Director, Strategic Initiatives – Legal AI

This is a fully remote position, open to applicants in California, +4 more states.

📋 Description

• Lead the strategy-to-execution process for a designated Legal AI accelerator pillar.

• Translate enterprise growth objectives into charters, roadmaps, milestones, and decision-making points.

• Establish and manage program governance, leadership forums, team cadence, decision rights, dependency management, and risk escalation.

• Mobilize cross-functional teams across various departments including Product, Engineering, Sales, Marketing, Customer Success, Operations, Technology, Data & Analytics, Finance, Legal, and shared services.

• Conduct discovery sessions and workshops to identify customer and business pain points, facilitating actionable decisions.

• Maintain comprehensive views of scope, resources, sequencing, and interdependencies.

• Recognize capability gaps and procure talent, funding, data, tools, and functional capacity.

• Establish success metrics and monitor leading indicators, customer outcomes, commercial impact, and progress on delivery.

• Advise on whether to intensify efforts, pivot, or cease initiatives based on performance data.

• Advocate for rapid experimentation and a test-and-learn approach to work.

• Connect initiatives throughout the customer lifecycle from awareness and trial to onboarding, adoption, renewal, expansion, and advocacy.

• Create communications suitable for executives, SteerCo materials, business cases, and decision briefs.

• Collaborate on change management and capability enhancement.

• Document reusable playbooks and insights for future accelerator initiatives.

⛳️ Requirements

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

• Proven history of leading intricate cross-functional initiatives with measurable impacts on commercial, customer, product, or operational outcomes.

• Capability to transition between strategy and execution, define problems, create plans, implement operating discipline, and navigate work through ambiguity and change.

• Outstanding facilitation, influence, and stakeholder management abilities.

• Strong analytical and business case skills, including setting metrics, assessing performance, and making recommendations based on evidence.

• Executive presence along with excellent written and verbal communication skills.

• Experience with agile, lean, product operating models, OKR, or similar methodologies.

• Demonstrated persistence, adaptability, and sound judgment in a dynamic, matrixed environment.

• Customer-centered mindset and interest in the impact of AI on professional work and business models.

• Preferred experience in legal technology, AI-driven products, SaaS, professional information services, or B2B enterprise technology.

• 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 Salesforce, Gainsight, Gong, Miro, or Microsoft Planner/Teams.

• Experience managing programs across multiple customer segments, geographies, or functions.

• An MBA or another relevant advanced degree is preferred.

🏝️ Benefits

• Flexible work arrangements, including the ability to work from anywhere for up to 8 weeks each year.

• Flexible vacation policy.

• Two company-wide Mental Health Days off.

• Access to the Headspace app.

• Retirement savings options.

• Tuition reimbursement program.

• Employee incentive programs.

• Resources for mental, physical, and financial wellbeing.

• Two paid volunteer days off each year.

• Opportunities for pro-bono consulting projects.

• Participation in Environmental, Social, and Governance (ESG) initiatives.

• Health, dental, vision, disability, and life insurance programs.

• Competitive 401(k) plan with company matching.

• Paid sick and safe time off.

• Paid holidays, including two company mental health days off.

• Parental leave benefits.

• Sabbatical leave options.

• Optional hospital, accident, and sickness insurance.

• Optional life and AD&D insurance.

• Flexible Spending Accounts available.

• Health Savings Accounts options.

• Fitness reimbursement benefits.

• Employee Assistance Program support.

• Group Legal Identity Theft Protection benefit.

• 529 Plan available.

• Commuter benefits offered.

• Adoption & Surrogacy Assistance provided.

• Employee Stock Purchase Plan opportunities.

• Annual Bonus based on enterprise and individual performance.