Chairman Programs Lead

cloverhealth; United States; Remote; USD 160,000 - 190,000; Full time

Benefits offered by this job

Equity

Bonuses

401k matching

Medical/Dental/Vision

No-meeting Fridays

Flexible time-off

Remote stipend

Professional development funding

Employee Stock Purchase Plan

Parental leave

Job summary

Clover Health is seeking a Chairman Programs Lead to operate inside the Office of the Chairman and drive the organization’s most important cross-functional initiatives from ambiguity through execution. This role sits at the intersection of strategy, systems design, and execution, acting as a force multiplier to the executive team.

The ideal candidate thrives in undefined spaces, values direct proximity to decision-making, and can lead without formal authority by earning trust and delivering

Qualifications

• 3–10 years of experience in BizOps/consulting or high-trust internal strategy/Chief of Staff-type roles.
• Structured, logical thinking with precise written and spoken communication.
• Proven track record driving complex initiatives to outcomes.
• Energy for ambiguity and low tolerance for bureaucracy.
• Ability to lead without positional authority by earning trust and alignment.

Responsibilities

• Architect strategic programs by translating goals into clearly scoped initiatives with owners and timelines.
• Own initiatives end-to-end from kickoff through measurable outcomes.
• Influence and align stakeholders across levels without relying on positional authority.
• Convert ambiguity into action by building playbooks and rebuilding coordination systems.
• Manage cross-team and external-partner projects, aligning internal readiness to external dependencies.

Skills

Structured thinking

Executive communication

Program management

Ambiguity tolerance

Leading without authority

Job description

Role overview

A health insurance company is hiring a Chairman Programs Lead to operate inside the Office of the Chairman and drive the organization's most important cross-functional initiatives from ambiguity through execution. The role sits at the intersection of strategy, systems design, and executional rigor, acting as a force multiplier to the executive team and orchestrating work across organizational boundaries. It is suited to a high-agency operator who thrives in undefined problem spaces and values direct proximity to decision-making.

Responsibilities

• Architect strategic programs by translating high-level goals into clearly scoped initiatives with crisp interfaces, dependencies, owners, and timelines.
• Own initiatives end-to-end from kickoff through measurable outcomes, maintaining strategic altitude and execution detail without losing either.
• Influence and align stakeholders across levels and functions without relying on positional authority, driving accountability through clarity rather than escalation.
• Convert ambiguity into action by building playbooks where none exist, forcing priorities when unclear, and rebuilding coordination systems when they break down.
• Manage projects that span internal teams and external partners such as vendors, regulators, and strategic collaborators, aligning internal readiness to external dependencies.

Requirements

• Three to ten years of experience at a top-tier consulting firm, in BizOps at a technology company, or in a high-trust internal strategy or Chief of Staff-type role.
• Structured, logical thinking with precise written and synthesized verbal communication.
• Demonstrated record of driving complex initiatives to outcomes, not just advising on them.
• Energy for ambiguity, low tolerance for bureaucracy, and motivation by direct proximity to decision-making and value creation.
• Ability to lead without positional authority by earning trust and alignment through clarity, quality, and velocity.

Nice to have

• Background designing or scaling coordination mechanisms that improve cross-team execution.
• Familiarity with healthcare, insurance, or other regulated industries.

Benefits and work setup

• Base salary range of $160,000 to $190,000, plus equity, performance-based bonuses, and 401k matching.
• Comprehensive medical, dental, and vision coverage.
• Mental-health initiatives such as no-meeting Fridays, monthly company holidays, and a flexible time-off policy.
• Remote-first culture with reimbursement for office setup and a monthly cell phone and internet stipend.
• Professional development funding, mentorship, an Employee Stock Purchase Plan, and paid parental leave.