Senior Director, Innovation & Delivery

Clover is entering a period of meaningful build. As the company pushes forward on a set of important strategic priorities, we need leaders who can help translate vision into operating reality. Some of this work will involve standing up new capabilities. Some will involve shaping and accelerating critical initiatives that cut across functions. All of it will require leaders who can bring structure, judgment, and momentum to areas that matter disproportionately to Clover’s future.

We’re hiring a senior operator into Innovation & Delivery to help bring the CEO’s vision to life in some of the company’s most important areas of development. This is a high-leverage operating role 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.

This role is designed for builders and systems thinkers: people who are energized by creating clarity, shaping how work gets done, and helping a company develop new muscles at moments that matter.

As a Senior Director, Innovation & Delivery, you will:

• 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 looks like:

• 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.

You should get in touch if:

• You’ve built your career in elite, high-judgment environments — for example 10+ years in investing, consulting, business operations, strategy, startup leadership, or other highly selective operator tracks.
• You have the pattern recognition to quickly diagnose messy business problems and the range to move from strategy to operating detail without losing altitude.
• You are not looking to run an IT transformation office, manage a PMO, or operate as a process administrator.
• You are 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.
• You are a systems thinker: you naturally see how incentives, decisions, interfaces, and organizational design interact — and you know how to reshape them.
• You’ve taken on ambiguous, high-stakes work with incomplete information and still driven it to a real outcome.
• You are credible with senior executives and can work effectively with leaders across the company, including the CEO, Chairman, and OpCo.
• You are comfortable stepping into roles that are intense, temporary, and highly leveraged — where the expectation is to build, stabilize, and transition, not simply to advise.
• You care more about solving consequential business problems than about protecting a narrow functional lane.

Benefits Overview

• Financial Well-Being: Our commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, we offer a performance-based bonus program, 401k matching, and regular compensation reviews to recognize and reward exceptional contributions.
• Physical Well-Being: We prioritize the health and well-being of our employees and their families by providing comprehensive medical, dental, and vision coverage. Your health matters to us, and we invest in ensuring you have access to quality healthcare.
• Mental Well-Being: We understand the importance of mental health in fostering productivity and maintaining work-life balance. To support this, we offer initiatives such as No-Meeting Fridays, monthly company holidays, access to mental health resources, and a generous flexible time-off policy. Additionally, we embrace a remote-first culture that supports collaboration and flexibility, allowing our team members to thrive from any location.
• Professional Development: Developing internal talent is a priority for Clover. We offer 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
• And much more!

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.

From Clover’s inception, Diversity & Inclusion have always been key to our success. We are an Equal Opportunity Employer and our employees are people with different strengths, experiences, perspectives, opinions, and backgrounds, who share a passion for improving people's lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All of our employee’s points of view are key to our success, and inclusion is everyone’s responsibility.