Director of Product Marketing

Checkbox Technology • New York, NY

33d • Hybrid

About The Position

Checkbox is a VC backed technology start-up with a mission to enable meaningful work for all. We are building an AI-first platform that is transforming how in-house legal teams operate, from how work enters legal through to how it is managed, delivered, and resolved.
Having very recently announced our Series A, we are entering a critical scale-up phase focused on deepening our product, accelerating go-to-market execution, and establishing category leadership in legal technology. Our customers include sophisticated in-house legal teams at companies such as SAP, Coca-Cola, Allianz, and Disney.
More recently, we launched our AI-powered Intake and Matter Management product, often described as the “JIRA for lawyers”. This is part of our broader vision to become the AI Legal Front Door inside organisations, acting as the system of record for legal demand, delivery, and outcomes.
We are a tight-knit, high-performing team across the United States, Australia, and Asia, including founders recognised in the Forbes 30 Under 30 list. Our culture is built on trust, ownership, and a strong bias for impact.
We are hiring a Director of Product Marketing to build, own, and lead Product Marketing end to end at Checkbox.
This is the first Product Marketing hire and the clear owner of the function. Reporting to the VP of Marketing and operating as a peer to the Director of Brand, you will define how our AI-powered platform is positioned, launched, and sold.
You will sit at the intersection of Product, Sales, Marketing, and Customer teams, shaping our narrative, influencing roadmap decisions, and ensuring our AI capabilities translate into real customer value and measurable revenue impact. This role is both strategic and hands-on, with a mandate to build the foundations of Product Marketing as we scale beyond Series A.

Requirements

• 8 to 12+ years of Product Marketing experience in high-growth B2B SaaS environments
• Experience operating as the first or sole Product Marketing owner is strongly preferred
• Proven ability to define positioning, lead go-to-market strategy, and drive measurable revenue impact
• Strong understanding of AI-powered products and how to position them responsibly and credibly
• Exceptional communicator who can align executives, product teams, and revenue teams around a shared narrative
• Comfortable operating with ambiguity, ownership, and pace in a Series A environment
• Strategic thinker who is equally willing to execute hands-on when needed

Responsibilities

• Product Positioning, Messaging and AI Narrative
• Own the product marketing strategy and positioning for our AI-driven platform
• Define and evolve the product narrative, clearly articulating AI capabilities, differentiation, and customer outcomes
• Translate complex technical and AI concepts into clear, credible value propositions for legal buyers
• Ensure consistent messaging across launches, website, sales materials, and lifecycle campaigns
• Go-to-Market and Revenue Enablement
• Lead go-to-market strategy in close partnership with Product, Sales, and Marketing leadership
• Own product launches aligned to the roadmap
• Build and scale sales and partner enablement, including pitch decks, narratives, battlecards, ROI frameworks, and competitive positioning
• Improve sales onboarding, deal quality, win rates, and expansion conversations
• Market Intelligence and Strategic Insight
• Own voice-of-customer programs including interviews, win and loss analysis, and usage insights
• Build a deep understanding of the competitive landscape, buyer personas, and AI adoption trends within legal
• Use market insight to inform product strategy, packaging, pricing, and go-to-market priorities
• Function Ownership
• Establish Product Marketing as a first-class function
• Define playbooks, operating rhythms, and standards that scale with the business
• Act as the senior Product Marketing voice across Product, Sales, Marketing, and Customer teams

Benefits

• Competitive salary and meaningful equity with a strong belief in employee ownership
• Hybrid working model with time in our New York City office alongside flexibility
• Personal learning and development budget to support continuous growth
• Flexible leave policy with a culture that genuinely supports taking time off
• Expense policy and reasonable salary sacrifice options
• Regular team events and company-wide offsites that bring our global team together
• An open, transparent culture where feedback is welcomed and ideas are valued

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 11-50 employees