Director, Strategic Initiatives - Legal AI

About the Role

As Director of Strategic Initiatives, 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 ambiguous problems, mobilizing cross-functional teams, and driving disciplined execution.

• 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

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
• 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

Benefits

• Flexibility & Work-Life Balance: Flex My Way policies support managing personal and professional responsibilities, 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 a skills-first approach provide tools and knowledge for continuous learning and professional growth in an AI-enabled future.
• 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., access to the Headspace app).
• Culture: Globally recognized for inclusion and belonging, flexibility, and work-life balance, guided by values such as obsessing over customers, competing to win, and acting fast/learning fast.
• Social Impact: Opportunities to make an impact through the Social Impact Institute, including two paid volunteer days off annually, pro-bono consulting projects, and Environmental, Social, and Governance (ESG) initiatives.
• Making a Real-World Impact: Contribute to upholding the rule of law, turning the wheels of commerce, and providing trusted, unbiased information globally.
• Additional benefits include market-competitive health, dental, vision, disability, and life insurance; optional hospital, accident, sickness, life, and AD&D insurance; Flexible Spending and Health Savings Accounts; fitness reimbursement; Employee Assistance Program; Group Legal Identity Theft Protection; 529 Plan; commuter benefits; Adoption & Surrogacy Assistance; Tuition Reimbursement; and 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 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.