One of our primary goals here at Fiveable is to support our team and provide everything that is needed for our teammates to be at their best, healthiest self, both physically and mentally. And while we are proud of the benefits that we are able to offer, we are also constantly learning more about what resources and benefits we can provide, so if you have any suggestions or feedback on what's missing, we'd love to hear your thoughts!

🏝 Vacation and Time Off

Discretionary Time Off, All Federal Holidays Off, Parental Leave, and Space for other types of leave

We operate with a Discretionary Time Off policy - This is a slightly modified version of Unlimited Time Off, where there is no limit to the time off you take, as long as you and your manager are in agreement with the time off period. We do however recommend a minimum of at least 3 weeks Time Off per year, in addition to all federal bank/religious/public holidays.

We also understand that life goes on, so we encourage teammates to take the time they need for Sick Leave, Volunteering, Voting, Bereavement, and other life circumstances that occur, on top of a 12-week fully-paid parental leave policy.

Lastly, we recently implemented company-wide Wellness Days: days where the entire company can unplug from work and focus on overall wellbeing. These take place every 4th Friday of the month, and the entire company is “closed” for the day.

🏥 Medical Insurance

100% Employer-Paid Plans across Health, Dental, and Vision for Team Members and Dependents

We offer comprehensive, 100% employer-sponsored medical insurance across Health, Dental, and Vision for all of our Full-Time teammates and their dependents.

All of our Medical Insurance plans are through Aetna, and we offer a variety of plans, including HSA-eligible plans, High-Deductible plans, POS's, EMO's, and HMO's. Plans go into effect on the 1st of the month after a team members start date.


All teammates who enroll in a Medical Insurance plan with us also gain access to a free Talkspace membership, which is an online therapy service that enables team members to connect with a licensed therapist through text, voice, and/or video.

💻 Equipment

New Laptops with a 2-year rotation


Fiveable provides laptops for all new teammates starting from day one. We also have a 2-Year Ownership program in which every 2 years, ownership of a laptop transfers from Fiveable to the Team Member, at which point the team member is eligible to refresh and re-enroll in the 2-Year Ownership plan again.

While specific computer builds will be left up to the hiring manager to decide for their team, we primarily use Apple equipment across the board.