Year Founded: 2003

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Benefits at iboss

As part of the iboss team, you will be working with the best and the brightest in an atmosphere that’s both creative and challenging. We are devoted to excellence, and we foster an environment where performance is rewarded and collaboration is encouraged. iboss provides competitive and comprehensive benefits to its valued employees. iboss offers Medical, Dental, and Vision coverage, Short Term Disability, Long Term Disability, as well as FSA's, a Health Care Savings Account, and Life & AD&D Insurance to employees and their families. iboss also offers a very competitive 401k company match and vesting schedule. Join us in Boston and enjoy the free on-site gym membership, catered lunches, unlimited snacks, monthly charity events, quarterly outings, paid time off, company paid holidays, and much more! Step into an optimistic, supportive, and FUN work environment!

Financial + Retirement


401(K) matching

Company equity

Performance bonus

Office Perks

Commuter benefits

iboss offers pre-tax commuter benefits for all employees, as well as a free bike membership.

Company-sponsored outings

iboss hosts company outings Quarterly.

Onsite gym

Free snacks and drinks

iboss has a fully stocked kitchen including unlimited snacks, fresh fruit, coffee, tea, and more!

Some meals provided

On special occasions we will celebrate with free breakfast, lunch, and/or dessert!

Child Care + Parental Leave

Company sponsored family events

Acme co. sponsors family oriented events Quarterly.

Family medical leave

Generous parental leave

Health Insurance + Wellness

Dental insurance

Disability insurance

iboss offers both Short and Long Term Disability benefits to it's eligible employees.

Flexible Spending Account (FSA)

iboss employees can contribute the maximum allowed per the IRS to their Medical FSA's. Dependent Care FSA's and Commuter FSA's.

Health insurance

Life insurance

Team workouts

Vision insurance

Wellness programs


Documented equal pay policy

Mean gender pay gap below 10%


Volunteer in local community

iboss provides its employees the opportunity to give back through monthly charity events.

Open door policy

Open office floor plan

Partners with nonprofits

iboss partners with Building Impact, Clean the World, Operation Gratitude, Paws for Ability, First Teacher, Housing Families, Price Center, New England Center and Home for Veterans, Hearth, and more!

Team based strategic planning

OKR operational model

Vacation + Time Off

Generous PTO

Paid volunteer time

Paid holidays

Paid sick days

Professional Development

Promote from within

Lunch and learns

iboss hosts lunch and learns for various employee benefit programs including the Equity Program, 401k program, etc.