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 mobilizing cross-functional teams across Product, Engineering, Sales, Marketing, Customer Success, Operations & Technology, Data & Analytics, Finance, Legal, and other shared services.

• Build and run the program operating system, including governance, leadership forums, working-team cadence, decision rights, dependency management, and risk escalation.
• Facilitate discovery sessions and workshops to 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 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.
• 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 to ensure a coherent journey rather than disconnected functional handoffs.
• 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 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 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 Experience

• 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 two company-wide Mental Health Days off.
• Career Development and Growth: Grow My Way programming and skills-first approach to continuous learning and skill development.
• Industry Competitive Benefits: Comprehensive benefit plans including flexible vacation, retirement savings with company match, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing (e.g., Headspace app).
• Culture: Globally recognized for inclusion and belonging, flexibility, and work-life balance, guided by values such as customer obsession, competitiveness, and collaboration.
• Social Impact: Two paid volunteer days off annually, opportunities for pro-bono consulting projects, and Environmental, Social, and Governance (ESG) initiatives through the Social Impact Institute.
• Additional Benefits:
  • Market-competitive health, dental, vision, disability, and life insurance programs.
  • 401k plan with company match.
  • Paid holidays, parental leave, and sabbatical leave.
  • Optional hospital, accident, sickness, life, and AD&D insurance.
  • Flexible Spending and Health Savings Accounts.
  • Fitness reimbursement and Employee Assistance Program.
  • Group Legal Identity Theft Protection benefit.
  • Access to 529 Plan, commuter benefits, Adoption & Surrogacy Assistance, and Tuition Reimbursement.
  • Employee Stock Purchase Plan.

Pay

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