Chief Operating Officer
Milwaukee, WI 
Posted 10 days ago
Job Description
Chief Operating Officer
Milwaukee, WI
Open Sky Education

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Position: Chief Operating Officer

Reports To: Chief Executive Officer/Executive Chair

Company Overview: Open Sky Education is an entrepreneurial not-for-profit organization in tireless pursuit of a full and lasting education for all children. Open Sky Education works to ensure that world-class academics, character formation and faith-based educational choices are accessible and affordable for all. We support and manage a national growing network of learning environments, including , , , Day Two Facilities and the .

Position Overview: The COO will provide executive leadership, strategic direction and managerial oversight for all operational systems and processes that directly impact or support the educational mission of the organization. The COO will inspire and drive the development and creation of new protocols, processes and procedures in areas where such development is needed, as well as ensure the logistical supportability of these initiatives. He/she will also refine and enhance current operational systems with the intent to maximize efficiency and effectiveness throughout the organization, while ensuring all activities and agencies are mission and culturally aligned, vision focused, and metric driven. The COO will also instill a strong organizational culture by managing communications and information flow, fostering team engagement and ensuring clarity of purpose and priorities across all functions. The COO's driving purpose is to expand time for our educators to build authentic relationships with students, parents and co-workers, contextualize programming for the children and families we serve, and deliver consistent and continual improvement of both educational and financial results. The leadership and development of best in class operational systems will free up organizational time and energy for continual improvement and will lay the foundation for strategic multi-site scaling initiatives.

Core Responsibilities:
  • Vision
    • Lead the Executive Team and National Board to create annual goals and strategic priorities in alignment with our mission and vision
    • Ensure improvement priorities and initiatives align with qualitative and quantitative data
    • Anticipate future trends and conditions and lead the team to innovate accordingly
    • Support communication of the vision and strategies to motivate and align stakeholders
    • Define strategies and processes necessary for multi-site scaling of new schools and before and after-care sites
  • Serving Leadership
    • Lead hiring managers to recruit and develop high-functioning teams deeply aligned in culture, mission and vision
    • Build authentic relationships and ensure excellent internal communications with all key stakeholders
    • Ensure all team members understand their role (including clear job descriptions and evaluation processes) as well as how it fits within the overall organization
    • Empower team members within clear boundaries of our purposeful (strategic) plan and decision rights grid
    • Raise the bar for excellence and celebrate progress
    • Remove obstacles, problem solve and help secure the necessary tools for success
    • Integrate cross-functional and multi-level teamwork ensuring alignment and efficiency
    • Manage organizational meeting schedules and agendas
  • Purposeful (Strategic) Planning
    • Lead, manage and coordinate the annual purposeful planning process across the entire organization building ownership and alignment of all key stakeholders
    • Ensure alignment between the purpose (mission), path (values), picture (vision), plan (strategic initiatives) and performance indicators (metrics) across the entire organization
    • Develop and oversee the implementation of a clear decision rights grid
    • Assist the CFO to drive fiscally responsible budgeting processes
  • Plan Execution
    • COO shall have direct management responsibility of all Support Team Division Leaders except for Facility and Finance divisions (who report to the CFO)
    • Collaborate with the OSE Executive Team to manage Purposeful (Strategic) Plan execution maintaining an eye for excellence and instilling a sense of appropriate urgency
      • Create and implement all systems, structures and communications patterns necessary to ensure that the Purposeful Plan drives organizational activity
      • Practice data-based performance management in all areas including the production of regular dashboards measuring outputs, leading indicators and inputs (model execution)
      • Monitor execution of our plans against performance goals
    • Implement a systems approach to scaling, productivity optimization and continuous improvement
    • Automate core repetitive processes throughout all divisions of OSE
      • Design, implement and document best-practice business processes and procedures to produce efficiency and excellence in execution
      • Fully document process flows, descriptions and decision rights
      • Eliminate waste, redundancy or negative variance while promoting positive variance
      • Simplify to grow efficiency
      • Implement adequate training, monitoring of implementation and evaluation for accountability
    • Ensure compliance with all external and internal requirements across the organization
    • Oversee the creation and implementation of all aspects of our infrastructure (including systems and people) needed to support multi-site scaling of new operations
    • Ensure proper governance and oversight
      • Provide board support for our National and Regional boards
      • Ongoing monitoring of operational performance and continually improving operational performance
      • Establishing policies that promote company culture and vision
      • Oversee organizational governance activities

Key Past Experiences:
  • 5+ years in a Chief Operating Officer position
  • Executive level leadership role in a rapidly scaling, multi-site organization
  • Successful development and execution of complex strategic plans across multiple disciplines, ensuring collaboration and cooperation among key stakeholders
  • Building, leading and managing high-functioning teams

Key Characteristics:
  • Personal Strengths
    • Has passion for closing the achievement, character formation, and access to faith-based education gaps for a rapidly growing number of children
    • Embraces the core values of the organization
    • Exemplifies Serving Leadership by continually raising the bar, confronting the brutal facts, and inspiring the leadership team to achieve beyond their own expectations
    • Thinks strategically and imaginatively
    • Enjoys tackling challenges and overcoming obstacles.
    • Anticipates potential problems/issues before they occur and puts together preventive strategies.
    • Has high degree of resilience.
    • Builds productive relationships that support a culture of "team and family"
  • Professional Strengths
    • Able to lead multiple complicated and intense projects
    • Has strong communication skills
    • Excellent leadership, talent assessment, coaching and mentoring skills.
    • Able to select, develop and manage high-performing and driven leaders
    • Capable of delegating well and effectively monitoring the progress of team members
    • Strong analytic skills; uses data to monitor organizational progress, make decisions and predict possible future outcomes
    • Resourceful; exhausts networks and partnerships to ensure "best options" are explored.
    • Expert in change management
    • Thrives at developing and implementing key systems with consistency to meet specific organizational goals across all levels and functions of the organization
    • Experience in an education setting will be a plus
  • 5+ years in a Chief Operating Officer position
  • 4-6 years in an educational leadership/administrator role
  • Executive level leadership role in a rapidly scaling, multi-site organization
  • Successful development and execution of complex strategic plans across multiple disciplines, ensuring collaboration and cooperation among key stakeholders
  • Building, leading and managing high-functioning teams
  • Previous experience in a multi-state organization preferred
  • Experience managing others and managing a team of direct reports
  • Proven leadership skills with well-rounded experience in the education industry
  • Strong proficiency in MS Word, Excel, PowerPoint, and Outlook
  • Technology savvy; experience using non-profit accounting software is a plus
Educational Background:
  • Bachelor's degree with an emphasis in Business and/or Education
  • MBA or comparable graduate degree desired

Anticipated Start Date: Position is open immediately

Salary and Benefits: Compensation based on experience and discussed with finalists


Job Summary
Start Date
Employment Term and Type
Regular, Full Time
Required Education
Bachelor's Degree
Required Experience
5+ years
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