Remote Chief Operating Officer Insurance Jobs (NOW HIRING)

Purpose of Position:

The Chief Operating Officer (COO) is a senior executive and strategic thought partner to the President & CEO, with enterprise-wide accountability for safe, high-performing, and compliant healthcare and security operations for Planned Parenthood of Wisconsin, Inc. (PPWI) and its affiliated organizations. As a key member of the executive leadership team, the COO collaborates closely with the CEO and Board of Directors to shape mission-centered business strategies, organizational priorities, and long-term operational viability.

The COO sets the strategy and direction for PPWI’s healthcare operations and infrastructure, ensuring the delivery of high-quality patient care, exceptional customer service, strong security, and a sustainable health system model. The COO establishes and maintains systems that ensure compliance with all regulatory, accreditation, and risk management requirements. All strategies and decisions are developed through an equity lens, advancing PPWI’s commitment to health equity, dignity, and belonging for patients, staff, and communities.

Knowledge, Skills and Abilities:

Executive & Strategic Leadership

• Demonstrated experience serving as a senior executive leader and trusted thought partner to the CEO and governing board.
• Proven ability to lead large, complex organizations through growth, change, and risk.

Healthcare Operations & Compliance

• Deep knowledge of healthcare delivery systems, clinical operations, regulatory compliance, and accreditation standards.
• Demonstrated success establishing and maintaining quality, compliance, and risk management systems.

Business & Financial Acumen

• Demonstrated executive-level business acumen within complex healthcare and/or nonprofit environments, with direct accountability for budgeting, long-range financial planning, forecasting, resource allocation, and enterprise performance management. Proven ability to align operational priorities with financial strategy to ensure sustainability, margin optimization, and mission impact.

• Leverages data analytics, financial modeling, and key performance indicators to drive strategic and operational decision-making. Translates complex financial and operational data into actionable insights that improve efficiency, optimize reimbursement and revenue cycle performance, manage cost structures, and support long-term organizational viability.

Infrastructure, Technology & Security Leadership

• Experience overseeing enterprise technology systems, health information systems, and data security in a regulated environment; EPIC experience preferred.
• Knowledge of best practices in physical security of people and facilities.

People & Team Leadership

• Proven ability to build, develop, and lead high-performing, cross-functional teams.
• Demonstrated commitment to mentorship, leadership development, and collaborative culture.

Equity-Centered Leadership

• Demonstrated leadership advancing diversity, equity, inclusion, and belonging, including applying an equity lens to operational and business decisions.

External Partnerships & Vendor Management

• Skill in developing strategic relationships with external partners, vendors, and national organizations.
• Strong contract negotiation and vendor oversight experience.

Technical Skills

• Proficiency with Microsoft Office and enterprise reporting tools.

Education and/or Experience:

• Advanced degree in healthcare administration or related field

• Minimum of seven (7) years of senior operational leadership experience, including responsibility for multi‑site operations, regulatory compliance, and enterprise‑level systems within a healthcare or similarly regulated environment.

• An equivalent combination of education and experience from which comparable knowledge and abilities can be acquired may be considered.

Supervisory Experience: 

Physical Requirements:

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of the job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

This position is:

• Predominantly sedentary with intermittent (15% or less of time in typical week) standing and walking

Other Physical Requirements:

• Repetitive motions of hands and wrists related to typing on a keyboard and using a mouse

Vision, Speaking, and Hearing Abilities:

• Speaking
• Hearing

May require lifting and/or carrying objects weighing:

• Up to 10 pounds

Working Conditions:

This position is generally performed in an office environment but involves occasional interruptions. The work environment characteristics are representative of those an employee encounters while performing the essential functions of this position. Reasonable accommodations, however, may be made to enable individuals with disabilities to perform said essential functions.

Other environmental and/or working conditions:

• Normal noise levels

Working Hours: 

• Occasional evening and/or weekend hours may be necessary.
• Must be available by phone to respond to after-hours situations requiring leadership action.

Driving Conditions:

This position requires traveling statewide, therefore a valid driver’s license and auto insurance in accordance with agency liability standards is required. Must have transportation.