Office Manager/Executive Assistant

The Office Manager & Executive Assistant to Partners is a key member of the team responsible for ensuring the office runs smoothly day-to-day while providing high‑quality administrative support to firm Partners. This role also partners closely with People & Culture on events, employee experience initiatives, and coordinating early-stage recruiting activities (including scheduling interviews for entry-level and support roles).
The ideal candidate is proactive, highly organized, detail‑oriented, and comfortable juggling multiple priorities in a fast‑paced, professional environment.
What you'll bring to Sentinel:

• Organization & Prioritization: Able to manage multiple tasks, deadlines, and stakeholders with strong follow‑through.
• Professional Communication: Clear, polished written and verbal communication; represents the firm and Partners professionally with all audiences.
• Discretion & Integrity: Handles confidential and sensitive information with the highest level of professionalism.
• Service Orientation: Proactive, responsive, and focused on creating a positive experience for employees, Partners, candidates, and visitors.
• Problem Solving: Resourceful, with the ability to anticipate needs, identify issues, and propose practical solutions.
• Collaboration: Works effectively with People & Culture, Operations, IT, and other teams to support a cohesive office and employee experience.

What you’ll be responsible for:

• Oversee the day-to-day operations of the office, ensuring a professional, organized, and welcoming environment.
• Monitor and order office supplies, snacks, and equipment, maintaining appropriate inventory levels.
• Lead office logistics for in-person meetings, trainings, and firm gatherings (room setup, AV support coordination, catering, materials).
• Maintain reception or front-desk coverage standards (whether personally or via vendors), including greeting guests and ensuring sign-in/security protocols are followed.
• Answers and transfers internal or external phone calls on ak multi-line phone and relays messages.

• Partner with HR/People & Culture to plan and execute employee events (appreciation events, holiday parties, culture & belonging activities).
• Help coordinate event logistics including catering, room/space setup, materials, and day‑of support.
• Partner with P&C to schedule “low-level” or early-stage interviews, including entry‑level, support, and administrative roles.
• Coordinate candidate communications (confirmations, directions, virtual meeting links, rescheduling, thank‑you notes as requested).
• Arrange interview schedules across multiple interviewers, managing calendar holds and changes efficiently.
• Ensure candidates have a positive and professional experience, whether on-site or virtual (greeting in reception, escorting to conference rooms, etc.).

• Provide high‑touch administrative and scheduling support to assigned Partners.
• Manage calendars, including internal/external meetings, travel time, and recurring commitments
• Coordinate travel, including flights, hotels, ground transportation, and itineraries.
• Prepare and process expense reports, reimbursements, and related documentation accurately and on time.
• Assist with meeting preparation, including agendas, materials, presentations, and follow‑up actions as requested.

• Perform clerical duties, such as data entry
• Collects and distributes mail.
• Scanning of documents and mail to different departments.
• Processing and scanning checks into check tracking system
• Scanning and processing Enrollment and Claims Forms into Laserfiche system
• Provide backup administrative support to other leaders or teams during peak periods or absences.
• Support special projects as assigned by Partners or HR/People & Culture (e.g., office improvements, process updates, policy rollouts)

• Receives outgoing mail and applies correct postage or prepares for special delivery
• May have to go to Post Office with bins of outgoing mail when necessary
• Operates mail machines including the postage meter, photocopying machine, and mail folding and inserting machine.
• Assists in printing, collating and binding reports.
• Monitors machine operation and makes adjustments as necessary to ensure proper operation.
• Maintains records of receipt, mailing dates, and other required information as needed.
• Replenishes postage on the postage meter as needed.
• Stocks supplies needed for the mailroom.
• Performs other related duties as assigned.

About you: 
We’re looking for a proactive, highly organized Office Manager who takes pride in creating a smooth, welcoming, and efficient workplace. You’re comfortable balancing structure with flexibility in a fast-paced environment and are energized by supporting people so they can do their best work while continually improving how our offices run.
What you need to have:
Preferred qualifications:

• 3–5 years of experience in an office manager, administrative, or operations support role
• Proven track record of owning day-to-day office operations and keeping things running smoothly
• Strong organizational and time management skills; able to prioritize and juggle multiple requests
• Exceptional attention to detail with a focus on accuracy in scheduling, documentation, and recordkeeping
• Confident, professional communication skills (verbal and written) across all levels of the organization
• Demonstrated ability to provide approachable, high-touch support to employees and visitors
• Strong problem-solving skills with a “find a way” mindset when unexpected issues arise
• Collaborative, team-oriented approach with a willingness to jump in wherever needed
• Salary Range:  $48,000-$54,000

At Sentinel, compensation is calibrated to your geographic location to reflect local market conditions; the posted salary range may vary based on where you live.
What you’ll be part of:
Joining our company means becoming part of something special. We're driven by a mission to excel in our industry and within our team, supported by people who truly care about our organization.
Sentinel was recently recognized by The Boston Globe as a Top Place to Work in 2020 and 2023. In 2021, 2022, 2023 and 2024, Sentinel earned a Top Workplace USA Award from Energage.
At Sentinel, we welcome people from diverse experiences, backgrounds, and perspectives – and we wouldn’t have it any other way. So even if you don’t meet every single requirement, please consider applying if you like what you see. Our priority is to find talented individuals who enrich our team culture, contribute with enthusiasm, and are passionate about what they do.
Sentinel is an equal opportunity employer and welcomes everyone to our team. If you need reasonable adjustments at any point in the application or interview process, please let us know
Some of our Benefits:

• PTO (vacation, sick, personal time bank)
• FTO (Flexible time off for vacation, sick, and personal time) after 2 years of service
• 12 Paid Holidays (10 stated and 2 floating holidays)
• 2 Community Volunteer Days
• 5 Summer Half Days
• Medical, Dental, Vision
• Life Insurance
• LTD & STD
• Retirement Plan with 4% Employer Match
• Parental Leave

See What We Stand For: https://www.sentinelgroup.com/About-Us/Join-Our-Team
Who we are:
Sentinel Group proudly serves nearly 5,000 clients throughout the U.S. For 35+ years, we’ve remained devoted to positively impacting the lives of our people, our clients and our communities. With a 9-year average associate tenure among our 265 professionals, our team’s commitment to excellent service has positioned Sentinel as the only provider who makes benefits EASY: easy for your people; easy for your business; and easy for you.
Our ultimate goal is to help companies and their employees prepare for their future health, wealth and retirement needs. Whether it’s through retirement plans, group health insurance, reimbursement accounts or financial planning, we engineer simple solutions and continuously strive to make them better. Our in-house experts – and their commitment to excellence – define who we are.
Sentinel is also one of the largest employee benefits firms in Massachusetts (Boston Business Journal) and was named a 2022 Retirement Plan Adviser of the Year in the Mentorship category (PLANADVISER Magazine).