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Spellbook

Director of Product

RemoteCanada only
Published
Role
Product
Experience
Lead
Employment
Full-time
Company size
Startup
Salary not disclosed
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Open to CA only. Set where you work from to check your eligibility.

No BS summary

We're looking for a Director of Product to own the entire product function at Spellbook. This is a high-leverage, high-ownership role: you'll set the vision for our product portfolio, lead and grow a small team of Product Managers, drive roadmap and execution, and be the connective tissue between engineering, design, GTM, and the customer. You'll report directly to the CEO and operate as a key voice in company strategy. This is not a comfort-zone role. The right person thrives in ambiguity, has sharp product instincts, and knows how to turn big bets into shipped products.

Optional skills

LLM product patterns: prompt design, retrieval-augmented generation, agentic workflows, evaluation frameworksprompt designretrieval-augmented generationagentic workflowsevaluation frameworks

What you'll do

  • Define and champion a unified product vision across Spellbook's entire portfolio - from the core Word experience to Associate, playbooks, and beyond.
  • Build, manage, and mentor a small team of PMs, creating the culture, processes, and craft that great product teams are built on.
  • Own the roadmap end-to-end - prioritization, sequencing, trade-offs - balancing near-term customer value against long-term platform bets.
  • Partner with engineering and design to drive execution: clear specs, tight feedback loops, unblocked teams, and launches that land.
  • Lead go-to-market coordination for product launches, working with marketing, sales, and customer success to ensure every release drives adoption.
  • Be the voice of the customer: synthesize insights from user research, support tickets, sales calls, and data into product decisions.
  • Partner with the CEO and leadership team on product strategy and company direction, contributing to investor narratives and fundraising materials.
  • Establish metrics and feedback loops that measure product health, feature adoption, and user outcomes across the portfolio.
  • Support with other responsibilities and projects as required.

What they require

  • You've led product at a high-growth B2B SaaS company (Series A–C), ideally in a vertical AI, legaltech, or professional-services context.
  • You have experience managing PMs - you know how to hire for craft, give feedback that grows people, and hold a high bar without micromanaging.
  • You think in systems: you can hold the big picture (portfolio strategy) and the detail (user flow, edge case) simultaneously and switch fluidly between them.
  • You've shipped products that matter - you can point to launches you drove end-to-end and explain what made them succeed or what you'd do differently.
  • You're deeply curious about AI and what's possible: you follow model capabilities, you understand what agents can and can't do, and you can separate hype from real leverage.
  • You're a strong communicator. You can write a crisp PRD, present a roadmap to the board, and have a hard conversation with an engineer about scope - all in the same day.
  • You operate with urgency and calm: you know the difference between a fire that needs putting out and noise that should be ignored.
  • Background in or adjacent to law, legal operations, or enterprise compliance workflows.
  • Experience building products that live inside third-party surfaces (e.g. Microsoft Office, Google Workspace, Salesforce).
  • Experience at a company that went through a Series B and navigated rapid scaling - or that made strategic acquisitions.
  • Preferred: Background in or adjacent to law, legal operations, or enterprise compliance workflows.
  • Preferred: Experience building products that live inside third-party surfaces (e.g. Microsoft Office, Google Workspace, Salesforce).
  • Preferred: Experience at a company that went through a Series B and navigated rapid scaling - or that made strategic acquisitions.

Benefits

  • Embrace autonomy and accountability in a flexible work environment; we focus on outcomes and empower you to determine how to get the job done
  • Access our company-paid group benefits for you and your family, with $1,000 towards mental health support
  • Disconnect during our holiday closure and take advantage of our generous time off policies throughout the year
  • Enjoy monthly paid meals, an annual wellness allowance to support your well-being and parental leave top-ups as your family grows
  • Secure your stake in our success; you’ll receive competitive stock option grants as a pivotal early employee

Spellbook is the most comprehensive AI copilot for transactional lawyers. It works directly inside Microsoft Word to help legal teams draft, review, and negotiate contracts up to 10x faster and with greater precision. Today, more than 4,000 law firms, in-house teams, and solo practitioners rely on Spellbook to simplify their workflows and eliminate the drudgery of everyday contract work. We are backed by leading investors including Khosla Ventures, Thomson Reuters Ventures, Inovia Capital, The LegalTech Fund, Bling Capital, and Moxxie Ventures. The company recently raised $50 million in Series B funding, led by Keith Rabois at Khosla Ventures, bringing its total funding to more than $80 million.*This is an existing vacancy

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