Job Description:

The CPO provides executive leadership across a diverse continuum of services supporting individuals and families with complex needs, with direct oversight of 116 programs, approximately 1,003 program FTEs, and an annual operating revenue budget of approximately $133.4 million.  Leading a team of senior program, service, and clinical executives, the CPO is accountable for strengthening operational and financial l performance, service integration, leadership capacity, quality and compliance, and long-term sustainability while ensuring services remain grounded in Open Sky’s mission, values, whole person health framework, and commitment to person-centered, trauma-informed care.

As an enterprise leader, the CPO brings a strategic and systems-oriented perspective to organizational decision-making, using data, operational insight, and strong executive judgment to anticipate challenges, identify opportunities, and drive meaningful and sustainable results. The CPO plays a critical role in developing senior leaders, strengthening accountability, navigating organizational change, and creating greater connection and consistency across service lines.

The CPO also serves as a highly visible representative of Open Sky with funders, regulators, community stakeholders, peer organizations, and strategic partners. In collaboration with the President & CEO and executive leadership, the CPO advances relationships and opportunities that strengthen Open Sky’s impact and position the organization for thoughtful innovation, strategic growth, partnerships, service expansion, mergers and acquisitions, and long-term sustainability.

Executive Responsibilities

Strategic Vision, Leadership & Executive Partnership

• Serve as a trusted executive thought partner to the President & CEO and Executive Leadership Team, helping shape organizational strategy, enterprise priorities, and long-term direction.
• Provide steady executive leadership through periods of change, growth, and complexity, ensuring continuity, mission alignment, and disciplined execution of organizational priorities.

• Translate enterprise strategy into clear operational priorities, performance expectations, and accountable systems across the service portfolio.
• Partner with Human Resources and service leaders to anticipate and address workforce needs, organizational structure, leadership capacity, staffing models, retention, succession planning, and other workforce factors affecting service quality, operational performance, and organizational sustainability.
• Partner with the President & CEO and executive leaders in engagement with the Board of Directors including participation in Board meetings, committees, reporting, and strategic discussions.

Program Operations, Integration, & Service Excellence

• Provide executive leadership and accountability for Open Sky’s broad continuum of programs and services, ensuring effective, integrated, responsive, and high-quality services aligned with the organization’s mission, values and service frameworks.
• Establish clear expectations for program performance and work through senior service leaders to drive consistent execution, accountability, and continuous improvement across the service portfolio.
• Strengthen integration across service lines and administrative functions to improve continuity, coordination, quality, and experience of individuals served, families, employees, and partners.
• Maintain meaningful visibility across programs and communities served, engaging regularly with program leaders, employees, individuals served, and other stakeholders to inform executive decision-making and remain connected to operational realities. 

Financial Performance and Accountability

• Hold executive accountability for the financial performance and sustainability of the service portfolio, partnering closely with the Chief Financial and Operating Officer to ensure operating decisions, resource allocation, budget performance, and service-line strategies support organizational financial objectives and long-term sustainability.
• Use financial, operational, and performance data to identify trends, variances, opportunities, and risks, and drive timely action to improve results.
• Establish financial accountability among service leaders by setting clear expectations, monitoring performance, and ensuring leaders in understanding and actively manage the operational and financial impact of their decisions.

Quality, Compliance, Risk, and Performance Improvement

• Champion data-informed performance improvement, outcomes measurement, and evidence-based and promising practices that strengthen service quality and outcomes for individuals served.
• Partner closely with the Chief Quality and Compliance Officer to ensure service operations, risk management, performance improvement, and regulatory readiness meet organizational quality, compliance, and service excellence expectations.
• Advance a culture of, ethical practice, accountability, risk awareness, continuous quality improvement and readiness for audits, surveys, accreditation reviews, contractual obligations, and regulatory requirements.
• Partner across Quality, Compliance, Clinical, Finance, Human Resources, and program leadership to proactively identify, escalate, and mitigate operational, clinical, workforce, compliance, financial, and reputational risk.

People, Culture, and Leadership Development

• Build and lead a high-performing senior program leadership team, establishing clear expectations, decision rights, performance accountability, succession planning, leadership development, and shared ownership for organizational outcomes.
• Develop the capacity and effectiveness of senior leaders through coaching, candid feedback, performance management, succession planning, and opportunities for continued leadership growth.
• Foster a culture of collaboration, transparency, accountability, and constructive challenge in which leaders communicate openly, address issues directly, and work across organizational boundaries to achieve shared priorities.
• Advance diversity, equity, inclusion, and belonging through leadership practices, talent decisions, program access, service design, employee experience, and community engagement.

Innovation, Growth & External Relationships

• Serve as a senior representative of Open Sky with funders, regulators, community stakeholders, peer organizations, government partners and other external constituencies to strengthening relationships, and advancing organizational priorities in collaboration with the President & CEO and executive leadership.
• Partner with the Vice President of Business Development, President & CEO, and other executive leaders to identify, evaluate, and advance mission-aligned growth opportunities, including strategic partnerships, service expansion, new program models, grants, mergers, and acquisitions. 
• Build and sustain strong community partnerships that advance Open Sky’s mission, strengthen connections to local resources and systems of care, and ensure the organization remains visible, engaged, and responsive to the needs of the communities it serves.
• Evaluate growth opportunities through an enterprise lens, considering mission alignment, community need, operational readiness, workforce capacity, financial sustainability, quality, risk, and long-term organizational impact.
• Perform other duties as assigned.

Leadership Competencies

• Strategic and Systems Leadership: Thinks enterprise-wide, connects strategy to execution, and builds structures that support consistent, integrated, high-quality service delivery.
• Change Leadership & Organizational Resilience: Provides steady, values-driven leadership, strengthens continuity across programs, and helps leaders navigate change and complexity with clarity, adaptability, and confidence.
• Operational and Financial Accountability: Establishes clear performance expectations, uses data to monitor and guide decisions, and partners with leaders to improve outcomes, productivity, financial performance, and sustainability.
• Integrated Service Culture: Promotes collaboration across service lines, reduces silos, and advances a cohesive organizational culture grounded in relationships, opportunities, wellness, trauma-informed care, and whole person health.
• Risk, Compliance, and Quality Stewardship: Anticipates and mitigates operational, clinical, financial, compliance, and reputational risk while promoting continuous quality improvement and readiness for regulatory, contractual, and accreditation expectations.
• Inclusive and Mission-Driven Leadership: Models humility, curiosity, transparency, ethical decision-making, and a deep commitment to diversity, equity, inclusion, belonging, and service accessibility.
• Talent and Leadership Development: Builds, coaches, and supports senior leaders; encourages shared accountability; and fosters an environment where staff are equipped to learn, grow, and lead effectively.
• External Partnership and Growth Orientation: Represents the organization effectively with external stakeholders and brings a thoughtful, research-informed approach to program growth, partnership opportunities, and mergers or acquisitions when aligned with mission and strategy.
• Judgment, Integrity & Executive Accountability: Demonstrates sound judgment, ethical leadership, transparency, discretion, and personal accountability; navigates complex and sensitive matters with appropriate professional boundaries and consistently acts in the best interests of the organization and individuals served.

Experience & Qualifications

• Master’s degree in health and human services, behavioral health, developmental disabilities, public administration, social work, business administration, or a related field required.
• Minimum of ten (10) years of progressively responsible leadership experience within complex health and human services organizations, including significant senior executive experience with responsibility for multi-service operations, senior leaders, financial performance, quality and compliance, and organizational strategy.
• Demonstrated success leading large complex service portfolios, building high-performing teams, leading organizational change, and translating strategic priorities into measurable operational results.
• Demonstrated executive-level financial acumen and accountability for significant operating budgets, including budget strategy, financial performance, resource allocation, service-line viability and long-term sustainability.
• Programmatic and/or clinical experience required. A clinical license is not required; however, the successful candidate must demonstrate a strong understanding of evidence-based, trauma-informed, person-centered, and clinically informed service delivery and the ability to partner effectively with clinical, nursing, and medical leaders.
• Demonstrated experience navigating complex regulatory and funding environments, including contractual requirements, accreditation expectations, quality improvement, risk management, and audit and survey readiness.
• Demonstrated knowledge of Massachusetts health and human services systems, regulatory agencies, funding structures, and provider environments strongly preferred.
• Exceptional executive communication, presentation, and relationship-building skills, with the ability to engage effectively with the President & CEO, executive leadership, Board of Directors, employees, individuals served and families, funders, regulators, and government partners and community stakeholders.
• Ability and commitment to maintain meaningful visibility across programs and communities served. Regular travel to programs and administrative locations throughout the organization’s service area is expected.

Pay Range:

$250,000 - $300,000

About Us:

At Open Sky Community Services, we open our doors, hearts, and minds to the belief that every individual, regardless of perceived limitations, deserves the chance to live a productive and fulfilling life.

Open Sky is on an anti-racist journey, committed to learning, living, and breathing inclusion, opportunity, diversity, racial equity, and justice for ALL.

At Open Sky, you’ll join over 1,300 compassionate and highly trained professionals who put innovative, evidence-based practices to work in ways that positively impact our communities across Central Massachusetts and beyond.

As a trauma-informed organization, Open Sky strives for transparency and sensitivity to the experiences of those we interact with. Self-care is encouraged, and we are committed to providing a positive work culture that is focused on continuous learning and the value of diverse perspectives.

Open Sky is proud to be an industry leader in pay and benefits. Open the Door to Possibility and begin your career with Open Sky today!

Benefits of Working for Open Sky Include:

• Excellent Supervision (Individual and Group), Professional Development, and Training Opportunities
• Generous paid time off plan – you start with 29 days (almost 6 weeks!) in your first year, including 12 paid holidays. Increases to 32 days in your 2nd year, and the current maximum is 43 days (OVER 8 WEEKS!)
• We pay for your higher education!  Ask about our Tuition Reimbursement Program, and reimbursement for a variety of Human Services certifications.
• Medical, Dental and Vision Insurance with Prescription Plan
• 403b Retirement Plan with Employer Match
• Life Insurance (100% Employer-Paid)
• Eligible employer for the Public Student Loan Forgiveness Program
• And more! 

Open Sky celebrates diversity and is proud to be an Equal Opportunity Employer. In compliance with federal and state employment opportunity laws, qualified applicants are considered for all positions without regard to race, gender, national origin, religion, age, sexual orientation, disability, veteran, or disabled Veteran status.