Director Strategic Initiatives Jobs in Wisconsin

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.

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

• 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

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

• 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

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• Flexibility & Work‑Life Balance: Flex My Way is a set of supportive workplace policies designed to help manage personal and professional responsibilities, whether caring for family, giving back to the community, or finding time to refresh and reset. This builds upon our flexible work arrangements, including work from anywhere for up to 8 weeks per year, empowering employees to achieve a better work‑life balance.
• Career Development and Growth: By fostering a culture of continuous learning and skill development, we prepare our talent to tackle tomorrow’s challenges and deliver real‑world solutions. Our Grow My Way programming and skills‑first approach ensures you have the tools and knowledge to grow, lead, and thrive in an AI‑enabled future.
• Industry Competitive Benefits: We offer comprehensive benefit plans to include flexible vacation, two company‑wide Mental Health Days off, access to the Headspace app, retirement savings, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing.
• Culture: Globally recognized, award‑winning reputation for inclusion and belonging, flexibility, work‑life balance, and more. We live by our values: Obsess over our Customers, Compete to Win, Challenge (Y)our Thinking, Act Fast / Learn Fast, and Stronger Together.
• Social Impact: Make an impact in your community with our Social Impact Institute. We offer employees two paid volunteer days off annually and opportunities to get involved with pro‑bono consulting projects and Environmental, Social, and Governance (ESG) initiatives.
• Making a Real‑World Impact:We are one of the few companies globally that helps its customers pursue justice, truth, and transparency. Together, with the professionals and institutions we serve, we help uphold the rule of law, turn the wheels of commerce, catch bad actors, report the facts, and provide trusted, unbiased information to people all over the world.

In the United States, Thomson Reuters offers a comprehensive benefits package to our employees. Our benefit package includes market competitive health, dental, vision, disability, and life insurance programs, as well as a competitive 401k plan with company match. In addition, Thomson Reuters offers market leading work life benefits with competitive vacation, sick and safe paid time off, paid holidays (including two company mental health days off), parental leave, sabbatical leave. These benefits meet or exceeds the requirements of paid time off in accordance with any applicable state or municipal laws.

• optional hospital, accident and sickness insurance paid 100% by the employee;
• optional life and AD&D insurance paid 100% by the employee;
• Flexible Spending and Health Savings Accounts;
• fitness reimbursement;
• access to Employee Assistance Program;
• Group Legal Identity Theft Protection benefit paid 100% by employee;
• access to 529 Plan;
• commuter benefits;
• Adoption & Surrogacy Assistance;
• Tuition Reimbursement;
• and access to Employee Stock Purchase Plan.

Thomson Reuters complies with local laws that require upfront disclosure of the expected pay range for a position. The base compensation range varies across locations.For any eligible US locations, unless otherwise noted, the base compensation range for this role is $137,200 USD - $254,800 USD.Base pay is positioned within the range based on several factors including an individual’s knowledge, skills and experience with consideration given to internal equity. Base pay is one part of a comprehensive Total Reward program which also includes flexible and supportive benefits and other wellbeing programs.This role may also be eligible for an Annual Bonus based on a combination of enterprise and individual performance.This job posting will close 09/17/2026.

Thomson Reuters informs the way forward by bringing together the trusted content and technology that people and organizations need to make the right decisions. We serve professionals across legal, tax, accounting, compliance, government, and media. Our products combine highly specialized software and insights to empower professionals with the data, intelligence, and solutions needed to make informed decisions, and to help institutions in their pursuit of justice, truth, and transparency. Reuters, part of Thomson Reuters, is a world leading provider of trusted journalism and news.

We are powered by the talents of 26,000 employees across more than 70 countries, where everyone has a chance to contribute and grow professionally in flexible work environments. At a time when objectivity, accuracy, fairness, and transparency are under attack, we consider it our duty to pursue them. Sound exciting? Join us and help shape the industries that move society forward.

As a global business, we rely on the unique backgrounds, perspectives, and experiences of all employees to deliver on our business goals. To ensure we can do that, we seek talented, qualified employees in all our operations around the world regardless of race, color, sex/gender, including pregnancy, gender identity and expression, national origin, religion, sexual orientation, disability, age, marital status, citizen status, veteran status, or any other protected classification under applicable law. Thomson Reuters is proud to be an Equal Employment Opportunity Employer providing a drug‑free workplace.

We also make reasonable accommodations for qualified individuals with disabilities and for sincerely held religious beliefs in accordance with applicable law. More information on requesting an accommodation here.

More information about Thomson Reuters can be found on thomsonreuters.com