Senior Account Executive (DTC and ecommerce brands focus)

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:

1. Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows.
2. Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS.
3. 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 also carries quota. Focusing on the fashion, beauty, and home verticals, you'll identify brands in our ICP, diagnose their conversion problems, prescribe compelling solutions with Checkmate's product offerings, build trusted partnerships with DTC growth teams, and then close those relationships.

What You’ll Do ⚡

• 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 understand the e-commerce landscape and have experience selling into brands

• 4–7 years in sales, growth, performance marketing, or equivalent at DTC brands, agencies, or eCommerce platforms
• Deep understanding of DTC economics (CAC, LTV, ROAS) and the DTC tech stack (Klaviyo, Attentive, Shopify, etc.)
• You understand email/SMS flows, cart abandonment campaigns, or retargeting strategies enough to speak to prospects about them
• 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

• Direct experience selling into DTC or ecomm brands
• 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
• 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 💸

• Competitive base salary + commission package
• Equity in a fast-growing, venture-backed company
• Traditional medical/dental/vision/other healthcare coverage
• 401k plan
• Free gym membership
• Company retreats 🏝
• Remote-first culture (preference for those near major cities - NYC, LA, Miami, Chicago, etc.)