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Leadership Grounded In Love


City Year San Jose / Silicon Valley



Position Overview

City Year San Jose / Silicon Valley is seeking a Chief of Staff to provide leadership and oversight for City Year’s day-to-day functions and staff. A trusted advisor and thought partner for the Executive Director, the Chief of Staff will act as gatekeeper, problem solver, tactician, and strategic partner to develop and meet site goals and advance City Year’s mission. The Chief of Staff will ensure the successful operation of the site by managing the Executive office, nurturing team leadership & staff development, monitoring and developing budgets, creating and implementing policies & procedures, providing Board management and support, building and managing relationships on behalf of the Executive Director, and completing special projects and initiatives . The ideal candidate is a skilled and flexible prioritizer who can handle complex situations and multiple responsibilities simultaneously. They build relationships intentionally and sustainably, and possess a natural ability to inspire others to action. 




Executive Office Management & Team Leadership

  • Supervise all administrative staff, providing coaching and performance reviews that contribute to their development as skilled professionals.

  • Manage workflow of the Executive Office and Senior Leadership Team.

  • Establish and communicate site-wide policies and procedures on behalf of City Year San José/Silicon Valley; collaborate with the City Year Headquarters People Team to ensure that City Year San José/ Silicon Valley is consistent with policies, procedures, and benefits of City Year, Inc.

  • Develop agenda for and facilitate site leadership meetings and provide tactical & strategic support for quarterly retreats.

  • Foster productive and collaborative relationships internally and externally on behalf of the Executive Director.

  • Monitor all of City Year San José/Silicon Valley’s operating goals by working with department leadership to provide internal and external reporting;  ensure the Executive Director is aware of recommended actions and ensure response interventions are executed.

  • Collaborate with Executive Director and site leadership to manage the implementation, review, and modification of City Year San José/Silicon Valley’s strategic plans. Ensure departmental and site-wide progress is met and remains aligned with staff capacity, financial resources, and stakeholder support.

  • Partner with the Executive Director to manage strategic relationships with key stakeholders (e.g. public officials, school and district partners, business leaders, etc.) and/or key initiatives (e.g. Site Advancement Plans, etc.).

  • Facilitate interdepartmental collaboration by coordinating committees / working groups.

  • Maintain a calendar of relevant events, processes and deadlines to build collaboration and inter-departmental community; create & disseminate announcements, resources, and reminders for the team


Budget Development and Financial Monitoring

  • Monitor site’s financial progress and ensure all departments are forecasting how they will finish in the black at least every other month.

  • Analyze financial statements and revenue projections and prepare reports for ED and Board Finance Committee.

  • Lead annual budget development process in consultation with the Executive Director and site leadership.

  • Collaborate with Executive Director, site leadership and HQ Finance to identify cost savings and revenue generation opportunities, prepare program budgets, and align operating budgets with strategy and donor intent.

  • Provide training and support to department finance leaders.


Board Management 

  • Assist committees with special projects by conducting research, collecting and analyzing data, drafting reports, and preparing presentations for internal and external stakeholders.

  • Serve as staff liaison in supporting the board, development team and other staff board relationship managers to increase communication and efficiency.

  • With direction from the Executive Director and in conjunction with the Special Projects and Government Relations Manager, manage meetings and materials, retreats, and communications of the Advisory Board.

  • Serve as staff liaison to the Nominations & Governance Committee and Corps Member Experience Committee.


Site Strategy, Improvement, and Strategic Initiatives 

  • Work with staff across the departments to identify obstacles, assess data, and coach them through analysis for improvement.

  • Develop new analytics in collaboration with input from stakeholders to organization wide deployment.

  • Assist budget forecasting with data analysis and predictive analytics

  • Support creation of analysis of program impact drivers, from data selection, to prototype for improving our service model

  • Complete Executive projects. Support the initiatives and responsibilities of the ED by completing special projects throughout the year, as identified, and requested by the ED.

  • Collaborate with Executive Director and site leadership to manage the implementation, review, and modification of City Year San José/Silicon Valley’s strategic plans. Ensure departmental and site-wide progress is met and remains aligned with staff capacity, financial resources, and stakeholder support.


People & Operations

  • Lead the site’s work on Diversity, Belonging, Inclusion, and Equity (DBIE) strategies including the DBIE Council, developing and implementing a DBIE strategic plan; provide guidance on initiatives including learning opportunities and affinity groups.

  • Create and implement the site’s employee engagement plan, including surveys.

  • Inform and educate staff members on organizational resources, benefits, policies, employment opportunities, and the site’s emergency contingency plan.

  • Serve as a resource to staff and AmeriCorps members with workplace related questions, comments, and / or concerns.

  • Lead the talent acquisition process for staff positions including sourcing talent, recruiting, hiring, onboarding, orientation, and training.



  • 5+ years of experience in a leadership role for a non-profit or service organization.

  • 3+ years experience managing individuals and teams.

  • Operations, HR. and/or complex project management experience strongly preferred.

  • Excellent written and verbal communication skills with a demonstrated ability to build and sustain a range of diverse relationships.

  • Understanding of and respect for the role of Executive Director.

  • Strategic thinker and tactician with executive-level decision making ability.

  • Experience creating and analyzing metrics to improve processes, objectives, and outcomes.

  • Experience managing and developing leaders and leadership teams.

  • Experience drafting, managing, and monitoring budgets, strategic plans, and organizational policies & processes.

  • Detail oriented with a strong grasp of organizational vision and the ability to leverage both to achieve desired results.

  • Skilled delegator with ability to motivate and inspire others.

  • Track record of modeling and creating a professional work environment that supports people and processes to work collaboratively to meet organizational goals.


Compensation and Benefits

This is an onsite position. Full time employees are entitled to compensation commensurate with experience. The range for this position is $_______ to $________. Benefits for full time employees include health insurance with Flexible Spending Account, paid vacation, holidays, parental leave, 401K, and more.


To Apply

Interested qualified applicants should submit a cover letter & resume to:

City Year is committed to a diverse workforce. Individuals from all backgrounds are encouraged to apply.

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