Chicago, IL
65 Total Employees
Year Founded: 2010

Benefits at BenchPrep

BenchPrep provides a full suite and a wide variety of benefits and perks. While our competitive medical benefits and 401(k) contribution are nothing to dismiss, it’s the extras that really set us apart. We provide an annual $1,200 learning stipend, Flex PTO (our version of unlimited PTO), Summer Hour Fridays, 8 wellness days to focus on physical health AND mental health, a $500 new hire stipend to set up your home office, and $25 each month after that. We also have a generous parental leave program, and have no meeting days each sprint, and no meeting periods Friday afternoons during non-Summer Hours to ensure deep focus time. Lastly, we are a remote-first organization, giving our employees the flexibility to work from wherever in the U.S. makes most sense for them. Although we are remote-first, we do still have an office space for employees to use should it be preferable to them. Finally - twice a year we bring the entire team into our space in Chicago for a 3 day office retreat, where we spend time on collaboration, learning, and simply having fun with each other. Scroll down to learn more about those items and see what else BenchPrep has to offer.

Financial + Retirement


BenchPrep’s 401k retirement plan offers a a cost effective employee retirement plan. The plan offers Roth and Pre-tax Investment options..

401(K) matching

BenchPrep contributes 3% of an employee’s annual base salary, regardless of how much the employee contributes, which is immediately vested.

Performance bonus

Office Perks

Commuter benefits

Transit and Parking benefits: Employees may elect up to $260/month for pre-tax allocation for mass transit & parking expenses for commuting to BenchPrep, including Metra, Ventra and parking facilities

Company-sponsored outings

BenchPrep has regular outings that include Cubs rooftops, boat trips on Lake Michigan, off-site happy hours, poker nights, game nights, foodie dinners, and a holiday party, among other events.

Fitness stipend

Employees have access to the Willis Tower's exclusive 35,000 sq. ft gym for $10/month.

Free daily meals

We provide a $12.50 daily stipend for employees every day via Fooda for those in office. (

Company-sponsored happy hours

We have a standing in-office happy hour that starts at 4:00 PM on Fridays, but never feel constrained to limit this into being a once a week occurrence.

Onsite gym

Free snacks and drinks

FULLY stocked! Beverages = Soda, Coffee, Tea, RedBull, Juice, Vitamin Water, etc. Food = if you can think of the snack, we probably have it or some variation. Employees will never go hungry here.

Some meals provided

Home-office stipend for remote employees

New hires receive a one-time payment of $500 to setup their home office and $25/month every month after that to aid in monthly home expenses.

Meditation space

Mother's room

Professional Development

Continuing education stipend

Customized development tracks

Job training & conferences

Employees are provided an annual stipend to attend external training evens or conferences.

Online course subscriptions available

Paid industry certifications

Promote from within

Lunch and learns

Continuing education available during work hours

Health Insurance + Wellness

Dental insurance

BenchPrep offer 3 dental plans.

Disability insurance

Our plan coverage offers employees Short Term Disability coverage at 60% of their weekly salary with a $2,500 weekly max. Long Term = 60% of their monthly salary with a $10,000 monthly max.

Flexible Spending Account (FSA)

Pre-tax dollars can be set aside for medical, dental, and vision ($2,750/yr) for employees or dependents with or w/o enrolling in our insurance program. Daycare & elder care allows for up to $5,000/yr

Health insurance

BenchPrep’s health insurance plan with BCBS of IL has a low deductible and BenchPrep pays 90% of the monthly premium for employees AND their dependents.

Life insurance

Up to 3x annual salary, $750K max of voluntary life insurance & accidental death & dismemberment insurance. Spouse & dependent children plans available too.

Pet insurance

Vision insurance

BenchPrep’s vision insurance plans provide annual eye exams for a $10 copay and a $130 allowance toward frames and/or contacts.

Wellness programs

Mental health benefits

Wellness days

These days are designed to allow employees to take time off for self-care and to focus on their physical and mental health.


Volunteer in local community

Flexible work schedule

BenchPrep offers flexible work schedules as needed for employees. It allows for greater work-life balance and can lead to increased job satisfaction and productivity.

Open door policy

Open office floor plan

Pair programming

Partners with nonprofits

Remote work program

BenchPrep offers Remote Work as an option for employees. This also allows employees to better balance their work commitments with personal and family needs.

Team based strategic planning

Day off for your birthday

We acknowledge and celebrate employees on their special day, and encourage them to utilize this special benefit by spending quality time with loved ones, and/or doing the things they enjoy the most.

Hybrid work model

Summer hours

Child Care + Parental Leave

Family medical leave

Generous parental leave

BenchPrep offers generous paid parental leave for new parents with at least 1 month of service, including a paid leave policy for foster parents.

Return-to-work program post parental leave


Highly diverse management team

Mandated unconscious bias training

Hiring practices that promote diversity

Diversity recruitment program

Vacation + Time Off

Paid volunteer time

Paid holidays

Paid sick days

BenchPrep employees receive 5 sick days per year in addition to their PTO.

Unlimited vacation policy

Flexible time off

Bereavement leave benefits

Company-wide vacation

The company is closed during the week between Christmas and New Year's to allow employees to relax, spend quality time with family/friends, and recharge, and contribute to their overall well-being.

Additional Perks + Benefits

Competitive salary, company sponsored 401(k) • Fun, meritocratic, mission driven, dynamic work culture • Commitment to fostering positive office culture (included, but not limited to, monthly company dinners, quarterly outings, an in-office ping pong table, cocktail hours, poker nights, etc.)

Search the 3 jobs at BenchPrep

Recently posted jobs

2 Days Ago
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As the Revenue Growth Manager, you will partner with Customer Success and Marketing teams to identify growth opportunities, expand relationships, and create action plans for revenue expansion. This role involves strategic selling, defining upsell potential, and designing sales strategies for existing customers. Key responsibilities include working with CSMs, identifying expansion challenges, and collaborating with delivery teams to inform growth opportunities.
9 Days Ago
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Edtech • Enterprise Web • Software
As an Implementation Manager, lead and manage software implementation projects for new and existing customers. Collaborate with multiple resources and customers to deliver project outcomes and provide consultations on BenchPrep platform features and applications.
16 Days Ago
Chicago, IL + 77 More
Edtech • Enterprise Web • Software
Remote Staff/Senior Accountant position at BenchPrep responsible for maintaining accurate financial records, analyzing data, and ensuring regulatory compliance. Key responsibilities include managing accounting functions, analyzing expenditures, and preparing financial statements. Ideal candidate has 3-5 years (Staff Accountant) or 5-8 years (Sr Accountant) of experience in accounting or auditing, with a Bachelor's degree in accounting and CPA preferred.