Chief of Staff to CFO

Clover Health

1d•Remote

About The Position

Clover is seeking an exceptional Chief of Staff to serve as a strategic thought partner, execution leader, and force multiplier for the CFO. This highly consequential role is central to the company's financial and operating agenda, thriving at the intersection of strategy and execution. The Chief of Staff will extend the CFO's reach by driving critical cross-functional initiatives, translating ambiguity into action, and ensuring alignment on key decisions. The role requires moving fluidly between strategy and execution, quickly framing complex problems, and holding teams accountable for results. The ideal candidate possesses strong business judgment, structured thinking, analytical rigor, and low-ego leadership, designed for builders and systems thinkers with both strategic vision and operational instinct. Credibility with senior executives, effectiveness across functions, and a relentless focus on outcomes are essential.

Requirements

7–10+ years of experience in consulting, finance, strategy, business operations, investing, healthcare strategy, or other highly demanding operating environments.
A builder and systems thinker who breaks down ambiguous problems quickly, creates clarity proactively, and stays accountable for results.
Strong business judgment and excel at executive communication. Balance strategy and execution, write and speak with precision, and engage credibly with senior leaders.
Influence without authority and are analytically rigorous. Comfortable with data, financials, and business metrics to support recommendations.
High EQ and low ego: direct, thoughtful, adaptable, and willing to do whatever is needed to help the team win.
AI-fluent: deployed AI to accelerate execution and unlock leverage, and see opportunities others miss.
Bachelor's degree required

Nice To Haves

Healthcare experience is strongly preferred; experience in Medicare Advantage, value-based care, insurance, or related sectors is a significant plus.
MBA or advanced degree is a plus.

Responsibilities

Extend the CFO's Leverage: Shape priorities, operating rhythms, and decision-making across Finance and the broader company. Translate high-level goals into concrete execution plans with clear owners, timelines, and decision points. Act as a trusted thought partner by structuring problems, clarifying tradeoffs, and surfacing data-driven recommendations.
Lead High-Priority Initiatives: Independently drive the CFO's highest-priority initiatives that cut across finance, actuarial, operations, and product. Lead complex, ambiguous projects from definition through execution. Build action-oriented plans that focus teams on what matters most and translate strategy into measurable outcomes.
Strengthen Finance Operating Model: Partner with Finance, Actuarial, and Data teams to evolve finance into a more forward-looking, action-oriented function. Improve how key metrics are defined, tracked, and used to drive decisions. Ensure insights translate into decisions, behavior change, and accountability.
Drive Executive Communication: Prepare high-quality materials for Board, Audit Committee, investors, and executive leadership. Craft clear, analytically rigorous narratives around performance, strategic priorities, and risks. Review and refine presentations to ensure clarity and precision before they reach the CFO.
Improve Cross-Functional Alignment: Build relationships across finance, actuarial, operations, and product to drive collaboration. Identify misalignment early, force clarity, and resolve cross-functional issues before they become execution problems. Influence senior stakeholders without formal authority.
Elevate Decision Quality: Apply first-principles and data-driven thinking to help leadership solve difficult problems. Distill complex issues into decision-ready frameworks. Know when rigor matters most, when to go deep, and when speed trumps perfection.
Harness AI and Emerging Technology: Identify opportunities to deploy AI-powered tools that accelerate execution, improve decision quality, and unlock operational leverage. Build solutions, don't wait for permission.