Director, Product Operations

Litera•Toronto, ON

2d•CA$190,000 - CA$219,000•Hybrid

About The Position

The Director of Product Operations is a senior leader responsible for the operational backbone of a complex, fast-growing portfolio of legal technology solutions. Reporting into product leadership, this role sets the operating model for how the product organization plans, executes, and learns while partnering with product management, engineering, UX, data, marketing, and go-to-market leaders to translate strategy into a repeatable, high-performing rhythm. This is a high-influence leadership role for someone who can build durable systems and raise the operational bar across the entire product function.

Requirements

10+ years in Product Operations, Product Management, or Program Management within technology or SaaS organizations, including 3+ years leading teams or programs at scale.
Proven experience building and scaling product operating models, playbooks, and planning cadences across complex, multi-product portfolios.
Track record of leading cross-functional programs and influencing senior stakeholders across product, engineering, UX, customer success, and go-to-market.
Strong analytical and systems-thinking skills — able to synthesize data, design frameworks, and drive measurable operational improvement.
Exceptional executive communication and presentation skills — able to craft compelling narratives and translate operational complexity into clear decisions and action.
Advanced proficiency with product lifecycle and analytics tools such as Jira, Confluence, and Pendo.

Nice To Haves

Experience in legal technology, compliance, or other regulated industries.
Background in product management, agile coaching, or UX operations.
Experience leading change management and scaling organizations through high-growth phases.
Certification in Agile, Scrum, or program/project management.

Responsibilities

Develop and implement a mature, cross-functional go-to-market model that ensures every product launch is strategically sequenced, operationally ready, and set up to drive adoption, retention, and expansion across Litera’s portfolio.
Create and maintain a unified Product Playbook — the definitive, living standard for how Litera’s product teams roadmap, discover, plan, and launch — continuously refined and embedded into tools and onboarding so quality scales with the organization.
Establish and manage a high-performing operating cadence that creates a disciplined, recurring rhythm of planning, execution, and review, giving leadership clear visibility and the product organization a shared tempo.
Ensure strategic roadmap alignment that connects product investment to business priorities, ensuring sequencing is clear, decisions are traceable, and the organization moves with intent.
Provide data-driven insights and reporting that give senior leaders the visibility they need to make confident decisions on resource allocation, delivery health, and portfolio performance.
Foster an enabled, high-velocity product organization through coaching, governance, and tooling, where best practices are the default, accountability is built in, and teams consistently raise their bar.
Evaluate and adopt AI-enabled capabilities that meaningfully improve collaboration, forecasting, and execution across the product function.
Develop executive-ready narratives and communications that translate complex operational detail into clear decisions and actions for senior leadership, board members, and key stakeholders.