Head of Marketing

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.

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:

We work with leading DTC brands like Stanley, Quay, Colour Pop, Laneige, and Dockers. Backed by Google Ventures, Fuel Capital, and others.

-------------------------------------------------------------

Checkmate is building the next generation savings brand, and we need a strategic, execution-focused Head of Marketing to lead the charge. You'll drive both B2C brand perception and B2B sales growth, with a core focus on building cultural relevance through strategic brand associations, amplifiable moments, and community-driven experiences. This is a high-impact role where you'll architect and drive growth across both B2C (app downloads, influencer marketing, consumer brand) and B2B (cold lead generation, community building, sales enablement) channels.

The key insight: winning consumer perception unlocks B2B success. Brands want to associate with what's trendy, exclusive, and culturally relevant. You'll turn our activations, partnerships, and community moments into high-engagement content that drives lead generation and brand equity.

This role is uniquely positioned:
Our company is transforming from just a consumer app, to a growth engine for brands. Brands can use our channels to directly speak to our users, or use our data to supplement their marketing efforts. You’ll be responsible for the strategy of growing both - no easy feat.

The ideal candidate should have either a growth marketing or product marketing background.

Location:

Remote (NYC or LA strongly preferred)

-------------------------------------------------------------

Our current strategy is often a bit scattered. A large portion of this job will be to build out a thesis and really go ham on a bi-lateral B2B/B2C strategy and work in partnership with the team to execute on that strategy.

• Develop unified marketing strategy across B2C and B2B channels.
• Create clear, simple product marketing that makes complex offerings digestible
• Stay on the pulse of cultural trends to position Checkmate as the "cool" choice in savings and marketing tech

• Generate cold leads beyond our current agency-dependent sourcing. North star is diversifying our sales funnel and bolstering direct sales vs. referrals at a low CAC.
• Create viral-worthy content from conferences, partnerships, and B2B events (Linked In, podcasts, etc.)
• Build B2B community through experiences, dinners, and thought leadership
• Develop product marketing materials (decks, videos, guides) that clearly communicate value
• Help with the overhaul of…