Simply Business
What's It Like to Work at Simply Business?
Frequently Asked Questions
Simply Business supports job satisfaction by giving employees practical reasons to feel engaged in the work they do each day. The strongest satisfaction themes come from ownership, visible appreciation and support systems that help employees feel invested in both the work and the people around them.
- Ownership that starts early: Simply Business gives employees opportunities to contribute before they have spent years inside the organization. A senior software engineer said he felt welcomed during onboarding and helped launch a new insurance carrier within two months, showing how quickly employees can become part of meaningful business work.
- Recognition that reinforces belonging: Simply Business makes employee contributions visible through company forums and leadership recognition. A director of financial planning and analysis said professional achievements made her feel “more confident, engaged, satisfied, motivated, and deeply invested in the work I do and the people I work with,” after being recognized as a U.S. Inspiring Leader.
- Support that makes work sustainable: Simply Business strengthens job satisfaction through rewards and benefits that support employees beyond the workday. The company provides market-informed pay, bonus eligibility and a 401(k) with a 5% employer match, while also emphasizing employee wellbeing as part of the broader experience.
- External signals:
- Employee satisfaction: Employees surveyed on external review sites describe Simply Business as a strong workplace with authentic people and genuine management investment in employees. Reviews also point to optimism about role growth. (Comparably; Indeed)
- Employee experience: External reviews highlight strong vacation time, benefits and a people-first environment as reasons employees value the workplace. (Indeed; Blind; Comparably)
Bottom line: Simply Business supports job satisfaction by helping employees feel trusted, recognized and supported in ways that make their day-to-day work feel meaningful.(Simply Business careers page; employee interviews; external review data)
Yes, Simply Business is a strong workplace for employees who value meaningful customer impact, trusted teams and a company that is still evolving its digital insurance marketplace. Employee feedback and external ratings point to a positive experience, especially around people, flexibility and the ability to contribute meaningfully.
- Supportive and people-focused culture: Simply Business emphasizes creating an environment where employees feel supported, included and able to do their best work. The company highlights collaboration, openness and a commitment to helping employees grow professionally. A director of insurer relations said the company creates an environment “where individuals feel comfortable sharing their talents and voicing their opinions without fear of negative repercussions or infringing on others’ roles.”
- Purpose-driven work: Employees have opportunities to contribute to a business that helps small businesses find and manage insurance coverage. The company emphasizes connecting individual work to broader customer outcomes, helping employees see the impact of their contributions.
- Investment in employee growth and wellbeing: Simply Business supports employees through professional development opportunities, recognition programs and benefits designed to support well-being. These practices help create an environment where employees can build long-term careers while maintaining work-life balance.
- External signals:
- Why employees recommend it: Employees surveyed on external review sites describe Simply Business as a workplace people recommend because of its people-first environment and positive company direction. Reviews also point to access to senior leadership and employee engagement as reasons the company stands out. (Indeed; Glassdoor)
- Review and culture data: External review data shows a 4.7 out of 5 rating for work-life balance. External workplace data also gives Simply Business an A- overall culture score and top-15% retention ranking among similarly sized companies. (Blind; Comparably)
Bottom line: Simply Business is recommended by employees who value customer-focused work, supportive teams and meaningful opportunities to contribute as the company grows. (Simply Business careers page; employee interviews; external review data)
Simply Business's Candidate Tradeoffs
If you’re weighing whether Simply Business is the right fit, these are the core tradeoffs to consider.
- Simply Business places greater emphasis on autonomy paired with clear accountability and measurable standards than on loosely defined roles with flexible performance expectations.
Simply Business Employee Reviews
What People Are Saying About Simply Business
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Mission & Purpose: Work centers on simplifying insurance for micro and small businesses, making day‑to‑day contributions feel customer‑centric and meaningful. Feedback suggests the mission resonates with people who want visible impact for entrepreneurs.
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Work-Life Balance: Flexible, hybrid ways of working with hubs and remote options give teams latitude to choose how they collaborate. Feedback suggests this flexibility is a consistent plus for many roles.
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Market Position & Stability: Being part of a large parent company provides scale and brand stability in a regulated industry. Feedback suggests this backing de‑risks the environment compared with early‑stage startups.
Simply Business's Benefits
Company or teams have recognition rituals for individual work
Employee feedback used to shape policies and strategy
Encourages autonomy and ownership from employees
Established employee awards to honor work and contributions
Managers give public shoutouts and celebrate employee milestones
Provides modern technology across teams
Provides resources to build team camaraderie
Quarterly engagement surveys to gauge employee satisfaction
Documented path to leadership development
Encourages lateral mobility to expand skills and impact
Promote from within
Provides customized development tracks
Defined values and mission statements
Engineering team utilizes pair programming
Hosts in-person all-hands meetings
Simply business has monthly town hall meeting and quarterly all hands meetings.
Implements team-based strategic planning
Leadership encourages open, transparent debate
Mistakes are treated as learning opportunities
Open office floor plan to encourage communication and collaboration
Prioritizes mission-driven work in decision-making processes
Prioritizes real-world impact of work in decision-making processes
Promotes a people-first, social culture
Uses an OKR operational model to clearly define goals and priorities
Utilizes an open door policy that encourages accessibility
Async-friendly policies, culture that encourage work flexibility
Offers a remote work program
Provides work from home flexibility
Utilizes a flexible work schedule
Utilizes a hybrid work model
