Chief of Staff (Legal)

About the Role

OpenLoop is looking for a Chief of Staff to the General Counsel. We power telehealth for brands across all 50 states, in one of the most regulated and fastest-moving parts of healthcare. As the GC's strategic partner and a member of the legal leadership team, you'll help shape the department's strategy, drive its most important initiatives and ensure executive decisions translate into measurable results.

You'll work across Legal, Compliance and the broader business to navigate complex priorities, drive strategic initiatives and strengthen how the organization operates as it scales. You'll also own the department's operating model, including legal operations, AI adoption, budgets and how Legal works with the rest of the business, acting as a trusted advisor and representative of the GC.

What You'll Do

• Shape the department's strategy and annual priorities with the GC, translating business objectives into actionable plans and making critical trade-offs across competing priorities, resources and investments.
• Drive the execution of the GC's most important strategic initiatives, bringing together Legal, Compliance and business leadership to solve complex problems and deliver measurable outcomes.
• Partner with VP and SVP leaders across the company, influencing decisions, navigating competing interests and driving alignment on initiatives that extend beyond the Legal function.
• Lead Legal's involvement in major corporate transactions, including acquisitions, fundraising and strategic partnerships, coordinating diligence, data rooms and cross-functional execution alongside the corporate legal team.
• Act as a strategic advisor and extension of the GC, representing them in selected leadership discussions, anticipating emerging challenges and ensuring decisions translate into action.
• Own leadership meetings, offsites and planning cycles, establishing a consistent operating rhythm and holding leaders accountable for commitments and results.
• Own leadership communications for the department, synthesizing complex business and legal issues into clear recommendations, executive updates and materials for Board discussions.
• Lead strategic transformation across Legal, identifying opportunities to improve organizational effectiveness, cross-functional collaboration and how the function supports the company's growth.
• Own the legal budget, outside counsel spend and departmental performance reporting, establishing clear financial accountability and visibility into the function's effectiveness.
• Set the direction for Legal's use of AI, automation, contract management and intake tools, partnering with IT on delivery and building the legal operations capability and team as the department scales.

Who You Are

• 10+ years of experience, including several years as a Chief of Staff, strategy lead or senior operator working directly with senior executives, with demonstrated ownership of complex strategic initiatives and their execution.
• Experience leading or playing a significant role in major corporate transactions, including fundraising, acquisitions or other complex strategic processes, with exposure to due diligence, data rooms and stakeholder coordination.
• A record of leading cross-functional transformation, including AI and automation adoption that delivered measurable improvements in how an organization operates.
• Experience in large-scale or rapidly scaling organizations, with the ability to anticipate where structures, processes and systems need to evolve.
• A strong working knowledge of legal operations, including CLM, intake and legal technology, sufficient to set direction and lead specialists.
• Experience owning departmental budgets, resource planning or outside counsel spend.
• Experience leading teams and developing people, with a track record of building capability, accountability and strong performance.
• The executive judgment, credibility and presence to influence VP and SVP leaders without direct authority and represent the GC in high-stakes discussions.
• Strong strategic and commercial judgment, with the ability to connect business priorities, legal considerations and operational realities while moving comfortably between strategy and execution.

Preferred Qualifications

• Healthcare or regulated industry experience.
• Experience with Ironclad.
• A background spanning consulting, strategy or operations as well as legal.
• Experience working directly with a General Counsel, Chief Legal Officer or executive leadership team.

Our Benefits

In addition, for salaried positions you would also be eligible for

• Medical, Dental, and Vision plans
• Flexible Spending/Health Savings Accounts
• Flexible PTO
• 401(k) + Company Match
• Life Insurance, Pet insurance, and more