Senior Director, Innovation and Delivery

About the role

Clover is entering a period of meaningful build. As the company pushes forward on important strategic priorities, we need leaders who can help translate vision into operating reality. This high-leverage operating role is for someone who can step into emerging priorities, build the right operating model, align leaders around clear decisions, and help turn new ideas into durable parts of the business. Designed for builders and systems thinkers, this role is energized by creating clarity, shaping how work gets done, and helping a company develop new muscles at moments that matter.

Responsibilities

• Step into Critical Ownership Gaps: Serve as the interim business-side leader for a major initiative or strategic domain where ownership is missing, fragmented, or still emerging.
• Build the Operating Model: Create the structure, decision cadence, working model, and accountability mechanisms required to make the work durable.
• Harness AI & Emerging Technology: Identify, architect, and deploy AI-powered tools and approaches to accelerate execution and unlock solutions to some of the hardest, most intractable problems in healthcare—from care gap closure to operational efficiency to member outcomes.
• Drive Business Outcomes, Not Just Activity: Own the work through measurable progress and concrete results—not just coordination, reporting, or process management.
• Stabilize and Scale Underbuilt Areas: Bring order, momentum, and clarity to important domains that need to be built, stabilized, or materially reshaped.
• Lead Through Ambiguity: When the path is unclear, define it. When ownership is diffuse, consolidate it. When a function or initiative is stuck, unblock it.
• Prepare the Long-Term Handoff: Help transition the work to a durable long-term owner, team, or org structure once the model is working.

Success in this role

• First 90 days: Build a sharp understanding of Clover’s business model, operating context, and leadership dynamics; take ownership of a critical initiative or domain; clarify scope, decisions, and near-term priorities.
• First 6 months: Create visible traction in a high-priority area by stabilizing execution, improving decision quality, and building the core operating model needed to move the work forward.
• First year: Deliver meaningful business outcomes, establish a stronger and more durable ownership model, and leave behind a function, initiative, or system that is materially stronger than you found it.

Qualifications

• Built your career in elite, high-judgment environments—e.g., 10+ years in investing, consulting, business operations, strategy, startup leadership, or other highly selective operator tracks.
• Pattern recognition to quickly diagnose messy business problems and the range to move from strategy to operating detail without losing altitude.
• Not looking to run an IT transformation office, manage a PMO, or operate as a process administrator.
• A builder: you like creating structure where none exists, designing operating systems that hold up in the real world, and turning ambiguity into durable execution.
• A systems thinker: you naturally see how incentives, decisions, interfaces, and organizational design interact—and you know how to reshape them.
• Taken on ambiguous, high-stakes work with incomplete information and still driven it to a real outcome.
• Credible with senior executives and can work effectively with leaders across the company, including the CEO, Chairman, and OpCo.
• Comfortable stepping into roles that are intense, temporary, and highly leveraged—where the expectation is to build, stabilize, and transition, not simply to advise.
• Care more about solving consequential business problems than about protecting a narrow functional lane.

Benefits

• Financial Well-Being: Competitive base salary and equity opportunities, performance-based bonus program, 401k matching, and regular compensation reviews.
• Physical Well-Being: Comprehensive medical, dental, and vision coverage.
• Mental Well-Being: No-Meeting Fridays, monthly company holidays, access to mental health resources, generous flexible time-off policy, and a remote-first culture.
• Professional Development: Learning programs, mentorship, professional development funding, and regular performance feedback and reviews.
• Additional Perks:
  • Employee Stock Purchase Plan (ESPP) offering discounted equity opportunities
  • Reimbursement for office setup expenses
  • Monthly cell phone & internet stipend
  • Remote-first culture enabling collaboration with global teams
  • Paid parental leave for all new parents

Pay

A reasonable estimate of the base salary range for this role is $204,000—$240,000 USD.

About Clover

We are reinventing health insurance by combining the power of data with human empathy to keep our members healthier. We believe the healthcare system is broken, so we've created custom software and analytics to empower our clinical staff to intervene and provide personalized care to the people who need it most. We always put our members first, and our success as a team is measured by the quality of life of the people we serve. Those who work at Clover are passionate and mission-driven individuals with diverse areas of expertise, working together to solve the most complicated problem in the world: healthcare.