Companies Simply Business

Simply Business

Boston

1,000 Total Employees

Year Founded: 2005

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Marketing 2 Finance 1 Operations & Support 1

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What's It Like to Work at Simply Business in Boston?

Updated on September 17, 2026

What's it like to work at Simply Business?

The Boston office is characterized by hybrid flexibility supported by a refreshed downtown hub and a U.S. benefits package that emphasizes comprehensive well‑being. Together, these dynamics suggest the Boston location offers a balanced, well‑supported environment anchored by the stability and resources of its Travelers parent.

Key Insight for Candidates

Boston’s hub-centric hybrid model—anchored by a refreshed downtown headquarters—blends flexibility with periodic in‑person collaboration. This strengthens a close‑knit, problem‑solving culture and increases visibility to approachable leaders and learning rituals (mentoring, workshops, hackathons), giving candidates both autonomy and meaningful connection in the U.S. hub.

Evidence in Action

Hybrid Hub Attendance — An expectation of coming into hubs a minimum of four times a month shapes Boston’s hybrid rhythm. It creates predictable in‑person touchpoints at 53 State Street while preserving flexibility for focused remote work and easy cross‑team collaboration.
Annual Hackathons Culture — Innovation is encouraged through annual hackathons that include Boston participants. Employees get hands‑on time to test ideas, showcase skills, and influence product improvements in a supportive, cross‑functional setting.

Positive Themes About Simply Business

Work-Life Balance: The Boston HQ operates within a hybrid, hub-based model that allows flexibility to work remotely or from the downtown office, paired with generous time off highlighted for U.S. employees. The refreshed State Street space also supports in‑person collaboration when needed.
Benefits & Perks: U.S. employees in Boston are offered comprehensive medical, dental, and vision coverage, mental‑health resources, flexible parental leave, generous time off, bonus eligibility, and a 401(k) with employer match. These offerings are available to the Boston‑based U.S. team.
Market Position & Stability: The Boston location serves as the U.S. headquarters of a Travelers‑owned business, giving the team the scale and resources of a major insurer. Company updates also point to continued investment in the Boston hub, including the recent HQ move downtown.