Senior Director, Product Management – Lito Platform

Job Description

Where You’ll Work

This is a hybrid role based in Toronto with the expectations to be in office at least 3 days a week for collaboration and connection.

Why this Role Matters  

As a Senior Director, 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.

What You’ll Deliver 

Product Strategy and Leadership

• Define and own the long-term product vision and strategy for Lito, Litera’s GenAI platform and 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 Expertise

• Bring 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 Insight

• Engage 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 Impact

• Partner 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 Execution

• Lead and develop a team of product managers across the Lito platform

• Foster strong collaboration with engineering, design, data, and AI teams

• Empower your 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 Influence

• Communicate 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

What You’ll Bring 

• Significant 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

• Strong 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

Pay Transparency for Ontario Applicants 
This position has a base salary range of $200,000 to $225,000 CAD. Final compensation will be determined based on experience, skills, education, and other relevant qualifications. In addition to base salary, there is additional eligibility for a discretionary annual bonus. Litera offers a comprehensive benefits package, including medical, dental, and vision coverage, retirement savings plan with company match, and incentive and recognition programs. Benefits are subject to eligibility requirements.

#LI-Hybrid

Litera is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Vacancy Status Disclosure: This job posting is for an existing job vacancy.

Litera may use artificial intelligence and automated tools as part of the recruitment and hiring process to support activities such as resume review, candidate matching, and workflow efficiency. These tools are designed to assist, not replace, human decision-making. All hiring decisions are ultimately made by qualified Litera professionals.