Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Dropbox is seeking a highly organized and strategic Legal Operations Associate to join our Legal team. This individual will play a critical role in supporting the operational infrastructure that underpins our legal function. You will manage and optimize multiple legal systems, partner cross-functionally with internal teams, and serve as a key driver of efficiency and innovation across the legal organization.

Design and lead legal team workflows, policies, and processes to improve efficiency.

Implement and manage legal technology tools (e.g., CLM, eBilling, matter management).

Drive legal department KPIs, reporting, and dashboards to measure performance and value.

Support the rollout of Legal’s front door in Jira Service Management and the onboarding of additional Legal teams, including testing changes, documenting configurations, and training users.

Oversee outside counsel and legal vendor engagements, onboarding, and billing.

Manage the legal team’s tech stack and collaborate with IT as needed.

Ensure smooth communication between Legal and business stakeholders.

Partner with Legal teams to translate process needs into practical configurations and refine workflows based on user feedback and request trends.

Coordinate with CIT and the Atlassian team for platform guidance, troubleshooting, integrations, and changes requiring broader technical support.

Maintain centralized repositories for contracts, templates, policies, and legal knowledge.

Help maintain Legal’s Confluence knowledge base, working with subject‑matter owners to organize approved guidance and support self‑service and AI‑assisted responses.

Lead or support legal projects from planning to execution, including process improvement and change adoption.

3+ years of experience in legal operations, strong track record for project management, or operations roles within a legal department or law firm.

Tech industry experience and familiarity with commercial transactions strongly preferred.

Background experience with legal systems and technologies such as JSM, Confluence,



Ironclad, Spellbook, and Brightflag knowledge are a plus, but not required.

Strong track record for project management and process optimization.

Familiarity with contracting and procurement processes, as well as with negotiating, drafting and advising clients on commercial contracts is a plus but not required.

Familiarity with knowledge management, content organization and access controls.

Ability to translate business requirements into system configurations, troubleshoot issues and document changes.

BA/BS from a top university and excellent academic credentials.

Strong preference for this candidate to have previously worked in tech and virtual first — to understand the fast paced style of collaborating quickly, being agile, embracing change, and knowing how to obtain urgent approvals and input.

Hands‑on JSM administration experience, including configuring and testing forms, fields, queues, workflows, routing or automation, and reporting.

Familiarity with team‑managed JSM projects and working within shared platform standards.

AI fluency means using these tools to amplify human judgment, not replace it. We believe people with these skills will thrive as work and technology continue to evolve:

To learn more about why these skills matter and what the data shows about thriving through change, read this blog post from our Chief People Officer, Melanie Rosenwasser.

102,000—$138,000 CAD

All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).

We’re a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work.



Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships. With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically, stay curious, and use up-to-date tools, including AI, to improve how work gets done. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. The Dropbox Legal, Policy, Trust & Privacy Team safeguards our company to enable innovation while protecting our users, platform, and business. From governance, risk & compliance to public policy, we combine creative problem‑solving with subject‑matter expertise expertise to help our employees and users work securely, drive responsible growth, and shape the future of policy around technology. If you're excited about protecting trust in the digital age, join our Legal team.

Virtual First

Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. While remote work is the primary experience for our employees, we also prioritize intentional, in‑person connection. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.

This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). It’s not about being an expert—it’s about using these tools thoughtfully and effectively to improve your work and support others.

Ownership: You use AI responsibly by protecting data, applying sound judgment, and taking accountability for the quality and accuracy of your work.

Together, these behaviors help build a workforce where technology amplifies human judgment, creativity, and impact.

We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work.

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📌 Legal Operations Specialist (Remote) (Ottawa)
🏢 Dropbox
📍 Ottawa