Clover is looking for an exceptional Chief of Staff to partner closely with the CFO as a strategic thought partner, execution leader, and force multiplier across the organization. This is a highly consequential role at the center of the company's financial and operating agenda.

This is a high-leverage operating role for someone who thrives at the intersection of strategy and execution. You'll extend the CFO's reach by driving critical cross-functional initiatives, translating ambiguity into action, and ensuring leaders are aligned on the decisions and actions that matter most. You'll move fluidly between strategy and execution, frame complex problems quickly, and hold teams accountable for results.

The ideal candidate combines strong business judgment, structured thinking, and analytical rigor with low-ego leadership. This role is designed for builders and systems thinkers who bring both strategic vision and operational instinct. You're credible with senior executives, effective across functions, and relentlessly focused on outcomes over activity.

As a Chief of Staff to the CFO, you will:

• 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.

Success in this role looks like:

• First 90 days: Build trust with the CFO and key cross-functional leaders. Establish a clear operating framework for tracking and advancing priorities. Drive critical initiatives with visible traction and accountability.
• First 6 months: Independently lead multiple high-priority initiatives with measurable progress. Build strong relationships across leadership and be viewed as a trusted, high-judgment partner. Improve quality of executive materials and cross-functional execution.
• First year: Play a meaningful role in shaping and executing the company's strategic and financial agenda. Help finance become a more effective driver of business performance. Serve as a critical multiplier for the CFO and trusted leader at the center of the business.

You should get in touch if:

• You have 7–10+ years of experience in consulting, finance, strategy, business operations, investing, healthcare strategy, or other highly demanding operating environments.
• You're a builder and systems thinker who breaks down ambiguous problems quickly, creates clarity proactively, and stays accountable for results.
• You have strong business judgment and excel at executive communication. You balance strategy and execution, write and speak with precision, and engage credibly with senior leaders.
• You influence without authority and are analytically rigorous. You're comfortable with data, financials, and business metrics to support recommendations.
• You have high EQ and low ego: you're direct, thoughtful, adaptable, and willing to do whatever is needed to help the team win.
• You're AI-fluent: you've deployed AI to accelerate execution and unlock leverage, and you see opportunities others miss.
• Healthcare experience is strongly preferred; experience in Medicare Advantage, value-based care, insurance, or related sectors is a significant plus. Bachelor's degree required; MBA or advanced degree is a plus.

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.

#LI-REMOTE

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.

At Clover Health, 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 are seeking a strategic, operationally-focused Director, Strategic Finance (Medicare Advantage) to serve as the primary financial architect for our core insurance business. This is a newly created, high-impact role designed for a leader who excels at the intersection of financial analysis, operational efficiency, and long-term value creation.

While you will sit within our centralized Finance organization, you will be deeply embedded in the Medicare Advantage (MA) leadership team. We are looking for a "high-agency" leader who can move beyond simple reporting to actively influence growth levers and unit economics.

As a Director, Strategic Finance (Medicare Advantage), you will:

• Define, Measure, and Optimize Unit Economics: Partner with Actuarial, Growth, and Ops teams to develop a nuanced understanding of unit economics. You will define and track multi-year cohort and plan-level views, while most importantly, working to optimize unit costs and growth levers.
• Lead Planning and Forecasting: Partner with leadership, actuarial and operations to develop annual plans and quarterly forecasts. 
• Drive the Business “Rhythm”: Partner with leadership to review core reporting and initiative progress consistently. You will leverage the monthly close process to ensure alignment with the budget and maintain rigorous scrutiny of ROI for all operational activities. Most importantly, you will ensure insights lead to action.
• Evaluate Strategic Projects: Assess the value of high-stakes programs. Once capital is allocated, you will track these initiatives to ensure they deliver the projected value.

Success in this role looks like:

• In the first 90 days: You have established financial clarity by owning the MA financial model and reporting cadence, providing leadership with a trusted view of performance, cost drivers, and unit economics. 
• In the first 6 months: You have raised the bar on discipline- cost center owners are actively managing spend against plan, and you have become the go-to partner for sophisticated initiative modeling and ROI tracking. 
• In the future: You have built a durable, scalable financial operating model where insights consistently inform investment decisions, enabling the MA business to grow efficiently and achieve sustainable national scale. 

You should get in touch if:

• Financial Expertise: You have 10+ years of progressive finance leadership experience, specifically within healthcare, payer, or insurance environments. 
• Industry Knowledge: You possess deep experience with Medicare Advantage. 
• Strategic Thinking: You can connect complex actuarial data to operational outcomes and have a background in optimizing unit economics and capital allocation. 
• Executive Presence: You have a proven track record as a trusted advisor to senior leadership, able to influence strategy through data-driven storytelling and rigorous financial discipline. 
• Intellectual Agility: You thrive in evolving business models and have the ability to build scalable planning and governance frameworks from scratch.

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.

#LI-REMOTE

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.

At Counterpart Health, we are transforming healthcare and improving patient care with our innovative primary care tool, Counterpart Assistant. By supporting Primary Care Physicians (PCPs), we are able to deliver improved outcomes to our patients at a lower cost through early diagnosis and longitudinal care management of chronic conditions.  

We are seeking a strategic and operationally focused Director, Strategic Finance (Counterpart Health) to serve as a key finance partner during a critical period of growth and commercialization. This is a newly created, high-impact role designed for a finance leader who thrives at the intersection of clinical innovation, software economics, and value-based healthcare.

While you will sit within our centralized Corporate Finance organization, you will be deeply embedded in the Counterpart Health (CPH) leadership team. You will act as a bridge between corporate financial discipline and the entrepreneurial speed of CPH, playing a vital role in balancing ambitious product development and expansion objectives with the operational rigor, margin management, and sustainable value creation necessary for long-term success. We are looking for a "high-agency" leader who can drive accountability and financial responsibility while serving as a thoughtful, strategic thought partner to the business.

As a Director, Strategic Finance, you will:

• Own the Counterpart Health P&L and Multi-Year Model: Directly oversee the financial health of the business unit, ensuring that the financial model accurately reflects the clinical and technology strategy while remaining aligned with Corporate Finance objectives.
• Drive Strategic Growth & Commercialization: Act as a key architect in the go-to-market strategy by modeling pricing, unit economics, and margin profiles for external partnerships and payer relationships.
• Lead Performance Management & Planning: Spearhead the annual planning and long-range strategic forecasting cycles (3-5 year horizon), translating complex operating inputs into actionable financial projections.
• Foster Cross-Functional Accountability: Partner closely with the Counterpart Health leadership team - across Clinical, Product, Engineering, and Growth - to drive cost visibility and help business owners manage spend against plans.
• Inform Capital Allocation: Provide the financial insights necessary for critical technology investment decisions and software capitalization, ensuring resources are deployed toward the highest-value opportunities.
• Establish Scalable Governance: Implement lightweight spend governance and reporting frameworks that provide the discipline needed for a scaling business without sacrificing operational speed.
• Influence Enterprise Strategy: Serve as a trusted advisor, using data-driven storytelling to help the leadership team navigate the complexities of Medicare Advantage reimbursement mechanics and value-based care performance.

Success in this role looks like:

• In the first 90 days: You have established financial clarity by owning the CPH financial model and reporting cadence, providing leadership with a trusted view of performance, cost drivers, and value-based arrangement flow.
• In the first 6 months: You have raised the bar on discipline; cost center owners across CPH are actively managing spend against plan, and you have become the go-to partner for sophisticated customer scenario modeling and shared savings arrangements.
• In the future: You have built a durable, scalable financial operating model where insights consistently inform investment decisions, enabling CPH to grow efficiently and successfully commercialize its clinical technology stack on a national scale.

You should get in touch if:

• Financial Expertise: You have 15+ years of progressive finance leadership experience, specifically within healthcare, payer, or health-tech environments.
• Industry Knowledge: You possess deep experience with value-based care, Medicare Advantage, or risk-based healthcare models (e.g., PMPM performance, shared savings, and downside risk).
• Strategic Thinking: You have the ability to connect financial insights to clinical outcomes and technology strategy, with a background in go-to-market strategy or pricing.
• Executive Presence: You have a proven track record as a trusted advisor to senior leadership, able to influence enterprise strategy and capital allocation through data-driven storytelling.
• Intellectual Agility & Rigor: You thrive in ambiguity and evolving business models, with the ability to build scalable planning and performance management frameworks from scratch.

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.

#LI-REMOTE

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.

Clover Care Services (CCS) is the clinical heart of Clover Health, delivering proactive support and care to our members through our clinical Clover Home Care teams, and quality improvement services to our aligned providers through our Managed Care Organization. We are transforming the healthcare experience by integrating care delivery, provider networks, and clinical programs to improve patient outcomes while managing the total cost of care. CCS functions as a complex, home-based care and managed services organization, leveraging a team-based approach to deliver compassionate, equitable care to members where they are most comfortable: at home.

We are seeking a strategic and operationally focused Director, Strategic Finance to serve as a key finance partner for the CCS organization. This is a newly created, critical role designed for a finance leader who understands the intricate interplay between clinical delivery and business constraints.

While you will sit within our centralized Corporate Finance organization, you will be deeply embedded in the CCS leadership team. You will act as a bridge between corporate financial discipline and the operational realities of a large-scale clinical engine. You will play a vital role during a period of growth and operational maturation, helping drive accountability and financial responsibility while serving as a thoughtful, strategic partner on resource planning, staffing models, and shared KPIs. We are looking for a "high-agency" leader who can navigate the operational realities of the clinical team to ensure our growth is both sustainable and data-driven.

As a Director of Strategic Finance, you will:

• Lead Financial Management & Forecasting: Own the CCS P&L and multi-year financial models. You will drive budget creation, quarterly forecasting, and variance analysis, ensuring financial decision-making is grounded in rigorous data.
• Build Forward-Looking Operational Models: Develop sophisticated models that account for the interplay between clinical delivery and business outcomes, focusing on visit volumes, staffing productivity, and contribution margins.
• Drive Operational Excellence & Process Design: Architect scalable, repeatable, and sustainable operational processes. You will lead workflow mapping and performance tracking to ensure clinical operations are efficient and financially disciplined.
• Master Clinical Cost Drivers: Develop a deep understanding of the cost drivers within clinical operations to provide actionable insights on resource planning, staffing models, and the trade-offs between clinical delivery and business constraints.
• Oversee Vendor Management: Lead contract oversight for clinical and operational partners, conducting ROI evaluations and performance monitoring to ensure high-value delivery.
• Integrate Quality & Economics: Analyze how quality performance and care pathways influence reimbursement and the total cost of care, aligning clinical goals with financial success.
• Foster Cross-Functional Accountability: Partner with Clinical, Network, and Operations leaders to establish shared KPIs and drive cost visibility, empowering them to manage spend effectively without sacrificing care quality.

Success in this role looks like:

• In the first 90 days: You establish financial clarity by owning the CCS financial model and reporting cadence, providing leadership with a trusted view of performance, cost drivers, and resource utilization.
• In the first 6 months: You raise the bar on discipline; you have built repeatable processes for spend management and have developed a deep understanding of clinical workflows to deliver reliable, explainable forecasts.
• In the future: You have built a durable, scalable financial operating model where insights consistently inform staffing and investment decisions, enabling CCS to grow efficiently while delivering high-quality clinical outcomes.

You should get in touch if:

• Financial Expertise: You have 10+ years of progressive finance leadership experience, specifically within healthcare, payer, or provider environments.
• Industry Knowledge: You possess deep experience with Medicare Advantage economics, homecare operations, or MSO financial models.
• Operational Sense: You have a proven ability to build and maintain forward-looking operational models and understand the nuances of clinical delivery.
• Strategic Thinking: You can connect financial insights to clinical outcomes and network performance, with a strong grasp of risk-based healthcare and quality incentive structures.
• Executive Presence: You have a proven track record as a trusted advisor to senior leaders, able to influence strategy and operational decision-making through clear, data-driven storytelling.

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.

#LI-REMOTE

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.