Head of Marketing

Checkmate • Full-time • Remote • 3w ago

About Checkmate 🛍 📲

Checkmate is the AI-powered savings app that 5M+ shoppers use to get personalized deals at 100K+ stores. 1.5M followers on TikTok and Instagram. 250K+ emails and notifications sent every single day. 450+ brands pay us for performance. Backed by GV, Mantis VC, and DST Global. Series A. Growing fast.

We're not a coupon site. We're building the savings brand for the next generation of online shoppers, and the performance platform every eCommerce brand wants to be part of.

The Opportunity 🎯

5M shoppers. 1.5M social followers. 250K+ daily touchpoints. A product people love. And we're just getting started.

We need someone who can feel the pulse of what shoppers want, move faster than the market, and turn Checkmate into the brand everyone's talking about. Then take that heat and make 450+ brand partners feel like they'd be crazy not to be part of it.

This is a rocketship role. We're scaling quickly and you'll have enormous reach from day one.

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About the Role

Head of Marketing. Own Checkmate's consumer brand and growth (~70%), with a secondary focus on turning that momentum into B2B demand (~30%).

You'll have 250K+ daily emails and notifications flowing to shoppers across Checkmate's app and desktop experience. That's your engine. Your job is to make every one of those touchpoints count, grow the shopper base, build cultural relevance, and make brands desperate to be part of the ecosystem.

Reports to the CEO.
Location: Remote (NYC, LA, or other major city strongly preferred)

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What You'll Own Consumer Brand & Growth 🌟

Grow monthly active shoppers. This is the north star.
Own 250K+ daily emails and notifications. Optimize the funnel from notification to app to conversion. This is a massive channel and it's yours.
Build Checkmate into the savings brand people actually talk about. Not Honey. Not a coupon site. Something shoppers are proud to use.
Run social (TikTok, Instagram) and grow our 1.5M following with a content engine built around amplifiable moments.
Develop influencer and creator partnerships that drive real downloads, not vanity metrics.
Turn UGC, power users, and viral moments into compelling organic and paid creative.
Stay ahead of culture. Know what shoppers want before they know. Position Checkmate where saving money meets being smart about it.

B2B Demand (Secondary) ⚡

Package consumer momentum for brands. 5M shoppers choosing Checkmate is a story. Tell it.
Generate inbound interest through content, events, thought leadership, and social proof.
Build B2B community through curated experiences and events that turn warm leads into partners.
Support sales with product marketing materials that clearly communicate value.
Help overhaul the website to tell both the consumer and brand story.

Product Marketing 💡

Simplify how we explain Checkmate. Make complex offerings clear for shoppers and brands.
Own the product narrative. One consistent, compelling story across every touchpoint.

Success Metrics 📈

Monthly active shopper growth (MoM)
App downloads and extension installs
Email/notification engagement and conversion
Social media reach, engagement, and viral moments
B2B leads sourced through marketing
Deals influenced by marketing touchpoints

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Experience:

5-8+ years in growth or brand marketing at a consumer tech / B2C startup
Track record of building a consumer brand people care about, not just running campaigns
Experience scaling social/content channels with measurable growth impact
Bonus: hybrid B2C/B2B or eCommerce background
Second-in-command experience (reported to CMO, VP Marketing, or founder) with proven execution

Skills:

Strategic but hands-on. You're a doer, not a delegator.
Culturally tuned-in. You know what's trending before it trends.
Content-native. You think in social-first formats and turn moments into content.
Data-driven. You set KPIs, track them, and optimize relentlessly.
Product marketing chops. You distill complexity into simplicity.
High social EQ. You build real relationships, not transactional ones.
Scrappy. You've done a bit of everything and know how to prioritize.

Competitive salary + equity

Healthcare + dental + vision
401(k)
4 weeks PTO + health days
Gym membership reimbursement
US Remote-friendly, with remote hubs in NYC and LA
Regular offsites and team retreats

Checkmate Values:Ownership. You own outcomes, not just tasks.Data-Driven. Every action ties back to the bigger picture.Grit. Challenges are opportunities. We get things done.People Matter. Great teams are built on trust, effort, and commitment.