Remote Product Operations Analyst Jobs in Ontario

Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely.

We are transforming the legal experience for all by bettering the lives of legal professionals while increasing access to justice.

We are seeking a Senior R&D Operations Specialist to help scale the operating systems, planning rhythms, and cross-functional coordination that enable Clio's Product, Design, Engineering, and Research teams to do their best work. This role is available to candidates across the United States or Canada (excluding Quebec) in a remote capacity. If you are local to one of our hubs (Burnaby, Calgary, or Toronto) you will be expected to be in office minimum two days per week for our Anchor Days.

This role will sit within R&D Operations and work closely with leaders across Clio Work, Enterprise, and related product areas to bring greater clarity, consistency, and momentum to complex, cross-functional work. You'll help create the shared information layer that keeps teams aligned on where we're going, why it matters, what success looks like, and how we're progressing.

This is not a purely logistical role. We are looking for someone who is deeply organized and detail-oriented, but also curious about product strategy, customer value, business outcomes, and how teams work together. The right person will reduce friction, improve visibility, strengthen follow-through, and help teams coordinate horizontally across initiatives with less chaos and more impact.

• Build and maintain clear sources of truth for portfolio priorities, milestones, dependencies, owners, decisions, risks, and progress.

• Strengthen the operating rhythms that help teams stay aligned, including planning cadences, leadership syncs, showcases, QBRs, all hands, and cross-functional forums.

• Create and manage workback plans for complex product initiatives, helping teams clarify milestones, dependencies, decision points, success measures, and follow-through.

• Improve horizontal coordination across Product, Design, Engineering, Research, GTM, Data, and other cross-functional partners, ensuring the right people are in the right conversations at the right time.

• Support the development, communication, and tracking of quarterly and annual OKRs, ensuring goals and metrics connect clearly across portfolios and teams.

• Partner with Strategy & Ops, Data, and GTM teams to bring product usage, customer, revenue, and market signals into regular R&D operating rhythms.

• Create lightweight templates, documentation, dashboards, and playbooks that reduce duplication, improve clarity, and help teams work together more effectively.

• 5+ years of experience in product operations, R&D operations, program management, business operations, strategy and operations, or a related role in a technology environment.

• Strong program management skills, with experience coordinating complex initiatives across multiple teams, leaders, and stakeholders.

• Excellent organizational skills, with a proven ability to create clarity, maintain follow-through, and ensure important details do not fall through the cracks.

• Strong communication and stakeholder management skills, with the ability to build trust and influence across senior leaders and cross-functional partners.

• Comfort navigating ambiguity and bringing structure to complex, evolving systems without creating unnecessary overhead.

• Strong analytical skills, with the ability to synthesize product, customer, operational, and business data into clear insights and recommendations.

• Experience or strong curiosity in using AI to increase operational leverage, including synthesizing information, improving workflows, reducing administrative burden, and helping teams move faster with more clarity.

• You are a systems thinker who can see how people, processes, tools, data, and communication patterns connect.

• You are highly organized and detail-oriented, but not rigid. You create structure that helps teams move faster, not slower.

• You are proactive about spotting gaps, risks, unclear ownership, duplicated work, and misalignment before they become bigger problems.

• You are comfortable asking thoughtful questions when goals, metrics, narratives, or decisions do not seem to connect.

• You can translate strategic direction into operating rhythms, workback plans, dashboards, communication artifacts, and clear next steps.

• You build trust quickly by being reliable, clear, thoughtful, and pragmatic.

• You look for thoughtful ways to use AI to simplify workflows, synthesize information, and reduce administrative burden for the teams you support.

• Experience supporting multi-product SaaS, enterprise software, or platform teams.

• Experience supporting annual planning, quarterly planning, QBRs, roadmap reviews, or executive operating rhythms.

• Experience creating dashboards, scorecards, or reporting mechanisms that inform leadership decisions.

• Experience working with product analytics, customer feedback systems, NPS, UMUX, revenue data, or customer insight programs.

• Experience supporting internal communications, leadership forums, or enablement programs for technical teams.

• Experience supporting change management or operational transformation in a growing R&D organization.

If you're excited about transforming how lawyers deliver legal services and want to help build the operating foundation that enables Product, Design, Engineering, and Research teams to deliver meaningful impact at scale, we'd love to hear from you.

What you will find here:

Compensation is one of the main components of Clio's Total Rewards Program. We have developed a series of programs and processes to ensure we are creating fair and competitive pay practices that form the foundation of our human and high-performing culture.

Some highlights of our Total Rewards program include:

• Competitive, equitable salary with top-tier health benefits, dental, and vision insurance

• Hybrid work environment, with expectation for local Clions (Vancouver, Calgary, Toronto, Dublin, London, New York City and Sydney) to be in office min. twice per week.

• Flexible time off policy, with an encouraged 20 days off per year.

• $2000 annual counseling benefit

• RRSP matching and RESP contribution

• Clioversary recognition program with special acknowledgement at 3, 5, 7, and 10 years

Diversity, Inclusion, Belonging and Equity (DIBE) & Accessibility

Our team shows up as their authentic selves, and are united by our mission. We are dedicated todiversity, equity and inclusion. We pride ourselves in building and fostering an environment where our teams feel included, valued, and enabled to do the best work of their careers, wherever they choose to log in from. We believe that different perspectives, skills, backgrounds, and experiences result in higher-performing teams and better innovation. We are committed to equal employment and we encourage candidates from all backgrounds to apply.

Clio provides accessibility accommodations during the recruitment process. Should you require any accommodation, please let us know and we will work with you to meet your needs.

Learn more about our culture atclio.com/careers

We're a Human and High Performing AI company, meaning we use artificial intelligence to improve all of our operations. In recruitment, AI helps us streamline the process for greater efficiency. However, we've built our systems to ensure that a human always reviews AI-generated output, and we never make automated hiring decisions.

Disclaimer: We only communicate with candidates through official @clio.com email addresses.