Director, Product Operations (Product Operating Model + Leadership)

Why this Role Matters 

As the Director, Product Operations, you’ll own the system that makes Litera’s product organization run as one. As the #2 to our VP, Engineering and Product Operations, you’ll partner closely with him to set the direction and pace for how product teams work together. This is a force multiplier role: you’ll change how ~100 people in product work by selling ideas and being the partner teams want to align with. From day one, you’ll lead the Product Operations team (weekly meetings, produce content, set the agenda) and run the operating cadence (board decks, QBRs, operational updates, etc.) where getting both the numbers and the story right shapes the decisions our board and business make. You’ll also help the organization put AI to work in Product, drive organic revenue growth, and bring go-to-market discipline to every launch.

Where You’ll Work 

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

What You’ll Deliver 

• A senior, embedded Product leader and partner to the VP of Product & Engineering Operations, who owns the system that makes a 25+ product portfolio run as one organization, with a shared tempo, shared standards, and a shared story. 

• A high-performing team, with day-one leadership of the Product Operations function (including program management, product launch, and metrics and insights), plus management and director-level staff through weekly staff meetings, agendas, and content. 

• A disciplined operating cadence that runs on time and with quality, including monthly board decks, QBRs, operational updates, and all-hands, giving leadership clear visibility and the product organization a consistent rhythm of planning, execution, and review. 

• Board- and executive-ready narratives that pair the right numbers with the right story, translating complex operational detail into clear decisions and actions for senior leadership, board members, and key stakeholders, and taking that reporting burden off the handful of people who carry it today. 

• A unified Product Playbook, the 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. 

• A mature, cross-functional go-to-market model that ensures every launch is strategically sequenced and operationally ready, and drives adoption, retention, and expansion across Litera’s portfolio. 

• Strategic roadmap alignment that connects product investment to business priorities, so sequencing is clear, decisions are traceable, and teams move with intent. 

• A product organization focused on organic revenue growth, coaching PMs to think about how to monetize what they build, and to frame, price, and invest in it the right way. 

• Practical AI adoption across the product function, including evaluating and implementing capabilities (such as automated PRDs and AI-driven product discovery) that improve collaboration, forecasting, and execution, and partnering with the team leading the AI mandate and Playbook refresh. 

• 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. 

• Influence without direct authority across a ~100-person product organization, earning alignment through partnership, credibility, and clear thinking, so that best practices become the default and accountability is built in. 

What You’ll Bring 

Must-Haves

• 10+ years in Product Operations, Product Management, or Program Management within technology or SaaS organizations 

• Significant tenure at the Director level or above, with a track record operating at that level 

• Proven experience building and scaling product operating models, playbooks, and planning cadences across complex, multi-product portfolios 

• Deep, hands-on understanding of how operations works inside product, including the metrics, cadence, and reporting that boards and executive teams rely on 

• Experience building board- and executive-level narratives, with a clear grasp of story versus content, and polished presentation skills (e.g., QBRs, board decks) 

• Track record of leading cross-functional programs and influencing senior stakeholders across product, engineering, UX, customer success, and go-to-market 

• Ability to command a room of strong personalities, with the confidence to lead and the humility to partner 

• Experience in at least one (ideally more) of the following:  

• Leading AI programs and adoption within product management 

• Driving a product organization focused on organic revenue growth, with working knowledge of financial modeling and pricing 

• Leading or deeply partnering with a mature GTM function, and able to speak in depth about what “good” looks like 

• Highly organized, with the discipline to run a recurring operational cadence 

• 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 

• Experience in PE- or VC-backed B2B SaaS companies 

• Background in product management, agile coaching, or UX operations 

• Experience leading change management and scaling organizations through high-growth phases, including integrating acquired products and teams 

• Certification in Agile, Scrum, or program/project management 

Great candidates don’t check every box. If this role excites you, we encourage you to apply. 

What You’ll Experience 

• A team that shows up. Work alongside people who collaborate, support one another, and lead with integrity. 

• Global Reach. Partner with teams around the world to solve complex challenges that matter. 

• Real opportunity for growth. Expand your impact through meaningful stretch opportunities, visibility and career development. 

• AI-driven innovation. Work at the intersection of legal technology, customer outcomes, and cutting-edge AI. 

Pay Transparency for Ontario Applicants 

The base salary range for this role is $125,000 to $150,000 CAD. Final compensation will be determined based on experience, skills, education, and other relevant qualifications. This role is also eligible to earn commission based on performance. In addition to base salary, 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.

Pay Transparency for Colorado Applicants 

The base salary range for this role is $160,000 USD. Final compensation will be determined based on experience, skills, education, and other relevant qualifications. This role is also eligible to participate in a company bonus plan. In addition to base salary, Litera offers a comprehensive benefits package, including medical, dental, and vision coverage, a 401(k) with company match, and incentive and recognition programs. Benefits are subject to eligibility requirements.

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