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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Simply Business Compensation & Benefits in Boston

Updated on September 17, 2026

How are the compensation & benefits at Simply Business?

The Boston office is characterized by a comprehensive total-rewards offering that emphasizes ample time away, strong family support, and long-term savings. Together, these dynamics suggest the Boston location offers a balanced experience with meaningful benefits that support life outside work while strengthening overall employee security.

Key Insight for Candidates

At Simply Business Boston, the defining total-rewards pattern is unusually generous paid time off paired with formal paid sabbaticals and a clear 5% 401(k) match. This combination prioritizes rest and long-term financial security, complemented by hybrid flexibility and office perks like commuter benefits and catered lunches.

Evidence in Action

Generous Time Off — 25 days of vacation, 10 sick days, company holidays with floating days, and a paid sabbatical (two weeks after five years; four after ten) define time‑off norms. Boston employees can plan rest and longer resets confidently without sacrificing income.
Fidelity 401(k) Match — A 401(k) plan through Fidelity with a 5% employer match standardizes retirement savings support. Boston employees build long‑term wealth predictably, with company contributions boosting retirement balances automatically.

Positive Themes About Simply Business

Leave & Time Off Breadth: Boston-based materials highlight generous paid time off spanning vacation, sick time, company holidays, and a formal sabbatical program. Feedback suggests employees in Boston value the ability to unplug and take additional time for volunteering.
Parental & Family Support: U.S. and Boston listings describe a generous paid parental leave program with options for growing families, including adoption support. Feedback suggests Boston employees can take meaningful paid time to care for new children.
Retirement Support: Boston job profiles specify a 401(k) offered through a well-known provider with an employer match. Feedback suggests this retirement support is a notable part of total compensation for the Boston team.