Strong fit for seasoned facilitators who design executive collaboration cadences and drive enterprise priorities, with a preference for candidates based in New York City who thrive in hybrid work arrangements.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Per Scholas via Greenhouse
ABOUT PER SCHOLAS:
For 30 years, Per Scholas has been on a mission to drive mobility and opportunity in the ever-advancing technology landscape by unlocking the untapped potential of individuals, uplifting communities, and meeting the needs of employers through rigorous tech training. By teaming up with dynamic employer partners, ranging from Fortune 500 companies to innovative startups, we're forging inclusive tech talent pipelines, fulfilling an ever-increasing need for skilled talent. With national remote training and campuses in 20+ cities and counting, Per Scholas offers no-cost training programs in the most sought-after tech skills, spanning Cloud, Cybersecurity, Data Engineering, IT Support, Software Engineering, and more. To date, 30,000+ individuals have been trained through Per Scholas, propelling their professional trajectories into high-growth tech careers with salaries three times higher than their pre-training earnings. Learn more by visiting PerScholas.org and follow us on LinkedIn, X, Facebook, Instagram, and YouTube.
Per Scholas candidates must reside in one of the following states, provided the position does not carry a specific office location requirement: AZ, CA, CO, FL, GA, IL, IN, KS, MD, MA, MI, MO, NC, NJ, NY, OH, PA, TX, WA, WI.
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.
Benefits & Perks
Per Scholas offers a comprehensive benefits package designed to support your health, financial well-being, and overall quality of life!
Holidays & PTO: Full-Time Per Scholas team members enjoy over 40 days of paid time off each year through a mix of holidays, vacation, and sick/personal time! All employees are eligible for Holiday pay upon hire (a total of 22 holidays annually, including a week off for Independence day and a week before the New Year). Full-Time Benefits Eligible employees also receive 80 Wellness Hours to use for Sick, Safe, or Personal reasons and accrue Vacation at a rate of 8 hours at the beginning of every month, supporting rest, recharge, and work-life balance. Vacation accruals increase with tenure. Part-time employees are afforded time off on a prorated basis and in accordance with local requirements.
Comprehensive Medical Coverage: Benefit eligible employees can choose from multiple medical plans through Cigna or Kaiser Permanente (where available), with options to fit your needs. Eligible employees also have access to a Health Reimbursement Account (HRA) that reimburses eligible out-of-pocket expenses, up to $4,000 for individuals and $8,000 for families.
Dental and Vision Insurance: Eligible employees can select from two dental plan options and a vision plan. Employees who waive medical coverage receive employer paid dental and vision premiums.
Retirement Savings: 401(k) plan with a current 100% employer match on contributions up to 6%, eligible employees are offered entry and full vesting after 90 days with the company.
Employee Assistance Program (EAP): Free, confidential, 24/7 access to counseling, legal support, and financial resources for employees and their household members
Parental Leave: Eligible employees are offered up to 6 weeks of 100% paid parental leave to support employees as they welcome a new child and bond with their family.
Additional Benefits & Perks: Eligible employees have access to employer-paid life and AD&D Insurance, as well as employer-paid short-term disability coverage, with the option to elect additional life coverage and long-term disability insurance. Flexible Spending accounts are available for healthcare, dependent care, and commuting expenses. Per Scholas also offers a range of voluntary benefits, including: Accident, Critical Illness, Hospital Indemnity, Legal Services, and Pet Insurance. Additional resources include healthcare concierge support, financial wellness tools, and employee discount programs.
QUESTIONS?
If you have any questions about this role, please feel free to email our Talent team at jobs@perscholas.org. We look forward to viewing your application!
Equal Employment Opportunity
We're proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, race, color, religion, sex, sexual orientation, gender identity or national origin.
PII Policies
Non-Discrimination Policy
Source: Per Scholas careers (Greenhouse)