Job Description

Join the Legal Tech Revolution at Litera

Are you ready to shape the future of how law is practiced? At Litera, we’re on a mission to Raise The Bar™️ for the legal profession by delivering transformational and globally trusted solutions to law firms and corporate legal teams worldwide. We’ve been a leader in legal tech innovation for 30 years and are leading the legal AI revolution to this day with most of the world’s largest law firms as our clients. If you’re passionate about building AI-forward solutions that scale globally and want your work to impact millions of legal professionals worldwide, this is your opportunity to be part of an extraordinary team that’s elevating the craft of law.

As part of our strategic growth and commitment to fostering collaboration and operational excellence, we are transitioning to a hybrid working model. This position can be based in Toronto and candidates should reside within reasonable commuting distance, as this role requires on-site presence at least three days per week. This hybrid approach enables us to build a collaborative and innovative work environment while maintaining the flexibility that supports both productivity and work-life balance. We are actively seeking talented individuals to join our team in this exciting new phase of growth.

This Product Manager role sits at the heart of Litera’s strategy to modernize how contracts are drafted, negotiated, and finalized .

Role Overview

As a Product Manager focused on D ocument Comparison, you will drive the evolution of Litera’s comparison experience by transforming the user experience from an isolated d esktop application to a compa re anywhere experience that connects users into the broader Litera One cloud ecosystem . You will be accountable for meaningful business outcomes , including adoption, ret ention an d revenue impact.

Document comparison is used by nearly every lawyer to generate redlines and understand changes across documents. Your role is to ensure Litera continues to lead this category while moving customers to modern, cloud‑enabled workflows—without compromising the speed, reliability, and trust that high‑frequency users depend on.

Your success will be measured by:

• Growth in adoption of cloud‑based comparison experiences

• Sustained usage and retention of the desktop experience

• Successful migration of customers off legacy and end‑of‑life comparison solutions

• Maintained market leadership against direct redlining and comparison competitors

This role requires deep customer empathy, strong execution instincts, and a relentless focus on outcomes.

Business Outcomes You Will Drive

• In this role, you will be directly accountable for:

• Increased adoption of cloud‑based comparison capabilities , driven through enhancements to the desktop experience

• High usage and retention of the desktop comparison workflow during the transition to cloud‑powered architecture

• Successful customer migration from legacy and end‑of‑life comparison tools to modern Litera solutions

• Reduction in customer friction and migration risk through clear parity mapping and targeted enhancements

• Sustained and strengthened market leadership in document comparison and redlining

Core Product Focus

You will lead strategy and execution for Litera’s document comparison portfolio , including:

• Modernizing a desktop comparison application to be cloud‑powered while preserving performance, reliability, and trust

• Creating seamless pathways that guide users from desktop comparison into cloud‑based experiences

• Identifying and closing parity gaps between legacy comparison tools and modern Litera offerings

• Ensuring comparison workflows continue to meet the nuanced, high‑stakes needs of legal professionals

AI is an important lever in this role, applied thoughtfully to improve accuracy, performance, and confidence , without introducing unpredictability into a workflow lawyers rely on daily . Y ou will across the full product management stack ensuring deep understanding of:

The Customer – C learly articulating who our customers are and the problems they face in their workflow . You’ll engage directly with customers to learn about their needs and concerns. You’ll present and gather feedback on the roadmap . You’re skilled at synthesizing, understanding, and tracking customer data and use it to help prioritize engineering efforts.

The Competition – Be the expert on what the competition is doing as well as where the market is heading from a trends perspective. You’ll be responsible for a deep understanding of how we differentiate, but not just for difference's sake, but to support our position in the market.

The Requirements – You’ll define engineering efforts by authoring Epics and Stories that clearly define WHO the feature or experience is for, written in the user voice and WHY this effort is valuable. Clear prioritization is critical with a rolling monthly updated roadmap modified and refreshed based on the latest data and customer information.

The Story, The Vision – Everyone from engineering, QA, user experience, marketing and customer facing teams need to know what story we’re trying to tell with the work we’re doing. Not the “What” but the “Why ” it matters. A coherent vision told as a story in the user voice is critical for aligning all disciplines to the same goal.

The Roadmap – What is coming next? When is it coming? You’ll drive the beating heart of the Product Development organization. You’ll adjust the prioritization based on customer data, engineering team status and latest strategic priorities. You’ll balance short term tactical delivery-focused monthly releases with longer term strategic approaches to winning in the market. This role will have a specific focus on Kira’s path forward as AI technologies continue to advance.

The User Experience – You’ll partner with the Litera Design team to ensure the user experience is a first-class citizen in our product development efforts. While the Product Manager does not own the design direction in isolation, they must be passionate about the end user experience and advocate for the various personas.

The End-To-End – Your job is to shepherd the development of the product and to enable the Go-To-Market teams so they’re armed to tell the right story and can support our customers with confidence.

Key Responsibilities

Product Strategy & Commercial Impact

• Define and own the product vision and roadmap for document comparison

• Drive cloud adoption through enhancements to the desktop experience

• Make prioritization decisions based on adoption, migration success, and competitive impact

Adoption, Migration & Retention

• Treat migration off end‑of‑life tools as a core product outcome

• Identify parity gaps and lead efforts to close them through targeted enhancements

• Partner with Sales and Customer Success to understand blockers to adoption and churn risks

Platform & AI‑Enabled Modernization

• Lead the transition from desktop‑only comparison to a cloud‑powered architecture

• Apply AI thoughtfully to improve accuracy, performance, and usability

• Ensure reliability, trust, and predictability remain non‑negotiable standards

Competitive Leadership

• Maintain deep expertise in the document comparison market

• Drive differentiation that reinforces Litera’s leadership in redlining

• Anticipate competitive moves and adjust strategy proactively

Cross‑Functional Leadership

• Partner closely with engineering, design, and domain experts

• Communicate strategy, trade‑offs, and progress clearly to executive stakeholders

• Champion an outcome‑driven product culture focused on adoption and leadership

Qualifications

• 3+ years of product management experience owning customer‑facing workflows

• Proven ability to drive adoption and retention in high‑usage, mission‑critical products

• Experience modernizing legacy or desktop software and introducing cloud capabilities

• Strong customer research and problem‑discovery skills

• Excellent communication and stakeholder management abilities

• Experience in legal technology or document‑centric workflows is highly desirable

Why Join Litera ?

• The company culture: We emphasize helping each other grow, doing the right thing always, and being part of a journey to amplify impact, creating an exciting and fulfilling work environment

• Commitment to Employees : Our people commitment is based on what employees love most about being part of the team, focusing on tools that matter to the difference-makers in the legal world and amplifying their impact

• Global, Dynamic, and Diverse Team : Our is a global company with ambitious goals and unlimited opportunities, offering a dynamic and diverse work environment where employees can grow, listen, empathize, and problem-solve together

• Comprehensive Benefits Package: Experience peace of mind with our health insurance, retirement savings plans, generous paid time off, and a supportive work-life balance. We invest in your well-being and future, ensuring a rewarding career journey.

• Career Growth and Development : We provide career paths and opportunities for professional development, allowing employees to progress through various technical and leadership roles

#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.

Salary Range (Ontario Applicants):
This position has a base salary range of $105,000 to $140,000 CAD , with additional eligibility for a discretionary annual bonus and benefits. The final offer will depend on experience, qualifications, and internal equity.

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.

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