Executive Assistant to the CEO

Who We Are Bridge Over Troubled Waters (Bridge) is Boston's foremost agency providing age-appropriate services for homeless, runaway, and at-risk youth. Nowhere else in Boston can young adults take classes towards their GED, find a job with the assistance of a workforce developer, consult a professional counselor, or enter a cooperative apartment – all under the same roof. For over 50 years, Bridge has provided effective and innovative services to help youth avoid a lifetime of dependency on social services, guide youth towards self-sufficiency, and enable youth to transform their lives and build fulfilling, meaningful futures.

What You’ll Do The Executive Assistant will provide exceptional support to Bridge’s CEO, Elisabeth Jackson. This role manages the CEO’s time and priorities, operates with the utmost discretion and professionalism, liaises with the board of directors, and supports overall office operations. Specifically, the Executive Assistant will:

Oversee executive workflow, communications, and board coordination

• Own and prioritize the CEO’s calendar, balancing competing requests, protecting focus time, and preventing scheduling conflicts.
• Act as a trusted gatekeeper, triaging requests and responding or following up on behalf of the CEO using sound judgment.
• Prepare the CEO for meetings by ensuring materials, context, and logistics are handled in advance.
• Draft and send professional correspondence including follow-ups, acknowledgements, and routine communications.
• Coordinate travel planning several times per year, including itineraries and reservations.
• Lead all logistics for the Board of Directors (4 meetings annually), including setting timelines, collecting reports, compiling the board book, managing review and distribution, and coordinating meeting logistics.
• Manage incoming board communication and route requests appropriately to protect staff time.
• Track action items and ensure follow-through across leadership and board interactions.

Support the smooth and efficient execution of office operations

• Help the organization run smoothly day-to-day while enabling senior leaders to stay focused on program and strategy.
• Supervise and coordinate office support staff and administrative functions.
• Manage meeting logistics, lunches, reservations, and internal coordination for leadership meetings.
• Support senior leadership team members with scheduling and special projects as needed.
• Partner with finance team on expenses, reimbursements, and related documentation.
• Maintain organized records and operational systems for meetings and board materials.
• Anticipate operational gaps and resolve them independently before they escalate.

You May Be The Right Candidate If You Are

• A seasoned Executive Assistant who manages priorities, not just tasks. You bring 5+ years supporting a senior leader and understand how to keep work moving in a high-demand environment.
• A trusted professional with sound judgment. You handle confidential information with discretion and make appropriate decisions independently, knowing when escalation is needed.
• A proactive manager-up who anticipates needs. You close loops, follow through, and advance work without waiting for direction.
• An exceptionally organized operator who maintains clarity across moving pieces. You track details across calendars, meetings, and stakeholders without dropping threads.
• A polished communicator who represents leadership well. You draft clear, professional correspondence and interact comfortably with board members, donors, and staff.
• A low-ego, dependable contributor who values consistency. You require minimal oversight and take pride in keeping operations running smoothly behind the scenes.
• An effective steward of leadership time and relationships. You navigate dynamics thoughtfully and ensure requests reach the right people at the right moment.

TOOLS AND KEY RELATIONSHIPS

• Outlook, Teams, Zoom, Excel, and scheduling tools (e.g., Doodle Poll).
• This role works closely with finance, development, and program leadership and supervises administrative support staff.

Salary And Benefits The salary for this position is in the range of $75,000 - $100,000 depending on depth and breadth of experience as an Executive Assistant. Benefits include:

• Paid time off (sick time, vacation time, personal time) as well as 13 paid holidays and a birthday holiday
• Health, dental, and vision insurance
• 401(K) with 3% matching of contributions after 90 days of employment
• Employer sponsored flexible spending accounts, commuter pre-tax benefits, employer paid short-term disability, long term disability and life insurance

TO APPLY Please apply with your 1) a thoughtful cover letter that conveys why this opportunity is of interest and 2) your resume. Please address your cover letter to Elisabeth Jackson, Chief Executive Officer. We review applications on a rolling basis and strive to get back to applicants within two weeks.

Bridge Over Troubled Waters has retained DH Search to support the hiring of an Executive Assistant. DH Search is a national search firm that works exclusively with nonprofits and mission-driven organizations to recruit and hire extraordinary people. Learn more at www.dhsearch.net