Steven Westlake

Executive Leadership Partner and Founder of Pinnacle Leadership Group LLC

Steven Westlake brings over 30 years of distinguished executive experience to the table, shaped by his diverse roles as Superintendent, Principal, and HR Director within leading educational organizations. His multifaceted perspective uniquely positions him to enhance the stability and performance of independent schools.

Core Expertise

Steven’s work centers on three foundational pillars vital to private educational institutions:

• Effective Governance

• Organizational Stability

• Leadership Capacity

Founded to provide confidential, high-level counsel, Pinnacle Leadership Group supports Heads of School, Principals, and Boards in navigating complex challenges through:

• Mitigating High-Stakes Personnel Risk
  Drawing from his HR expertise, Steven develops competitive retention strategies and ensures compliance with robust administrative and legal practices.

• Strengthening Strategic Governance
  Expert guidance to Boards and executive teams on fiduciary responsibilities, strategic alignment, and optimizing the Head of School–Board relationship.

• Building the Leadership Pipeline
  Utilizing proven leadership frameworks like the AIRS Initiative to transform high-potential faculty into resilient, high-capacity administrators.

Why Partner with Steven?

Steven excels at translating complex operational challenges into clear, actionable strategies that protect your school’s reputation and secure long-term financial health. His partnership provides the executive bandwidth essential for shifting your institution from reactive problem-solving to proactive, visionary leadership.