Upwork Benefits Overview

Upwork proudly offers a comprehensive set of benefits to ensure employees are able to bring their whole selves to work. To allow for that, we aim to deliver world-class offerings and perks that cover your medical, dental, vision, emotional and family well-being. If you are an active, regular, full-time employee working a minimum of 20 hours per week you are eligible for all lines of coverage.

Health Insurance & Wellness Benefits

Flexible Spending Account (FSA)

Upwork provides an annual HSA contribution. You may also contribute pre-tax dollars to a Health Care FSA and Dependent Care FSA account.

Disability Insurance

Upwork offers both short term disability (STD) and long term disability(LTD) insurance.

Dental Benefits

Upwork provides your dental coverage through MetLife with a PPO plan offering.

Vision Benefits

VSP Vision offers a broad array of services for employees at Upwork.

Health Insurance Benefits

We offer Anthem Blue Cross PPO and HSA plans and you may choose the best plan for you and your family.

Life Insurance

Life Insurance coverage of 2X up to $300,000. Employees can also purchase coverage for a Spouse/DP and child(ren).

Pet Insurance

Nationwide Pet Insurance now provides coverage to all pets within your life!

Wellness Programs

Upwork offers an on demand mental health platform, Ginger.IO, along with a parenting support tool, Cleo.

Onsite Gym

Retirement & Stock Options Benefits


Upwork offers a traditional pre-tax 401(K) along with an after-tax Roth IRA option.

401(K) Matching

Upwork matches 50% of every dollar contributed by employees into their 401(k) up to $5,000 per year. Employers match is fully vested after 1 year of service.

Company Equity

Upwork offers equity as part of our standard compensation package.

Employee Stock Purchase Plan

We allow qualified employees to purchase company shares at a discounted price.

Performance Bonus

Child Care & Parental Leave Benefits

Child Care Benefits

Upwork offers dependent care flexible spending accounts. In addition, we offer a $100 monthly credit from Trusted for backup and emergency child care services.

Generous Parental Leave

Upwork provides employees time to bond with their newborn and family. We offer up to 12 weeks of fully Paid Parental Leave.

Remote Work Program

Upwork encourages a healthy work-life balance. For your convenience we allow you to work from home on Wednesdays.

Adoption Assistance

Upwork will reimburse up to $3,000 for eligible fertility or adoption related expenses per plan year.

Vacation & Time Off Benefits

Unlimited Vacation Policy

Upwork provides an Unlimited Time Off policy to further enhance our culture of trust and empowerment.

Generous PTO

Paid Volunteer Time

The Upwork Foundation has asked that 1% of employees time be used for giving back to the community and volunteering.

Paid Holidays

Upwork offers all employees paid time off to observe all major holidays.

Paid Sick Days

Perks & Discounts

Beer on Tap

We offer a variety of Beer and Wine.

Casual Dress

Commuter Benefits

You can elect up to max of $260 pre-tax for transit and parking. Upwork will match 50% of your pretax contributions each month.

Company Outings

Free Daily Meals

Upwork provides lunch on a daily basis from local Chicago restaurants.

Game Room

Stocked Kitchen

Upwork has a fully stocked kitchen including unlimited snacks, coffee, tea and all of the flavored LaCroix you can handle.

Happy Hours

Pet Friendly

Fitness Subsidies

We reimburse employees up to $50 per month for fitness related expenses. We have a corporate partnership with 24 Hour Fitness, but you can apply to your preferred gym or approved wellness expense.

Professional Development Benefits

Job Training & Conferences

Diversity Program

Diversity, Inclusion and Belonging is critical to the success of our business and our ability to further our mission of creating economic opportunities so people have better lives.
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