Executive Assistant Job at Simply Business in Boston

Executive Assistant at Simply Business (6-month contract)

Simply Business is a digital insurance brokerage that focuses on protecting the businesses our customers are building. We simplify the insurance-buying process for small businesses by combining technology, data, and insurance knowledge. Our proprietary platform lets small business owners search and compare quotes from over 20 providers, customize coverage, and access policies online.

Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience in supporting small businesses. We are committed to building an outstanding product while taking care of our people. We have been recognized as a best place to work, including Built In’s 2025 Best Companies to Work for in the US (Top 100) and Best Places to Work in Boston.

We are looking for team members who are driven to challenge boundaries. If you’re smart and passionate about delivering brilliant customer experiences, we’d love to hear from you.

Responsibilities

• Provide first-class day-to-day EA support to the executive team: US CEO, Global Chief People Officer, and Global Chief Technology Officer, acting as a main point of contact and gatekeeper for calendars and availability
• Organize and manage complex calendars and schedules; resolve issues and suggest new ways of working to find efficiencies
• Provide high-quality administrative support and act as a gatekeeper to ensure priorities are kept at the top
• Email and inbox management
• Plan team offsites and luncheons, sourcing innovative venues
• Arrange travel, visas, hotels, restaurants, cars, and create detailed travel itineraries
• Handle various administrative tasks: expenses, POs/invoices, couriers, catering for meetings, greeting guests, etc.
• Liaise with internal/external customers and suppliers
• Complete ad hoc projects as assigned and conduct research

What we are looking for

• 8 years experience as an Executive Assistant (min 2 years supporting C-suite)
• Ability to work under pressure with tight deadlines, prioritize, and make sound judgments
• Strong coordination, organization, and time management skills
• Excellent IT skills with G Suite
• Exceptional written and oral communication, professional interaction at all levels
• High integrity, discretion with confidential information, honesty, and reliability
• Knowledge of Boston restaurants and social venues is a plus
• Positive, outgoing personality and team player

Benefits

• Group medical, dental, vision, and prescription coverage
• Short-term and long-term disability, and life insurance
• Participation in bonus program and 401(k) with 5% employer match
• Commuter benefits to offset parking and transit costs
• 25 days of vacation, 10 sick days, and 10 company holidays
• Learning and development opportunities; regular team outings and volunteering
• Hybrid working model for flexibility

Simply Business is an equal opportunity employer. We are committed to an inclusive and diverse culture, starting with our interview process.

If you are interested, your information will be reviewed by a diverse team. You’ll have opportunities to meet a variety of people during the process. Most first-round interviews are via Zoom with potential in-person follow-ups.

If you fit the role, we’ll start with a Zoom interview. You’ll need WiFi and a laptop or a 4G-enabled smartphone. If you don’t have access to these, or need application support, contact us at uscareers@simplybusiness.com. For questions or to pause your application, email us and check our careers page: simplybusiness.com/careers/

Boston, MA – compensation will be shared during the interview process.