Director, Strategic Initiatives - Legal AI

About the Role

As Director of Strategic Initiatives, you will lead the strategy-to-execution process for an assigned accelerator pillar within Thomson Reuters' Legal AI Business Accelerator. This high-visibility role involves translating enterprise growth objectives into clear charters, roadmaps, and measurable outcomes while serving as the connective tissue across cross-functional teams.

• Lead the strategy-to-execution process for an assigned accelerator pillar, converting enterprise growth objectives into a clear charter, roadmap, milestones, and decision points
• Build and run the program operating system, including governance, leadership forums, working-team cadence, decision rights, dependency management, and risk escalation
• Mobilize dedicated cross-functional teams across Product, Engineering, Sales, Marketing, Customer Success, Operations & Technology, Data & Analytics, Finance, Legal, and other shared services
• Facilitate discovery sessions and workshops that surface customer and business pain points, align stakeholders, and turn competing perspectives into executable decisions
• Maintain an integrated view of scope, resources, sequencing, and interdependencies; identify capability gaps and work with leaders to secure talent, funding, data, tools, and functional capacity
• Define success measures and establish a fact-based performance rhythm—tracking leading indicators, customer outcomes, commercial impact, and delivery progress, and recommending adjustments
• Champion rapid experimentation and test-and-learn ways of working while maintaining accountability for commitments, quality, and pace
• Connect work across the full customer lifecycle—from awareness and trial through onboarding, adoption, renewal, expansion, and advocacy—for a coherent customer journey
• Develop executive-ready communications, SteerCo materials, business cases, and decision briefs that clarify tradeoffs and required actions
• Partner on change management and capability building to adopt and sustain new operating models, processes, and behaviors
• Capture reusable playbooks and lessons to strengthen execution across the accelerator

What Success Looks Like

• Within 90 days, the assigned pillar has a clear charter, accountable owners, validated outcomes, an integrated roadmap, a functioning governance cadence, and transparent risks and dependencies
• Cross-functional leaders make faster, better-informed decisions due to explicit tradeoffs, data, and escalation paths
• Teams deliver against milestones with measurable progress on pillar-relevant outcomes (e.g., trial conversion, onboarding speed, adoption, value realization, renewal, expansion, or revenue)
• Customer and market learning rapidly translates into changes in product, go-to-market motions, and execution priorities
• The program develops durable playbooks and operating mechanisms reusable across accelerator priorities

Requirements

• 7+ years in business transformation, strategic program leadership, strategy execution, product or go-to-market operations, or comparable experience in a complex enterprise environment
• Track record of leading complex, cross-functional initiatives that delivered measurable commercial, customer, product, or operational impact
• Ability to move fluidly between strategy and execution—framing problems, building plans, establishing operating discipline, and driving work through ambiguity and change
• Exceptional facilitation, influence, and stakeholder-management skills, with the judgment to challenge constructively and align senior leaders and delivery teams without relying on direct authority
• Strong analytical and business-case capabilities, including defining metrics, evaluating performance, and using evidence to recommend action
• Executive presence and outstanding written/verbal communication skills, with the ability to simplify complex issues into crisp, decision-oriented materials
• Experience applying agile, lean, product operating model, OKR, or similar approaches to improve focus, speed, and value delivery
• Persistence, adaptability, and sound judgment in a fast-moving, matrixed environment with incomplete information
• Customer-first mindset and genuine interest in how AI is reshaping professional work and business models

Preferred Qualifications

• Legal technology, AI-enabled products, SaaS, professional information services, or another B2B enterprise technology environment
• Familiarity with product-led growth, enterprise go-to-market transformation, customer lifecycle optimization, adoption/value realization, renewals and expansion, or ecosystem partnerships
• Working knowledge of enterprise platforms and tools such as Salesforce, Gainsight, Gong, Miro, or Microsoft Planner/Teams
• Experience leading programs spanning multiple customer segments, geographies, or functions
• MBA or other relevant advanced degree

Benefits

• Flexibility & Work-Life Balance: Flex My Way policies, including work from anywhere for up to 8 weeks per year, flexible work arrangements, and supportive workplace policies for personal and professional responsibilities
• Career Development and Growth: Culture of continuous learning with Grow My Way programming, skills-first approach, and tools for professional growth in an AI-enabled future
• Industry Competitive Benefits: Comprehensive benefit plans including flexible vacation, two company-wide Mental Health Days off, access to the Headspace app, retirement savings with company match, tuition reimbursement, and employee incentive programs
• Wellbeing Resources: Support for mental, physical, and financial wellbeing, including optional hospital, accident, and sickness insurance; fitness reimbursement; Employee Assistance Program; and Group Legal Identity Theft Protection
• Additional Benefits: Paid holidays, parental leave, sabbatical leave, adoption & surrogacy assistance, commuter benefits, 529 Plan access, and Employee Stock Purchase Plan
• Culture: Globally recognized for inclusion and belonging, flexibility, and work-life balance, guided by values: Obsess over our Customers, Compete to Win, Challenge (Y)our Thinking, Act Fast / Learn Fast, and Stronger Together
• Social Impact: Two paid volunteer days off annually, opportunities for pro-bono consulting projects, and involvement in Environmental, Social, and Governance (ESG) initiatives through the Social Impact Institute
• Making a Real-World Impact: Contribute to upholding the rule of law, turning the wheels of commerce, catching bad actors, reporting facts, and providing trusted, unbiased information globally

Pay

The base compensation range for this role is $137,200 USD - $254,800 USD, positioned within the range based on knowledge, skills, experience, and internal equity. This role may also be eligible for an Annual Bonus based on a combination of enterprise and individual performance.