Director Strategy and Operations AI

Skills

About the Role

You will lead AI transformation by building knowledge-management infrastructure, improving AI-enabled workflows, and identifying high-impact opportunities across the business. You will partner with senior leaders to define strategic initiatives, translate goals into measurable plans, and lead cross-functional execution. You will also support planning, resource allocation, organizational design, and scalable operating practices.

Requirements

• 4–7 years of experience in strategy, operations, consulting, product operations, or a high-growth technology environment
• Strong interest in AI and its impact on work
• Strong business judgment across systems, incentives, and organizational behavior
• Ability to lead complex initiatives across teams without direct management authority
• Analytical ability with data, models, metrics, and dashboards
• Exceptional written communication
• Knowledge-management, internal operations, or AI-tooling experience is preferred
• Healthcare, benefits, or complex B2B-business experience is preferred
• Active work authorization in the United States

Responsibilities

• Build and maintain knowledge-management infrastructure, including documentation, decision logs, and organizational context for AI agents
• Lead adoption of AI-enabled practices across teams
• Partner with Product and Engineering leadership to design data, systems, and workflows for real-time decision-making
• Identify and implement high-leverage AI opportunities across clinical operations, sales, product, and member experience
• Advise leadership on culture and organizational design in the age of AI
• Partner with executives to define and drive strategic initiatives
• Translate company goals into cross-functional plans, milestones, and measurable outcomes
• Support leadership decision-making with analysis, judgment, and recommendations
• Lead high-priority cross-functional initiatives
• Clarify ownership, remove bottlenecks, and maintain momentum across functions
• Build operating rhythms, reviews, and forums that keep teams aligned
• Partner on annual planning, resource allocation, and organizational design
• Continuously improve operating practices as the organization grows

Benefits

• Equity
• Employer-covered health, dental, and insurance plan options
• Access to the full platform and specialists for mental health, reproductive health, family planning, and pediatrics
• Wellness partnerships
• Hybrid work
• In-office meals
• Work Together Days
• 16 weeks of fully paid parental leave
• New parent stipend for eligible employees
• 401K matching with immediate vesting