Chief Operating Officer Insurance Jobs (NOW HIRING)

This is an excellent opportunity for a Chief Operating Officer (40 hours/week) at our Administration Offices in Milwaukee, WI and remote.

• Company contribution toward medical insurance deductible
• Generous Paid Time Off
• 12 Days of Holiday Pay
• Immediate 401(k) Vesting with up to 6% company contribution
• Paid Parental Leave
• Tuition Assistance
• Public Service Loan Forgiveness Program

PPWI’s compensation philosophy is rooted in equity. Starting offers are determined by both the candidate’s applicable experience and internal equity. The Chief Operating Officer pay starts from $179,878 annually. Additional $1.50 per hour for bilingual (English/Spanish).

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

Carries out supervisory responsibilities in accordance with the organization’s policies and applicable laws. Responsibilities include interviewing, hiring, and training employees; planning, assigning, and directing work; appraising performance; rewarding and disciplining employees; addressing complaints and resolving problems.

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.

• Predominantly sedentary with intermittent (15% or less of time in typical week) standing and walking
• Repetitive motions of hands and wrists related to typing on a keyboard and using a mouse
• May require lifting and/or carrying objects weighing up to 10 pounds
• Vision, speaking, and hearing abilities required

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.

• 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.

ESSENTIAL DUTIES & RESPONSIBILITIES Healthcare, Operations, and Compliance

• Provide executive leadership for PPWI’s healthcare operations and business initiatives, advancing a sustainable operating model that expands access to care and supports the full mission.
• Lead organization-wide operational planning and performance across Patient Services, Security, IT, and Facilities, including development and oversight of operating budgets.
• Establish, operationalize, and oversee healthcare compliance and quality systems to ensure adherence to all federal, state, and local regulations and PPFA accreditation standards.
• Use data, metrics, and performance analysis to drive operational improvements, infrastructure enhancements, and efficient workflows; establish clear measures of success and reporting mechanisms for leadership, staff, and the Board.
• Produce clear, concise operational reports, evaluations, and narratives demonstrating performance for internal and external stakeholders.
• Identify, evaluate, and advance strategic partnerships—within and beyond PPFA—to strengthen service delivery, financial sustainability, and mission alignment.
• Oversee vendor strategy and contract management, ensuring compliance, performance monitoring, and execution of related contracts, MOUs, and business agreements, including advancing equitable contracting practices.
• Ensure all PPWI facilities are safe, compliant, efficient, and reflect the dignity patients and staff deserve; ensure completion of required training related to customer service, quality assurance, HIPAA, OSHA, CLIA, and related compliance standards.

National Operational Infrastructure

• Serve as PPWI’s executive lead with national operational partners and PPFA-supported infrastructure (including health systems, IT platforms, and shared service entities), holding partners accountable to PPWI’s operational needs while ensuring PPWI meets its obligations.
• Represent PPWI as a technical expert on appropriate national boards, committees, and advisory bodies related to healthcare operations and infrastructure.

Security and Information Technology

• Provide executive oversight and accountability for the agency’s physical security strategy, ensuring a high standard of safety for people, facilities, and operations.
• Oversee enterprise technology infrastructure and information security systems to support high-quality care, data privacy, and operational effectiveness.
• Lead, support, and direct the HIPAA Privacy Officer to ensure PPWI’s HIPAA Security Program is documented, reviewed, enforced, and updated in accordance with applicable regulations.

Leadership and Organizational Engagement

• Serve as a strategic thought partner to the President & CEO and a visible, trusted leader across the organization.
• Foster strong, collaborative, cross‑departmental relationships to advance PPWI’s strategic goals.
• Mentor and develop leaders to strengthen organizational capacity and succession.
• Regularly communicate progress toward strategic and operational goals to leadership, staff, and the Board; attend Board and committee meetings as a subject‑matter expert, as needed.

Perform other duties as assigned.

Any job offer will be contingent upon the results of a background investigation.

PPWI is an equal opportunity employer committed to diversity in the workplace.