SCHEDULE: 40 hours per week, Monday thru Friday 8:30am – 5pm. The role operates in PSIs hybrid working model with on-site requirements 3x/week and 2 days remote. Additionally, the role requires participation in the HR Department’s Friday rotation (usually about 1 Friday every 5-6 weeks.  

Pay: $68,000 - $80,000 annually DOE (salary ranges are based on experience and relevant skill set)

Location:434 Harrison Ave, Boston MA

About Pine Street Inn

Pine Street Inn is New England’s largest provider of services to individuals experiencing homelessness. Founded in 1969, we serve more than 2,000 people each day through emergency shelter, permanent supportive housing, street outreach, and employment and workforce development programs. Our mission is to provide a compassionate and safe environment, as well as essential services, to homeless individuals while supporting each person’s movement toward self-sufficiency and more stable lives.

Pine Street Inn is committed to using technology as a strategic lever in advancing our mission — improving service delivery, strengthening operational efficiency, and enabling data-driven decision-making across all of our programs.

Position Overview:

The Executive Assistant provides high-level administrative and operational support to two executive-level leaders within the Human Resources Department. Reporting to the Chief of People & Culture, this position will help ensure consistent, coordinated, and high-quality executive support while assisting with leadership meetings, company events, expense reporting, and compliance.
 

The ideal candidate is highly organized, resourceful, discreet, and comfortable balancing the needs of multiple executives whose schedules and priorities may change frequently. Success requires strong judgment, attention to detail, professionalism, and the ability to anticipate needs in a fast-paced, evolving environment.
 

Essential Functions & Responsibilities
 

Executive Support

• Provide comprehensive administrative support to both the Chief of People & Culture and the VP of People & Culture. 
• Manage complex and frequently changing calendars, including meetings, appointments, travel, and competing priorities. 
• Proactively identify scheduling conflicts, recommend solutions, and ensure executives are prepared for upcoming commitments. 
• Draft, review, and format correspondence, presentations, meeting materials, reports, and executive communications. 
• Prepare and submit timely and accurate expense reports in accordance with company policies. 
• Track executive priorities, commitments, deadlines, and follow-up items to support accountability and timely execution. 
• Handle confidential and sensitive information with the highest degree of discretion and professionalism while adhering to PSIs confidentiality policy.
   

Meeting and Event Planning

• Plan and coordinate executive meetings, leadership conferences, town halls, off-site meetings, and company events. 
• Manage event logistics, including venue selection, contracts, accommodations, transportation, catering, audiovisual needs, room setup, agendas, and attendee communications. 
• Partner with internal teams and external vendors to ensure events are delivered professionally, on time, and within budget. 
• Prepare agendas, presentations, pre-read materials, attendee lists, and other meeting resources. 
• Attend or support events as needed to oversee logistics, troubleshoot issues, and ensure a positive attendee experience. 
• Capture key decisions and action items and coordinate follow-up after meetings and events. 
• Track event budgets, invoices, contracts, and vendor commitments.  
   

Communication and Relationship Management

• Serve as a professional point of contact between executives and employees, customers, vendors.
• Manage incoming requests and communications, using sound judgment to prioritize, respond, redirect, or escalate matters appropriately. 
• Build strong working relationships across functions, business units, and levels of the organization. 
• Provide backup support to other administrative professionals as needed.  
   

Operational and Project Support

• Assist with special projects, research, data gathering, presentations, and other business initiatives. 
• Develop and maintain administrative processes, files, contact lists, organizational materials, and shared resources. 
• Identify opportunities to improve efficiency, communication, and coordination across the executives and teams supported. 
• Help establish and maintain consistent executive support practices across the organization.

 Qualifications & Experience

• Associate or bachelor’s degree preferred, or an equivalent combination of education and relevant experience. 
• Minimum of five years of progressively responsible administrative experience, including direct support of senior executives. 
• Demonstrated experience supporting multiple executives with competing priorities. 
• Demonstrated experience planning executive meetings, conferences, off-site sessions, or company events. 
• Advanced proficiency in Microsoft Outlook, Word, PowerPoint, Excel, and Teams. 
• Strong written and verbal communication skills. 
• Exceptional organization, time management, and attention to detail. 
• Demonstrated ability to exercise independent judgment, solve problems, and maintain confidentiality. 
• Ability to work effectively with limited supervision and adapt quickly to changing business needs.