Simply Business reviews

3.6

60% would recommend to a friend

(305 total reviews)
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David Summers

78% approve of CEO

59% positive business outlook

Simply Business has an employee rating of 3.6 out of 5 stars, based on 305 company reviews on Glassdoor which indicates that most employees have a good working experience there. The Simply Business employee rating is in line with the average (within 1 standard deviation) for employers within the Insurance industry (3.6 stars).

Reviews by job title

305 reviews
5.0
Feb 2, 2026

Growth Company Energy

Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

- Strong ties to customer mission and supporting small businesses - Recognizes impact > pedigree. Chance to make an impact across all levels of the organization. - High levels of ambition amongst employees. Genuine desire to grow SB and help protect small businesses - Genuine commitment to investing in and caring for employees - SB recently shifted to a pay for performance structure -- welcomed change!

Cons

- Emphasis on growth can create tension on investing in foundational programming - High energy isn't for everyone. Likely not well suited for those who like structure/process but rather cater to those who do well in ambiguity. - SB is still developing how to communicate, scale, etc. with a larger employee base and more complex organizational -- those who do well tend to know how to navigate the organization to get stuff done. SB is working to invest in these areas.

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Simply Business Response
4mo
Thank you for sharing such a detailed and thoughtful perspective on your time so far at Simply Business. It’s rewarding to hear that you’ve valued our focus on impact over pedigree and our recent shift to a pay-for-performance structure—we truly believe our people are our best advocates and that everyone, regardless of their level, should have the opportunity to make a meaningful mark here. We also appreciate your recognition of our commitment to caring for our team, as that remains a top priority even as we scale. We understand the tension between rapid growth and foundational stability. As we scale, we’re prioritizing clearer communication and simpler internal structures to make navigating our organization more intuitive. While our high-energy pace can create ambiguity, we view it as a chance to build better systems together. At the end of the day, helping small business owners succeed is what truly brings us together and makes our work so rewarding.
5.0
Feb 2, 2026

Collaborative Culture, Innovation Focused, Customer Driven

Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

SB cares about its employees and fosters an environment where everyone has a chance to grow and develop. The customer mission is really impactful and our offices create a warm, collaborative environment where all employees are welcome. Innovation is at the forefront of our work, with an annual hackathon open to all SBers.

Cons

None that come to mind.

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Simply Business Response
4mo
Thank you for sharing your experience working at our SB Boston hub; it’s fantastic to have had you on the team for over three years! We’re thrilled that you feel our warm, collaborative environment fosters growth, as we truly believe in caring and advocating for our employees. It’s great to hear that innovation and our annual hackathon resonate with you; we always aim to be inquisitive and look for new ways to learn. We’re also glad our customer mission feels impactful and that you find our workspace so welcoming. We hear your advice to management and will continue to be straightforward and honest about our business outlook and results to ensure everyone stays informed and motivated.
1.0
Jan 28, 2026

Don't work for this company

Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

Building your resume by doing way more than you're actually paid for

Cons

Leadership is TERRIBLE especially the most senior especially in the US. ZERO sympathy for people dealing with real life problems, leaders openly disregarding concerns, reorgs that make things worse, lay offs that make no sense, people doing work they aren't compensated or recognized for, terrible strategy, not competitive pay, have gotten rid of benefits that made it stand out, HR team is a joke, senior leaders aren't aligned at all and are either not qualified or just not good at their iobs

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Simply Business Response
4mo
We sincerely appreciate you taking the time to share your feedback, though we are saddened to read your review. Continuous improvement is crucial to us, and we take all feedback seriously. While we want to address your concerns here, we would also welcome a conversation for a deeper discussion. We were particularly disheartened by your comments regarding the care of our employees. We are fully committed to fostering an empathetic and supportive environment, striving to treat each employee with respect. Our five core values—Learning, Empowerment, Authenticity, Pioneering, and Simplicity—are embedded in our daily operations and embodied by our leadership and teams. Regarding compensation and benefits, we regularly conduct reviews of our total compensation and reward packages to ensure they remain competitive in the market. Finally, we understand that periods of change can be difficult, and we aim to be as transparent as possible. These decisions are not taken lightly and are typically tied directly to our clearly defined growth strategy. We value the hard work and dedication of all our past and present employees, and we again welcome any further discussions on the topics you have raised.
Viewing 22 - 24 of 305 Reviews

Glassdoor has 329 Simply Business reviews submitted anonymously by Simply Business employees. Read employee reviews and ratings on Glassdoor to decide if Simply Business is right for you.