Job DescriptionJoin the Legal Tech Revolution at Litera. Litera is on a mission to Raise The Bar™ for the legal profession by delivering transformational, trusted solutions to law firms and corporate legal teams worldwide. As a leader in legal technology and AI innovation, Litera helps legal professionals work more efficiently, reduce risk, and deliver better outcomes for their clients.Location & Work ModelThis position can be based in Toronto, Canada; Austin, Boston, Chicago, Denver, New Jersey, New York City, Philadelphia, Raleigh, or London, UK. Candidates should reside within reasonable commuting distance, as this role requires on‑site presence at least three days per week. The hybrid approach enables us to build a collaborative and innovative work environment while maintaining the flexibility that supports both productivity and work‑life balance.OverviewAs a Senior Director of Product Management at Litera, you will be part of a dynamic team that is passionate about driving innovation in the legal technology space. You will have the opportunity to work with cutting‑edge tools and collaborate with industry experts to deliver solutions that make a real difference in the legal profession. The Senior Director, Product for Lito & Platform is responsible for setting and executing the product strategy for Lito – Litera’s GenAI platform. This role owns the evolution of Lito from a chat‑based agent into a Litera‑wide AI intelligence layer that supercharges every legal and business workflow across the Litera product ecosystem. Lito is not simply a feature; it is the platform thatwill connect and amplify Litera’s entire suite of solutions, from document drafting and redlining to matter management, firm intelligence, and beyond.Key ResponsibilitiesProduct Strategy and LeadershipDefine and own the long‑term product vision and strategy for Lito, Litera’s GenAI platform, AI intelligence layer, and the Litera One Web experience.Translate firm‑level business needs into a clear, prioritized roadmap aligned with Litera’s platform direction.Drive platform thinking across products, ensuring Lito delivers consistent, scalable integration across all Litera workflows.Identify market opportunities and shape product roadmaps for competitive advantage in the legal AI space.Leverage generative AI and LLM capabilities to deliver meaningful workflow automation and intelligence, not just chat interfaces.Balance near‑term customer value with long‑term architectural and platform investments.Optimize the Product Management Machine to empower your team.AI and Platform ExpertiseBring deep expertise in generative AI and Large Language Model (LLM) technologies,



including hands‑on experience shipping AI‑powered products to enterprise customers.Think at both the platform level (architecture, integrations, shared services) and the workflow level (user tasks, friction points, adoption drivers).Drive the evolution of Lito as an ecosystem platform, ensuring interoperability across Litera’s suite of legal tools.Stay ahead of the AI landscape to ensure Lito maintains a differentiated and forward‑looking product position.Partner with Engineering, Design, and AI/ML teams to ensure high‑quality, reliable, and performant AI experiences.Legal Industry Expertise (A Plus)Bring strong understanding of how law firms operate across practice management, document workflows, matter management, and business development.Understand how legal professionals evaluate, buy, implement, and adopt AI‑powered software, including change management and adoption dynamics.Act as a trusted product advisor to law firm partners, CIOs, legal operations leaders, and end users.Translate firm strategy, competitive pressures, and regulatory or compliance needs into AI product direction.Customer Engagement and Market InsightEngage directly with customers to validate problems, test concepts, and refine AI solutions.Build strong relationships with key enterprise clients and strategic partners.Represent Lito and Litera One Web in customer briefings, roadmap discussions, and industry forums.Use data, customer feedback, and competitive analysis to continuously guide product decisions.Go‑to‑Market and Commercial ImpactPartner closely with product marketing, sales, customer success, and professional services to shape go‑to‑market strategies for Lito.Drive go‑to‑market strategies including pricing, positioning, and sales enablement.Influence packaging and positioning decisions for Lito’s AI capabilities across the Litera ecosystem.Support sales and account teams with clear product narratives and value articulation.Monitor market trends and the competitive AI landscape to inform product decisions.Cross‑Functional Leadership and ExecutionLead and develop a team of product managers across the Lito platform.Foster strong collaboration with engineering, design, data,



and AI teams.Empower product managers to lead cross‑functional teams through product development cycles and successful launches.Ensure high‑quality delivery through clear priorities, strong execution discipline, and customer validation.Remove obstacles and resolve cross‑team dependencies to keep work moving forward.Executive Communication and InfluenceCommunicate product vision, priorities, and progress clearly to executive leadership.Present product strategies and updates to executives and board members.Connect product strategy to business outcomes in a clear and compelling way.Influence without authority across senior stakeholders and partner teams.Help shape broader company AI strategy through insight‑driven product leadership.QualificationsSignificant experience in product leadership roles within B2B SaaS, enterprise software, or legal technology.Demonstrable expertise with generative AI and Large Language Model (LLM) technologies, including experience shipping AI‑powered products to enterprise customers.Proven track record of defining and executing product strategy that spans multiple product lines or user personas.Exceptional ability to think at both the platform level (architecture, integrations, shared services) and the workflow level (user tasks, friction points, adoption drivers).Demonstrated ability to lead platform products and AI‑driven solutions at scale.Proven track record of delivering products from concept to market adoption.Robust people‑leadership skills with experience building and mentoring product teams.Exceptional communication skills with the ability to engage both technical and non‑technical audiences.Experience in the legal technology market or a closely related professional services industry strongly preferred.Experience working within a Microsoft 365 / Azure ecosystem is a plus.Advanced degrees such as MBA, JD, or equivalent experience is a plus.Benefits & CultureCompany culture focuses on growth, integrity, and making an impact.Commitment to employees with emphasis on well‑being, including health insurance, retirement savings plans, generous paid time off, and supportive work‑life balance.Diverse, dynamic, and inclusive team worldwide.Career growth and development opportunities across technical and leadership tracks.Comprehensive benefits package, incentive and recognition programs, and 401(k) contribution (subject to eligibility).Salary RangeOntario applicants: $200,000 – $225,000 CAD (base salary) with discretionary annual bonus eligibility.United States applicants: $145,000 – $165,000 (US dollars).Equal Opportunity EmploymentLitera is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.Vacancy StatusThis job posting is for an existing job vacancy.#J-18808-Ljbffr

📌 Senior Director, Product Management - Lito Platform - $145,000 - $225,000 A Year (Winnipeg)
🏢 Litera
📍 Winnipeg