Senior Director, Innovation and Delivery

cloverhealth; United States; Remote; USD 200,000 - 250,000; Full time

Job summary

Clover Health seeks a strategic leader to own high-priority initiatives, navigating between strategy and hands-on leadership. You will turn ambiguous priorities into measurable outcomes and prepare them for long-term ownership.

Applicants should bring a track record of operating in high-judgment environments, the ability to diagnose complex problems, and credibility with senior executives across functions. The role emphasizes durable systems and a remote-first working model.

Qualifications

• Extensive experience in high-judgment environments (investing, consulting, strategy, operations, or startup leadership).
• Ability to diagnose complex problems and move between strategic framing and details.
• Track record of delivering high-stakes, ambiguous work to concrete outcomes.
• Ability to design durable systems aligning decisions, incentives, and teams.
• Credibility with senior executives across functions.
• Comfort with an evolving remit and incomplete information.

Responsibilities

• Take interim ownership of strategic initiatives with fragmented or emerging leadership.
• Diagnose operating challenges, clarify priorities, and align senior leaders across functions.
• Design practical operating models, accountability structures, and decision rhythms.
• Identify and apply AI or emerging technology to improve healthcare operations and outcomes.
• Drive initiatives through measurable results and resolve obstacles as scope evolves.
• Transition successful work to a permanent leader, team, or organizational structure.

Skills

Strategic leadership

Cross-functional collaboration

Problem diagnosis

Decision making under uncertainty

Executive influence

Job description

Role overview

Lead high-priority initiatives that need clearer ownership, stronger execution, or a new operating model. You'll move between strategy and hands-on business leadership, using sound judgment to turn ambiguous priorities into measurable outcomes and leave them ready for long-term ownership.

Responsibilities

• Take interim business ownership of a strategic initiative or domain with fragmented or emerging leadership.
• Diagnose operating challenges, clarify priorities and decisions, and align senior leaders across functions.
• Design practical operating models, accountability structures, and decision rhythms that help work continue reliably.
• Identify and apply AI or other emerging technology to improve healthcare operations and outcomes.
• Drive initiatives through measurable results, resolving obstacles as scope and ownership evolve.
• Transition successful work to a permanent leader, team, or organizational structure.

Requirements

• Extensive experience in a high-judgment operating environment, such as investing, consulting, strategy, business operations, or startup leadership; the source cites 10+ years as an example.
• Ability to quickly diagnose complex business problems and move between strategic framing and operational detail.
• A record of delivering high-stakes, ambiguous work through to concrete outcomes.
• Strength in building durable systems and improving how decisions, incentives, and teams fit together.
• Credibility with senior executives and the ability to work across organizational levels.
• Comfort with an intense, evolving remit and incomplete information.

Benefits and work setup

• Remote-first work, flexible time off, monthly company holidays, and No-Meeting Fridays.
• Health and mental well-being resources, paid parental leave, and professional development support.
• Employee stock purchase plan, office setup reimbursement, and monthly phone and internet stipend.
• Published base salary range: $200,000-$250,000 USD.