May 27, 2022

Chief of Staff

$120,000 - $140,000 yearly
  • The Osborne Association
  • Bronx, NY, USA
Full-Time Administration/Operations Diversity, Equity, Inclusion, Belonging Executive Management (CEO/ED)

Job Description

The Osborne Association serves individuals, families, and communities affected by the criminal justice system. Through our programs, we offer opportunities for people to heal from and repair harm, restore their lives, and thrive. We challenge systems rooted in racism and retribution and fight for policies and practices that promote true safety, justice, and liberation.

At Osborne, we are guided by core values and shared beliefs. We honor everyone's capacity to change, celebrate our shared humanity, are united in our pursuit of justice and equity, take all possible steps to keep our commitments, and advocate for people and principles with fierce and tenacious determination.

Osborne is seeking a Chief of Staff  (COS) to join their dynamic leadership team. The Chief of Staff serves as a thought partner and trusted advisor to Osborne’s President and Chief Executive Officer (CEO) and supports the implementation of the CEO’s strategic priorities, advances transparency, accessibility, inclusion, and a participant-centric focus through internal communications and collaboration, and manages and prioritizes the workflow of the CEO’s office. The COS supports the CEO by fielding and prioritizing incoming requests in concert with strategic priorities, proactively advising on and preparing internal communications, and anticipating and addressing challenges before they arise. They have exceptional communication skills and can build strong relationships to influence, collaborate with, and generate actionable results with staff at all levels of the organization. The COS supports the Executive Team and other key staff in presenting information to the CEO concisely, promptly, and with the right level of detail. They handle complex situations and multiple responsibilities simultaneously, balancing long-term priorities with the urgency of immediate demands. 

The COS will advance the organization's diversity goals and demonstrate and share in the organization’s commitment to anti-racism, equity, and inclusion. They will make decisions, contribute to discussions, and manage conflict through a DEI lens and in concert with Osborne’s core values. 

They are an excellent writer who prioritizes sharing relevant and targeted information with key internal stakeholders. The COS will also handle highly sensitive and confidential information with the utmost discretion and is authorized by the CEO to act in her stead when needed and as appropriate, including representing her in meetings and discussions both internally and externally.


The Chief of Staff position is full-time and has a Monday through Friday 9:00 AM to 5:00 PM hybrid schedule. The schedule is subject to change due to program/ department needs.

The salary range for this position is $120,000- $140,000.


 Staffing the President and CEO

  • Strategize with and advise the Chief Executive Officer on organizational challenges and  opportunities  
  • Manage executive communications, including drafting and coordinating internal and external messages, including emails, quotes, statements, speeches, presentations, and reports.
  • Lead and manage projects across Osborne's functional areas that require interdepartmental collaboration.
  • Participate as a member of the Executive Team and help to direct its work; ensure alignment with the CEO’s priorities and that objectives are met. 
  • Collaborate with the CEO’s Executive Assistant on meeting prioritization, systems, materials, and communication.
  • Coordinate resources and decision-making processes, while ensuring that involvement of the CEO is strategic and occurs at the right time.
  • Identify, stay abreast of, and brief the CEO on high-level emerging or urgent issues and ensure a timely response
  • Facilitate the CEO’s communications with the Osborne Board of Directors and work with the CEO’s Executive Assistant to coordinate Board materials. 
  • In concert with the VP of Development and other internal stakeholders, develop strategies for external stakeholder engagement, including donors, funders, external partners, and relevant colleagues.
  • Proposes the creation of new systems and processes to streamline CEO and Executive Team functioning.

Anti-Racism, Equity, and Inclusion          

  • Understand how institutional racism manifests in social services agencies.
  • Champion anti-racist and anti-oppressive stances.    
  • Strong sense of cultural humility and emotional intelligence.    
  • Ability to supervise, make decisions, and manage conflict with a DEI lens. 
  • Ability to engage in courageous conversations.

Internal Communications

  • Foster a culture of internal communications and listening to advance transparency, inclusion, access, and our participant-centric focus.
  • Develop Osborne’s internal communications and content strategy in partnership with key stakeholders: Human Resources, Communications, Policy, and Programs staff. 
  • Oversee a comprehensive calendar of internal communications and work directly with Communications staff to create and share key messages that are authentic, consistent, and aligned with Osborne’s organizational priorities and values.

Meeting and Event Preparation

  • In collaboration with other senior staff, identify and facilitate internal and external meetings needed to advance the CEO’s priorities.
  • Establish processes to ensure the CEO’s meetings are well organized, relevant, efficient, and produce actionable outcomes. Follow up on action items from all meetings.
  • Ensure the CEO is prepared for all events with briefing materials and, as appropriate, prepared remarks. Work with event planner/facilitator on the run of show and manage all other logistics on behalf of the CEO.
  • Represent the CEO’s voice and interests in event planning meetings.  

The Osborne Association is an EEO/Affirmative Action employer and a VEVRAA Federal Contractor. All qualified applicants will receive consideration for employment and will not be discriminated against based on race, color, religion, sex, sexual orientation, national origin, age, disability, protected veteran status, unemployment status, or any other protected category. The Osborne Association takes affirmative action in support of its policy to advance in the employment of individuals who are minorities, women, protected veterans, and individuals with disabilities.

The agency is an NYC contractor and also provides services to facilities upstate, therefore we adhere to all state and city COVID 19 vaccine mandates. With the exception of an approved exemption/accommodation, effective December 1, 2021, all staff must be fully vaccinated, and provide proof of vaccination.

Thank you for your interest in the Osborne Association. Be sure to include a cover letter with your application. No phone calls, please. We wish we could personally respond to each application. However, we are unable to do so due to the volume of interest received.

Hiring Organization

The Osborne Association




The COS will have a Bachelor’s Degree (Master’s preferred) or a minimum of ten (10) years of senior-level experience in organizational administration, and at least three years of experience in a similar position. The ideal candidate will have the acumen and finesse to handle complex situations and multiple responsibilities, simultaneously mixing long-term projects with the urgency of immediate demands. They must possess exceptional judgment and communication skills, collaborate with and achieve actionable results through others, build strong and sustainable relationships, and interact effectively within all levels of the organization and with external constituents.

Additional Skills: 

  • Commitment to racial, cultural, and socioeconomic equity and justice.
  • Experience with metrics to evaluate organizational performance against goals to facilitate continuous improvement
  • Impeccable communication and interpersonal skills.
  • Strong time management and organizational skills, including the ability to multitask, be flexible, and work well under pressure.
  • Strong project management skills with excellent attention to detail.
  • Knowledge of the criminal justice system is a plus, but a willingness to learn is essential.

Industry/Service Area

Human Services, Other




Benefits of Working at Osborne

Generous benefits include four weeks of vacation, tuition reimbursement, a flexible work schedule, excellent Medical, Dental, and Vision insurance, and a 403(b) plan with a company match. Career development through ongoing training and individual development plans.

Application Instructions

Please click Apply Now to submit your application

Apply Now