Simply Business
Overview
Simply Business is a digital insurance brokerage that specializes in protecting the businesses our customers are building. We simplify the insurance-buying process for small businesses by blending technology, data, and insurance expertise. Our proprietary technology 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 supporting small businesses. We are committed to building outstanding products and taking good care of our people. We are recognized as a great place to work, including ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100) and Best Places to Work in Boston. We seek team members who are driven to challenge boundaries and deliver brilliant customer experiences. This is a 6-month contract position. Responsibilities
Provide first-class day-to-day executive assistant support to the executive team: US CEO, Global Chief People Officer, and Global Chief Technology Officer; act as a main point of contact and gatekeeper for calendars and availability Organize and manage complex calendars and schedules; resolve issues and suggest efficient ways of working Provide high-quality administrative support and act as a gatekeeper to keep priorities at the top Email and inbox management Plan team offsites and luncheons, sourcing new innovative venues Arrange travel, visas, hotels, restaurants, cars, and create detailed travel itineraries Handle various administrative tasks including expenses, PO/invoices, couriers, catering for meetings, and greeting guests Liaise with internal/external customers and suppliers Complete ad hoc projects as assigned and conduct research What we are looking for
8 years of experience as an Executive Assistant (minimum 2 years supporting C‑Suite) Ability to work well under pressure with tight deadlines; strong prioritization and judgment Strong coordination, organizational, and time-management skills Proficiency with IT tools, especially G Suite Excellent written and verbal communication; professional interaction with all levels High integrity with experience handling confidential information Knowledge of Boston restaurants and social venues is a plus Positive, outgoing, and a team player Benefits
Group medical, dental, vision, and prescription drug coverage Short-term and long-term disability and life insurance Participation in the company bonus program and 401(k) with 5% employer match Commuter benefits to reduce parking and transit costs 25 days of vacation, 10 sick days, and 10 company holidays Investment in learning and development; regular team outings and volunteer opportunities Modern office space Hybrid working model for flexibility across roles Simply Business is an equal opportunity employer. We are committed to an inclusive and diverse culture and to fostering growth within our interview process. If you apply, your information will be reviewed by a team with varied levels and experiences. We value a sense of community at SB and you’ll have the opportunity to meet a variety of people during the process. Most first-round interviews are conducted via Zoom, with possible in-person meetings in later rounds. If you could be a good fit, we’ll ask you to interview on Zoom first; you’ll need WiFi and a laptop or a 4G-enabled smartphone. If you need support with your application, contact us at uscareers@simplybusiness.com.
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Simply Business is a digital insurance brokerage that specializes in protecting the businesses our customers are building. We simplify the insurance-buying process for small businesses by blending technology, data, and insurance expertise. Our proprietary technology 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 supporting small businesses. We are committed to building outstanding products and taking good care of our people. We are recognized as a great place to work, including ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100) and Best Places to Work in Boston. We seek team members who are driven to challenge boundaries and deliver brilliant customer experiences. This is a 6-month contract position. Responsibilities
Provide first-class day-to-day executive assistant support to the executive team: US CEO, Global Chief People Officer, and Global Chief Technology Officer; act as a main point of contact and gatekeeper for calendars and availability Organize and manage complex calendars and schedules; resolve issues and suggest efficient ways of working Provide high-quality administrative support and act as a gatekeeper to keep priorities at the top Email and inbox management Plan team offsites and luncheons, sourcing new innovative venues Arrange travel, visas, hotels, restaurants, cars, and create detailed travel itineraries Handle various administrative tasks including expenses, PO/invoices, couriers, catering for meetings, and greeting guests Liaise with internal/external customers and suppliers Complete ad hoc projects as assigned and conduct research What we are looking for
8 years of experience as an Executive Assistant (minimum 2 years supporting C‑Suite) Ability to work well under pressure with tight deadlines; strong prioritization and judgment Strong coordination, organizational, and time-management skills Proficiency with IT tools, especially G Suite Excellent written and verbal communication; professional interaction with all levels High integrity with experience handling confidential information Knowledge of Boston restaurants and social venues is a plus Positive, outgoing, and a team player Benefits
Group medical, dental, vision, and prescription drug coverage Short-term and long-term disability and life insurance Participation in the company bonus program and 401(k) with 5% employer match Commuter benefits to reduce parking and transit costs 25 days of vacation, 10 sick days, and 10 company holidays Investment in learning and development; regular team outings and volunteer opportunities Modern office space Hybrid working model for flexibility across roles Simply Business is an equal opportunity employer. We are committed to an inclusive and diverse culture and to fostering growth within our interview process. If you apply, your information will be reviewed by a team with varied levels and experiences. We value a sense of community at SB and you’ll have the opportunity to meet a variety of people during the process. Most first-round interviews are conducted via Zoom, with possible in-person meetings in later rounds. If you could be a good fit, we’ll ask you to interview on Zoom first; you’ll need WiFi and a laptop or a 4G-enabled smartphone. If you need support with your application, contact us at uscareers@simplybusiness.com.
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