ability to build data-driven business cases for senior marketing leaders
Entrepreneurial and resourceful—you build your own playbook
Passionate about eCommerce and DTC brand strategy
You're probably NOT a fit if:
You come from pure enterprise SaaS sales with no hands-on marketing experience
You can't explain post-purchase flows or LTV:CAC ratios
You're looking for a traditional AE role with heavy enablement and structure
Bonus Points
Agency background (CTC, Noticed, Power Digital, Structured)
Management consulting experience focused on eCommerce or growth strategy (Bain, Deloitte Digital)
Experience developing GTM strategies in fast-paced SaaS, AI, or eCommerce companies
Why Join Checkmate
Solve real problems: Help DTC brands unlock millions in missed revenue
Founding team opportunity: Shape our GTM playbook, working directly with our Head of Ops and Co-Founders
Work with top brands: Partner with category leaders like Stanley, Quay, and ColourPop
Growth opportunity: Exposure to AI, martech innovation, and fast-moving eCommerce
Compensation & Benefits
Equity in a fast-growing, venture-backed company
100% covered healthcare
Free gym membership
4 weeks PTO and health days
Company retreats
Remote-first culture (Los Angeles or New York City preferred)
How to Apply
If you're a growth marketer ready to jump into sales - or a strategic thinker who speaks the language of DTC growth - we want to hear from you.
Submit your resume and a note on why you're excited about Checkmate and eCommerce to careers@c.inc
