Executive Assistant to the Chief of People & Culture and the VP of People & Culture.

PINE STREET INN INC•Boston, MA

7h•$68,000 - $80,000•Hybrid

About The Position

The Executive Assistant provides high-level administrative and operational support to the Chief of People & Culture and the VP of People & Culture. Reporting to the Chief of People & Culture, the position supports consistent, coordinated executive operations, including leadership meetings, company events, expense reporting, and compliance. The successful candidate is organized, resourceful, discreet, and able to balance the needs of multiple executives as schedules and priorities change. The schedule is 40 hours per week, Monday through Friday, 8:30 a.m. to 5:00 p.m. The role follows Pine Street Inn’s hybrid working model, with on-site work three days per week and remote work two days per week. It also participates in the HR Department’s Friday rotation, typically about one Friday every five to six weeks. The position is located at 434 Harrison Ave, Boston, Massachusetts. The listed annual pay range is $68,000–$80,000, depending on experience and relevant skill set. Pine Street Inn is New England’s largest provider of services to individuals experiencing homelessness. Founded in 1969, it serves more than 2,000 people each day through emergency shelter, permanent supportive housing, street outreach, and employment and workforce development programs. Its mission is to provide a compassionate and safe environment and essential services while supporting people’s movement toward self-sufficiency and more stable lives. The organization also views technology as a strategic lever to advance its mission, improve service delivery and operational efficiency, and enable data-driven decision-making. The Executive Assistant provides comprehensive support to both executives, managing complex calendars, preparing communications and materials, submitting expense reports, tracking priorities and follow-ups, and handling confidential information. The role also plans executive meetings and organizational events, coordinating logistics, vendors, budgets, materials, and follow-up. Additional duties include serving as a professional point of contact, supporting communications and relationships, assisting with special projects, maintaining administrative resources, improving processes, and providing backup support to other administrative professionals as needed.

Requirements

Associate or bachelor’s degree preferred, or an equivalent combination of education and relevant experience.
At least five years of progressively responsible administrative experience, including direct support of senior executives.
Experience supporting multiple executives with competing priorities.
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.
Ability to exercise independent judgment, solve problems, and maintain confidentiality.
Ability to work effectively with limited supervision and adapt quickly to changing business needs.

Responsibilities

Provide comprehensive administrative support to the Chief of People & Culture and the VP of People & Culture.
Manage complex and frequently changing calendars, including meetings, appointments, travel, and competing priorities.
Identify scheduling conflicts, recommend solutions, and prepare executives for upcoming commitments.
Draft, review, and format correspondence, presentations, meeting materials, reports, and executive communications.
Prepare and submit accurate, timely expense reports in accordance with company policies.
Track executive priorities, commitments, deadlines, and follow-up items.
Handle confidential and sensitive information discreetly and in accordance with the organization’s confidentiality policy.
Plan and coordinate executive meetings, leadership conferences, town halls, off-site meetings, and company events.
Coordinate event logistics, including venues, contracts, accommodations, transportation, catering, audiovisual needs, room setup, agendas, and attendee communications.
Work with internal teams and external vendors to deliver events professionally, on time, and within budget.
Prepare agendas, presentations, pre-read materials, attendee lists, and other meeting resources.
Attend or support events as needed, oversee logistics, troubleshoot issues, and support 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.
Serve as a professional point of contact between executives and employees, customers, and vendors.
Manage incoming requests and communications, prioritizing, responding, redirecting, or escalating matters appropriately.
Build working relationships across functions, business units, and organizational levels.
Provide backup support to other administrative professionals as needed.
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.