Simply Business

Simply Business

Boston, MA
1,000 Total Employees
300 Local Employees
Year Founded: 2005

Benefits at Simply Business

What are the benefits? Here are some of the great benefits and perks that come from being a Simply Business employee: • A salary that reflects your experience, our pay policy, and the market we’re in from your first day • Group plan for medical, dental, vision, and prescription drug coverage • Short term disability, long term disability, and life insurance coverage • Participation in the Company’s bonus program • Participation in 401(k) plan with a 3% employer match • Commuter benefits to help cut down on parking and public transit costs • 25 days of vacation time plus 10 sick days and 8 company holidays, and 2 floater days • A genuine investment in your learning and development • Annual company trip, regular outings, and volunteer opportunities • Generous Parental Leave program, for your growing family • Focus on employee wellbeing with a membership to TalkSpace • An awesome WeWork office with cold brew coffee and other beverages on tap, local pop-up events, and more Simply Business is an equal opportunity employer. We're committed to welcoming and helping to grow employees within an inclusive & diverse culture. And that commitment starts with our interview process. Once you apply, your info will be reviewed in a committee with employees from different levels, teams, and experiences. We pride ourselves on fostering a sense of community, which is only made stronger by each individual at SB, so you'll have the opportunity to meet a variety of people throughout the process. Get excited! Want more info on working at Simply Business? Check out our careers page: What's going on with work from home and return to the office? More and more, people are talking about going back to the workplace and the new normal. At Simply Business, we’re thinking of it as a Better Normal. That means offering our SBers more choice and greater flexibility to work in a way that’s best for their particular job, their teams, and their lives. We’re shifting to a hybrid working model, so we’ll have employees working virtually and in the office at any given time. We’re also aware there are times when working together in person is the best way to get things done. We expect our SBers to connect in their hubs (that’s what we call our offices) most likely four times a month. That said, there’s no one-size-fits-all solution, so we expect all SBers and their teams will find the operating rhythm that works best for them. If you’re wondering what it might be like for you at Simply Business, our Talent Acquisition is happy to answer any questions. In fact for them, it’s perfectly normal. Most of our interviews will still take place over Zoom (however, depending on the role, there may be the opportunity/expectation to meet members of the team in-person). If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom – you’ll need WiFi and a laptop, or a 4G-enabled smartphone. If you don’t have access to either of these, or you need support with your application, get in touch with us at [email protected]. Similarly, please email us with any questions or if you want to pause your application for a bit – we’ll be happy to keep you updated on future opportunities like the one above.

Financial + Retirement


401(K) matching

Performance bonus

Office Perks

Commuter benefits

Company-sponsored outings

Monthly "First Thursday" events have included bowling, museums, food tours, Halloween parties, and more. Something different happens every month!

Company-sponsored happy hours

Onsite gym

Onsite office parking

Recreational clubs

Free snacks and drinks

Some meals provided

Simply Business provides a weekly catered lunch on Wednesdays.

Home-office stipend for remote employees

Mother's room

Child Care + Parental Leave

Company sponsored family events

Our "Simply Scary" Halloween party brought together the families of our team for costumes, trick or treating, cookie decorating, a photo booth, and more!

Family medical leave

Employees who have been with the company for 12 months are eligible for :param:2 weeks of family medical leave.

Generous parental leave

We provide up to 12 weeks of parental leave for the primary caretaker. Acme Co. also provides 12 weeks of leave for the secondary caretaker.

Return-to-work program post parental leave

Professional Development

Customized development tracks

Job training & conferences

Acme Co. offers employees professional development opportunities like Onsite training courses, The ability to attend job related conferences and seminars.

Mentorship program

Online course subscriptions available

Paid industry certifications

Promote from within

Lunch and learns

Acme Co. hosts lunch and learn meetings :param:1.

Continuing education available during work hours

Tuition reimbursement

Personal development training


Dedicated diversity and inclusion staff

Diversity manifesto

Mandated unconscious bias training

Diversity employee resource groups

Hiring practices that promote diversity

Diversity recruitment program

Health Insurance + Wellness

Dental insurance

Disability insurance

Flexible Spending Account (FSA)

Health insurance

Life insurance

Team workouts

Vision insurance

Wellness programs

Mental health benefits


Volunteer in local community

Simply Business has volunteered with Rebuilding Together, Greater Boston Food Bank, and more.

Flexible work schedule

Open door policy

Open office floor plan

Pair programming

Partners with nonprofits

Remote work program

Team based strategic planning

OKR operational model

Employee resource groups

Quarterly engagement surveys

Hybrid work model

In-person all-hands meetings

Employee awards

Vacation + Time Off

Generous PTO

Simply Business offers a generous 25 days of vacation per year for all employees.

Paid volunteer time

Paid holidays

Paid sick days

Employees receive 10 sick days per year.


Eligible employees get 2 weeks of paid sabbatical after 5 years at SB and 4 weeks of paid sabbatical after 10 years at SB.

Floating holidays

Bereavement leave benefits

Search the 4 jobs at Simply Business

9 Days Ago
Fintech • Information Technology • Insurance • Software
The Product Manager will join the Digital Product team in Boston, MA and work on creating straightforward and personalized ways for small businesses to research, buy, and manage insurance online. They will collaborate with cross-functional stakeholders, oversee product delivery, and ensure a constant stream of value through the agile development lifecycle.
Fintech • Information Technology • Insurance • Software
Seeking a Senior Legal Counsel to handle a wide range of legal matters with a business-focused approach and simplify complex issues. Responsibilities include drafting agreements, advising on employment, managing disputes, and maintaining corporate policies. Requires 5-7 years of experience, J.D., state bar admission, and excellent interpersonal skills.
Fintech • Information Technology • Insurance • Software
The Brand Marketing Manager will be responsible for implementing brand strategy, leading social and PR initiatives, and championing the brand across the organization. They should have 6-10 years of marketing experience, including experience managing creative and campaign development, social media management, and communications.