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.

About The

RoleWe’re looking for an Engineering Manager to lead the team that builds, deploys and customizes Spellbook for our enterprise customers. You’ll own engineering’s side of enterprise: what we build, what we defer, and how we design the solutions. This is a hybrid of engineering manager and technical program lead.

You’ll manage and grow a team of backend, full-stack, and forward-deployed engineers. Enterprise work is tactical and technical. Large deals bring urgent asks, integrations and customization requirements, and data residency needs.

Many deals are won with a working prototype in front of the customer, so you’ll lead pre-sales prototyping: deciding what to demo, building it fast, and knowing when a prototype should become product. You’ll be the one who gives the team direction, judgment, and momentum. Turn customer asks and roadmap bets into a prioritized plan with clear owners, milestones, and risks.Decide which ones are worth building, keep them time-boxed, and turn the winners into production plans or reusable product capabilities.Set a high bar for performance without adding unnecessary process.Manage dependencies with Core, ACM, and Platform, and surface blockers early.Stay technical.

Review designs and critical code, prototype when it helps, and step in on the hardest problems.Partner with product,



design, and customer success to decide what to build and to feed what we learn from deployments back into the core product.Raise the team’s AI velocity. Adopt coding agents and automated review where they improve speed or quality, and define practical standards for quality and reliability. Qualifications5+ years of software development experience, including technical leadership in a startup, scale-up, or other fast-moving environment.Experience leading engineers and owning delivery of production software.Experience working with sales or customer-facing teams on enterprise deals: scoping, technical due diligence, demos, security and procurement reviews, integrations.A record of prioritizing ruthlessly, making tradeoffs transparent, pushing back constructively on sales or customers when needed, and making good calls without waiting for direction.You can turn ambiguous customer asks into focused plans and shipped results.Robust system design and backend or full-stack skillsRegular use of coding agents or similar AI tools, with concrete examples of improving speed or quality.Clear communicator who aligns engineering, sales, product, and customers around tradeoffs.

Nice to havesExperience with enterprise SaaS deployments, integrations (DMS, CRM, procurement systems), or forward deployed / solutions engineering teams.Experience with security and compliance (SOC 2, data residency,



enterprise procurement).Experience building LLM-based products or agent workflows.Experience leading rapid prototyping or proof-of-concept work for prospects, including with coding agents.Technical program management experience.Legal tech or document-heavy workflow experience.WHY JOIN SPELLBOOKEmbrace autonomy and accountability in a flexible work environment; we focus on outcomes and empower you to determine how to get the job doneAccess our company-paid group benefits for you and your family, with $1,000 towards mental health supportDisconnect during our holiday closure and take advantage of our generous time off policies throughout the yearEnjoy monthly paid meals, an annual wellness allowance to support your well-being and parental leave top-ups as your family growsSecure your stake in our success; We do not discriminate based on gender, race, religion, national origin, ethnicity, disability, gender identity/expression, sexual orientation, veteran or military status, or any other protected category. Use of Artificial Intelligence in RecruitmentSpellbook uses artificial intelligence (AI) responsibly to support administrative and efficiency-focused aspects of our recruitment process. This includes activities such as drafting job descriptions, generating interview questions, note-taking and recordings, and supporting sourcing and scheduling workflows.

While AI tools may assist with screening and assessment, they do not replace human judgment in selection decisions. Our use of AI is intended to streamline routine tasks, improve consistency, and enhance the overall candidate experience.

Our Compensation

PhilosophySpellbook uses industry benchmark data to establish compensation bands for all roles. In addition to base salary and applicable commissions, total rewards may include equity, health and wellness benefits, and other company programs.

📌 Software Engineering Manager, Enterprise (Winnipeg)
🏢 Spellbook
📍 Winnipeg