Chief of Staff to the CEO

Chief of Staff to the CEO

Position Title: Chief of Staff to the CEO

Reports To: Chief Executive Officer

Office: Hybrid; New York City preferred; some travel

Job Summary "Who We are Looking For"

At Per Scholas, our mission moves fast and keeping that momentum focused, collaborative, and decisive takes an extraordinary orchestrator. We are looking for a seasoned facilitator and strategic operator with 10–15 years of senior leadership experience to step into the role of Chief of Staff to the CEO. Partnering closely with our Chief Executive Officer and National Leadership Team, you will design the cadence of how our senior executives collaborate, make bold decisions, and execute enterprise priorities. From facilitating critical leadership forums to steering board governance and driving complex change management, your leadership will ensure our executive team operates with clarity, trust, and shared accountability—accelerating our national impact on the future-ready workforce. 

What You'll Do

Meeting Design & Facilitation

• Design and facilitate National Leadership Team meetings, quarterly planning sessions, and executive retreats: agendas, pre-reads, decision framing, and clear documentation of decisions and owners.
• Facilitate high-stakes conversations, including strategy trade-offs, resource decisions, and cross-functional conflicts, so every voice is heard and the group reaches clear, timely decisions.
• Bring structure and proven facilitation methods (decision-rights frameworks, pre-mortems, retrospectives) to make leadership time more effective.
• Partner with the CEO and Board Chair on board meeting design and facilitation, including executive sessions and committee meetings as applicable.

Team Effectiveness

• Assess and strengthen how the leadership team works: norms, communication, accountability, and trust. Encourage a culture of candid, constructive feedback to and among senior leaders.
• Help new executives integrate quickly, especially leaders joining the team during the 2027 transition.
• Serve as a trusted sounding board to the CEO, giving honest perspective on organizational health, team dynamics, and leadership effectiveness.

External Engagement & Representation

• Help the CEO prioritize and prepare for high-value external engagements with employers, funders, policymakers, and partners. Work with the relevant executives so the CEO's external presence advances organizational priorities and key relationships.
• Own preparation for the CEO's external meetings: briefings on attendees and relationship history, meeting objectives, key messages, and specific asks.
• Attend high-value external meetings with the CEO as appropriate. Capture commitments and next steps, and drive follow-up with accountable owners.
• Keep internal leaders up to speed. Brief relevant executives and teams before and after key external engagements so relationship owners have context, commitments made in the CEO's name are honored, and Per Scholas speaks with one voice.
• Represent the CEO in external and internal meetings as needed. Speak credibly to Per Scholas priorities, and bring back clear readouts and recommendations.
• Serve as a close partner to the Strategic Communications team on the CEO's external voice and visibility, helping 

CEO Operating Rhythm & Executive Operations

• Own the CEO’s operating rhythm: priorities, calendar strategy, meeting cadence, and follow-through on commitments.
• Lead the Executive Operations team, ensuring seamless support for the CEO and National Leadership Team.
• Translate strategic and annual plan into operational priorities. Track ongoing enterprise priorities and decisions; surface risks and blockers early and drive resolution.

Board & Governance

• Manage board and committee preparation, materials, and follow-up in partnership with the CEO and Board leadership.
• Ensure strong coordination between the National Board, the CEO, and the National Leadership Team.

Change Management & Special Initiatives

• Lead change management for organization-wide initiatives, including leadership transition and structural changes and high priority communications, ensuring clear sequencing, stakeholder engagement, clear accountability, and communication.
• Identify potential gaps and advise the CEO and NLT on how to ensure all aspects of a particular change are both named and executed.
• Lead CEO-sponsored special initiatives with clear ownership, timelines, and accountability, in partnership with the relevant executives.
• Partner with the Chief Marketing Officer and Chief People Officer to ensure major organizational changes are supported by clear, coordinated, and effective internal communications.

What You'll Bring To Us

• 10–15 years of progressive experience, including senior roles in strategy, operations, organizational effectiveness, or as Chief of Staff to an executive.
• Extensive professional experience designing and facilitating executive-level meetings, retreats, and strategic planning sessions.
• Proven track record leading complex, multi-site or national change management initiatives with clear stakeholder communication and sequencing.
• Strong presence, credibility, and emotional intelligence to work collaboratively with board members, senior executives, and cross-functional partners.
• Demonstrated ability to provide candid, constructive feedback with tact and diplomatic judgment.
• Polished external representation skills with corporate partners, funders, and civic leaders.
• Exceptional judgment, discretion, and emotional intelligence handling highly confidential executive matters.
• Outstanding written, verbal, and project management skills with high attention to detail.
• Demonstrated commitment to equity, inclusion, and mission-driven work (experience in workforce development or education preferred).

Per Scholas offers a competitive salary $165,000 - $190,000 depending on experience, location and a comprehensive benefits package, including health, dental, and vision coverage, a retirement match, generous paid time off, and professional development opportunities.