Insurance
We offer our employees the following insurance benefits:
- 3 levels of Blue Cross Blue Shield Health Insurance for employees and dependents, 50% covered by Online Optimism—no matter which plan you choose.
- Blue Cross Blue Shield Dental Insurance for you and dependents, 50% covered by Online Optimism.
- Vision and Life Insurance, 100% covered by Online Optimism.
- SIMPLE IRA retirement plans with 3% employer match.
- After your first year of employment, 16 paid weeks of maternity leave, and 8 paid weeks of paternity / adoptive parental leave, once per year.
- An Employee Assistance Program for mental health counseling.
PTO + Holidays
All Optimists receive 15 paid vacation days each year. Once you reach your fifth-year workaversary with Online Optimism, you receive 20 paid vacation days each year.
All Optimists can also take a half day any day during our birthday weeks.
In the summer, all Optimists get four Summer Fridays, which are Friday half days throughout June to August.

We take the following holidays off each year. Religious holidays, marked with an *asterisk*, may be shifted around per employee’s wishes.
- New Year’s Day
- *Recover-From-Muses Friday
- *Lundi Gras
- *Mardi Gras
- *Good Friday
- Memorial Day
- Juneteenth
- July 4th
- Labor Day
- Thanksgiving
- Black Friday
- *Christmas Eve
- *Christmas Day
- New Year’s Eve
In addition, staff receive unlimited sick days.
#FlexTime
Our regular office hours are from 9am to 5pm every weekday, local time. We also have the option of flexible work hours, which we call flex time.
- Super Flex: 7am–3pm
- Flex: 8am–4pm
- Half Flex: 8:30am–4:30pm
- Lunch Flex: 8am–5pm, with a 2-hour lunch
- Late Flex: 10am–6pm*
* When working late flex hours, you must set your status the evening before to let everyone know you’ll be working those hours.

Bonuses
All employees receive annual holiday bonuses, aligned with the amount of time they have been with us and their efforts given to the company in the previous calendar year.
Optimists also receive bonuses depending on how many KPIs they achieve every trimester. While these aren’t cash bonuses, they are offered as tickets to local events, to encourage employees to immerse themselves in their community.
Internet + Phone Stipends
Because employees use their personal cell phones to contact clients, we give monthly reimbursements of $50/month to cover any fees we may incur on employees’ cell phone bills. We also provide Internet stipends ($30/month in New Orleans; $35/month in Atlanta and DC) to cover the Internet used for remote work.