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.

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.

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About the Role

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)

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What You'll Own

Strategic Marketing 🎯

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

B2B Marketing & Lead Generation 💼

• 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 (LinkedIn, 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 our website to better align with the B2B/B2C strategy you set
• Support sales, partnerships, and customer success with quality lead gen

B2C Brand Building ⚡

• Execute social media strategy focused on amplifiable moments - own the conversation. North star is growing MAU MoM
• Develop TikTok strategy around savings hacks and relatable content
• Turn UGC, influencer partnerships, and power users into compelling ads and organic reach
• Design community moments (events, giveaways, surprise and delight) that create content opportunities
• Build relationships with trending brands and influencers

Product Marketing 💡

• Simplify and unify how we explain our products - make complex offerings clear and accessible
• Bridge the gap between our consumer savings narrative and B2B marketing platform positioning
• Develop product marketing materials (decks, videos, guides, website content) that clearly communicate value across all customer segments and are consistent across all touchpoints 
• Own the product narrative so brands and consumers quickly understand what Checkmate does and why it matters

Community Building 🌟

We've built momentum with events that generate LinkedIn buzz and drive real business outcomes. Now we're scaling to the next level: building a comprehensive ecosystem for ecommerce brands where community becomes our competitive moat.

You won't build every event yourself, but you'll ensure every activation drives maximum impact:

• Cold lead gen events with influencers that draw brands into our ecosystem
• Curated experiences and dinners to close warm leads and upsell customers
• Turn in-person moments into viral online engagement
• Scale from individual activations to a must-attend community ecosystem
• KPIs: deals sourced, deals closed, upsells, social engagement

Success Metrics 📈

• Cold B2B lead generation through marketing initiatives
• Deals closed and upsold from marketing touchpoints
• Brand perception as culturally relevant and performance-driven
• Social media reach, engagement, and viral moments
• Simplified, unified product narrative, with an easy to understand website and supplemental sales assets that can scale a growth team

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Experience:

• 5-8 years in growth marketing or product marketing at software/SaaS startups
• Second-in-command experience (reporting to a CMO/SVP/VP as a Marketing Director, Head of Growth, etc.) with proven execution ability
• Ecommerce tech or B2B/B2C hybrid background preferred
• Track record of building brand while driving measurable outcomes

Skills:

• Strategic but hands-on: you’re a doer, not just a delegator
• Culturally tuned-in with pulse on trends and what makes brands "cool"
• Content creator mindset that turns moments into amplifiable content
• Data-driven with ability to set KPIs and optimize
• Product marketing expertise: you excel at distilling complexity into simplicity
• High social EQ: you know how to build meaningful relationships before selling
• Growth marketer mentality: you’ve done a bit of everything and know how to prioritize

What "Cool" Means: Association with trending brands and respected people, elevated exclusive experiences, on-trend opinions, relationship-building over hard selling, and smart positioning with marketing expertise.

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

Checkmate Values:

1. Ownership – Radical Ownership, High Standards & Pride in Work

We believe in radical ownership, where every team member takes full responsibility—not just for tasks, but for outcomes. This means deeply caring about your work product, ensuring it meets the highest standards, and recognizing its impact on the organization as a whole. We expect our team to take a macro approach, proactively identifying opportunities for improvement, solving problems, and driving results. Ownership means accountability—you own what success looks like and take pride in delivering exceptional work.

2. Data-Driven – Performance-Oriented, Work Smarter, Own Success

We are a performance-driven organization that makes strategic decisions based on data, KPIs, and impact. We believe in working smarter, not just harder, leveraging insights and efficiencies to drive results. Success isn’t just an abstract goal—it’s something you own, define, and deliver. Every action should tie back to the bigger picture, ensuring alignment with our company’s mission and objectives.

3. Grit – Hustle, Adaptability & Resilience

Grit is about the relentless pursuit of outcomes and solutions. We embrace hustle, adaptability, and resilience—pushing through obstacles, staying agile in the face of change, and continuously iterating to improve. Challenges aren’t roadblocks; they’re opportunities to grow, learn, and execute better. We get things done and take pride in seeing tough problems through to resolution.

4. People Matter – Respect, Teamwork & Continuous Learning

We believe in being a team player—supporting each other, communicating effectively, and always striving to learn and grow. Respect for your peers is non-negotiable; strong collaboration and trust lead to stronger outcomes. We challenge each other to improve, share knowledge, and work together to achieve success. Great teams aren’t just built on talent—they’re built on respect, effort, and commitment to shared goals.