Executive assistant

Simply Business is a digital insurance brokerage that specializes in one thing: protecting the businesses our customers are working hard to build. We’re doing this by simplifying the insurance-buying process for all small businesses, blending together a combination of technology, data, and insurance knowledge. Our proprietary technology platform allows small business owners to easily search and compare quotes from over 20 top-rated insurance providers, customize their coverage, and purchase and access their policies - all online.

Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. Simply Business is passionate about building an outstanding product for our customers - one that empowers their entrepreneurial spirits.

More importantly, we’re doing it all while taking care of our people. We’ve consistently been named a best place to work, including most recently ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100), and Best Places to Work in Boston.

We want team members who have the drive to challenge boundaries. If you’re smart and passionate about delivering brilliant customer experiences, we’d love to hear from you.

*****This is a 6-month contract position*****

As an Executive Assistant you will:

• 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; resolving any issues and suggesting better ways of working to find efficiencies
• Provide high quality administrative support and act as a gatekeeper to ensure the right priorities are kept at the top
• Email and inbox management
• Planning team offsites and luncheons – sourcing new innovative venues
• Arrange travel, visas, hotels, restaurants, cars and create detailed travel itineraries
• Various administrative support: managing expenses, raising POs/invoices, booking couriers, ordering catering for meetings, greeting guests, etc.
• Liaising with internal/external customers and suppliers
• Complete ad hoc projects as assigned and conducting research

What we are looking for:

• 8 years experience working as an Executive Assistant (min 2 years supporting C Suite)
• Able to work well under pressure and under tight deadlines and able to decipher priorities and make judgement calls when needed
• Strong with coordination, organization skills, as well as time management skills
• Excellent with their IT skills - G Suite
• Exceptional written and oral communication - able to interact with people of all levels in a confident, professional manner
• High on integrity (experienced in handling confidential information and understand the importance of maintaining it), honesty and reliability
• Knowledgeable of Boston restaurants and social venues is a plus
• Positive and outgoing in their personality and is a team player

Here are some of the great benefits and perks that come from being a Simply Business employee:

• Group plan for medical, dental, vision, and prescription drug coverage
• Short term disability, long term disability, and life insurance coverage
• Participation in the Company’s bonus program-Participation in 401(k) plan with a 5% employer match
• Commuter benefits to help cut down on parking and public transit costs
• 25 days of vacation time plus 10 sick days and 10 company holidays
• A genuine investment in your learning and development-Regular team outings and volunteer opportunities
• An awesome office space
• A hybrid working model, giving our employees great choice and flexibility to work in a way that’s best for their particular job, their teams, and their lives.

Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture. And that commitment starts with our interview process.

Once you apply, your info will be reviewed by a team with a mix of levels and experiences. We pride ourselves on fostering a sense of community, which is only made stronger by each individual at SB, so you’ll have the opportunity to meet a variety of people throughout the process. Get excited!

Most of our first round interviews will take place over Zoom. In subsequent interviews, there may be an opportunity/expectation to meet team members in person.

If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom first regardless – you’ll need WiFi and a laptop, or a 4G-enabled smartphone. If you don’t have access to either of these, or you need support with your application, get in touch with us at [email protected].

Please email us with any questions or if you want to pause your application for a bit – we’ll be happy to keep you updated on future opportunities like the one above. Want more info on working at Simply Business? Check out our careers page: simplybusiness.com/careers/