Chief of Staff

Orlando, FL
Remote ✅
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Apply before: 
Sep 16, 2023

Job title

Chief of Staff

Reports to

Chief Executive Officer

About Us

Founded in April 2011, 26Health (formerly known as Two Spirit Services, Inc.) is a non-profit, 501c3 corporation providing mental health, behavioral, substance abuse, primary medical care, family practice medicine, transgender health and related services to individuals in the LGBT community. We pride ourselves on having a diverse staff that promotes optimum health and wellness. We provide a broad variety of integrated and culturally competent services for the Mind, Body and Spirit, regardless of insurance. We focus on the LGBTQ+ and Ally community, including all members of the sexual orientation and gender identity spectrum.

Job purpose

The Chief of Staff (CoS) serves as Board Liaison and is the point of collaboration between the Chief Executive Officer (CEO) and the Board of Directors (Board). They will serve as the vital point of contact for the Board and support the CEO, Board, and the Board committees as a strategic thinker and project manager. The primary purpose of the CoS is to provide vital strategic coordination and administrative support to the CEO and the Executive Leadership Team.

Sitting within the Executive Office attends to sensitive matters, decision-making processes, and documentation of outcomes in support of activities, fostering collaborative workflow and teamwork within the Executive Office. The role has a strategic focus and regularly exercises considerable discretion and independent judgment in performing duties.

The CoS will is expected, on a daily basis, to remain in regular contact with the CEO and the Executive Leadership Team, keeping them informed of all matters requiring review, approval, guidance, and intervention.

Duties And Responsibilities

  • Oversee planning, preparation, implementation, and follow-up for business meetings. In partnership with the CEO and Board Chair, develop board/committee meeting schedule, agenda and provides background materials for board deliberations. Confer with necessary stakeholders as needed to establish board meeting updates and reports.
  • Oversee all planning and logistics around board support, including regular meetings, committee meetings, and correspondence.
  • Plan and direct the board affairs administrative functions and daily operations, Support in developing the board affairs annual budget, and management oversight and administration of the budget.
  • With support from the Executive Assistant, assemble all Board documents for the CEO and ensure all requisite materials are ready in preparation for meetings (e.g., talking points, etc.)
  • Ensures the timely preparation, publishing, and distribution of materials (e.g., requests, agenda, schedules, notices, resolutions, etc.) for the ELC committee meetings, utilizing diligence and coordinating with other departments to provide approved content, reports, and update.
  • Project manage the creation of policies, procedures, and documents, which various members of the organization's leadership team in an iterative process draft.
  • In close collaboration with the CEO, review all documents before finalizing and serve as a final copyeditor.
  • With support from the Executive Assistant and in collaboration with the relevant teams as necessary, ensure all meetings, retreats, and fundraising events that implicate the organization are scheduled, calendared, and shared with the CEO and Board of Directors well in advance.
  • Participate in weekly transition team meetings, document plan updates in the project management system, create and follow up on action items, and manage due dates.

Board and Strategic Plan Support

  • Helps the CEO to stay aligned with the strategic plan and to be proactive in assisting them in meeting and monitoring the set goals.
  • Participates in and supports strategic thinking, planning, and leadership.
  • Responsible for special project management and support as directed by the CEO and the Board Chair.
  • Manage all aspects of Board-level committees, preparing agendas in partnership with various Committee Chairs, assembling and disseminating preparatory materials
  • Support the Board Secretary when required to attend Board meetings to capture the next steps and official minutes,
  • Work with committee chairs and Board members as needed to track action items and accomplish committee-related tasks.
  • Working to ensure the daily calendar, briefing, and support materials for the CEO are managed and maintained to optimize their vision setting, strategic thinking, and innovation.
  • Operate with a clear understanding of the breadth of projects and the priorities under the CEO’s purview.
  • Manage the correspondence between the CEO, Board, and other parties, including ELT and staff.
  • Liaise with Community Impact, Communications, and Public Relations to ensure the CEO is effectively aware and up to date on community engagement events, media communication calendars, and requests for interviews and representation, both written and in-person.
  • Draft internal memos on behalf of the CEO and prepares external meeting reports.
  • Creates, organizes, and maintains accurate electronic files and hardcopy folders.
  • Manages special projects for the CEO
  • Prioritizes conflicting needs; handles matters expeditiously and proactively follows through on projects to successful completion, often with deadline pressures.
  • Supports the Executive Office in strategic collaborations with other departments,
  • Builds and maintains relationships with and information flow to external advisors and key stakeholders.
  • Tracks and collect data for the Interim CEO's weekly transition team report and organizational assessment.
  • Demonstrates excellent follow-through on tasks and projects to ensure successful completion, often with short deadlines
  • Communicate regularly with the CEO, ELT, and administrative team to ensure that they are kept informed and up to date.
  • Coordinate submission of Monthly Board updates and dissemination of relevant Committee reports.
  • Serve as the point of contact for the CEO and Board for all things, both logistical and tactical.
  • Maintain Board email groups and up-to-date contact information.
  • Support the CEO in setting agendas for board engagements and project manage members of the Executive Leadership Team in creating material and content.
  • Actively contributes to organizing a diverse and equitable workplace through inclusive practice and openness to different perspectives, cultures, and ideas.


  • Bachelor’s degree (or equivalent experience) in business administration or public health
  • Experience in organizing and directing multiple teams and departments

Working conditions

Prolonged periods sitting at a desk and working on a computer.

Physical Requirements

There are no extreme physical requirements for this position.

Direct reports


Additional Information

Background screens will be performed and education will be verified prior to employment. Please be prepared to provide required information and/or documentation.

26Health is a smoke-free workplace, and smoking is prohibited in all enclosed areas of the property.

26Health is an equal opportunity, affirmative action employer.


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