Director, Strategic Initiatives - Legal AI

CoCounsel is central to Thomson Reuters' ambition to build a $1 billion legal AI business by July 2028. The Legal AI Business Accelerator brings product, commercial, marketing, customer, technology, data, finance, and operations teams together around a focused set of high-impact growth plays, with an operating model built on clear accountability, rapid decision-making, dedicated cross-functional teams, rigorous program management, and measurable outcomes.

We are seeking a Director, Strategic Initiatives to turn that ambition into execution. In this role, you will provide programmatic leadership for a critical accelerator pillar or strategic workstream—translating strategy into an integrated roadmap, establishing the operating cadence, resolving dependencies, and ensuring the team delivers measurable impact.

This is a high-visibility role for a strategic operator equally comfortable shaping an ambiguous problem, mobilizing a cross-functional team, and driving disciplined execution. Partnering closely with an accountable business leader and functional leaders, you'll serve as the connective tissue across the work—helping the team make choices, test hypotheses, remove barriers, and deliver outcomes, not simply track activity.

About the Role

As Director of Strategic Initiatives, you will:

• 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 the talent, funding, data, tools, and functional capacity required to deliver
• Define success measures and establish a fact-based performance rhythm—tracking leading indicators, customer outcomes, commercial impact, and delivery progress, and recommending where to double down, pivot, or stop
• 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—so customers experience a coherent journey rather than disconnected functional handoffs
• Develop executive-ready communications, SteerCo materials, business cases, and decision briefs that make tradeoffs and required actions clear
• Partner on change management and capability building so new operating models, processes, and behaviors are adopted and sustained
• Capture reusable playbooks and lessons that 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 because tradeoffs, data, and escalation paths are explicit
• 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 translates rapidly into changes in product, go-to-market motions, and execution priorities
• The program develops durable playbooks and operating mechanisms reusable across accelerator priorities

About You

You're a fit for the Director of Strategic Initiatives role if your background includes:

• 7+ years in business transformation, strategic program leadership, strategy execution, product or go-to-market operations, or comparable experience in a complex enterprise environment
• A 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
• A 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