Best Gig Jobs of 2019 That Offer Benefits

According to the United States Bureau of Labor Statistics (BLS), the gig economy is on the rise. As more companies begin to take on independent contractors, the glaring differences between contract work and full-time employment become more obvious.

In particular, contracted employees are generally not offered employee benefits packages, including time off. If not supplied with vision, dental or medical insurance through an employer, workers who want coverage must pay for it out-of-pocket.

Federal and state regulations make it difficult for employers to offer benefits to contract workers because offering certain benefits implies permanent employment by one company. Yet, many people continue to pursue these positions due to the many personal benefits of doing gig work, such as the flexible schedules. Some companies are finding ways around these laws in order to support their contracted workers. Below is a list of the best gig jobs of 2019 that offer benefits.


SurveyMonkey is an online survey company established in 1999. Through this company, organizations and individuals can create online polls to measure opinions about products, services and more. Since its inception, SurveyMonkey has consistently grown and branched out, becoming one of the most trusted sources of public polling information. For example, SurveyMonkey was the only online survey company to have polls that accurately predicted the outcome of the 2015 British election.

According to the company’s representatives, over 300,000 organizations use its services. It consistently caters to those clients by offering unique and innovative survey options. In 2018, SurveyMonkey’s parent company SVMK Inc. made its debut on NASDAQ. The same year, SurveyMonkey decided it wanted to cater to certain freelancers who help the company thrive as well. To do so, it began offering benefits to contracted workers.

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The move attracted a lot of media attention, because many similar companies do not offer such benefits. However, the benefits are currently only offered to contracted workers at the San Mateo, California SurveyMonkey headquarters. Company representatives note the move is a result of full-time employees lobbying for the rights of contracted workers within the company. Benefits offered include:

  • Transportation expense coverage.
  • Paid time off.
  • Medical insurance.
  • Dental insurance.
  • Vision insurance.


Another company extending benefits to freelance workers is Uber. Uber is a ride-sharing company that hires gig workers to operate in a taxi-like capacity, transporting Uber users to desired destinations. The company’s workers can typically set their own hours and choose which gigs they want to accept. Benefits the company offers to gig workers include:

  • Health insurance selection assistance, through a phone app called Stride Health.
  • Discounted vehicle maintenance fees.
  • Tax services.
  • Phone plans.

Those benefits and the flexible nature of ride-sharing make this a popular company for gig workers. However, experts caution that Uber is often questioned, and occasionally sued, over its business practices regarding the status of these workers. Court rulings are often inconsistent when these issues arise.

For example, both a New York and Philadelphia court ruled on employee status at the company in 2018. In New York, workers were granted employee status, while workers in Philadelphia were ruled independent contractors. Health insurance and other general benefits may change, along with tax benefits, as the relationship between Uber and its workers is more clearly defined across the country.


Wonolo is an online website providing gig staffing solutions to certain industries, such as warehouse work. Currently, it has established offices in Vietnam and the Philippines, with a U.S. base of operations located in San Francisco. However, U.S. Wonolo users can participate in the program while based in multiple cities across the country. The list of available cities is subject to expansion. As of January, 2019 it is as follows:

  • Chicago, IL
  • New York City, NY
  • Los Angeles, CA
  • Atlanta, GA
  • Nashville, TN
  • San Antonio, TX
  • Dallas/Fort Worth, TX
  • Columbus, OH
  • Tampa, FL
  • Philadelphia, PA
  • Seattle, WA

Gig workers who join Wonolo are screened to ensure they fit the qualifications of the companies hiring. Company representatives can also view worker histories and ratings to gain insights into their capabilities. Through this process, the Wonolo service can help a business find new contract workers within hours while other forms of hiring can take weeks.

Related article: Different Types of Employee Fringe Benefits

Wonolo workers have the ability to work by the hour or by the day to accommodate their personal schedules and needs. They are also provided with several benefits, including:

  • Free access to the Stride Health app to help them acquire affordable health insurance.
  • Insurance coverage for work-related accidents.
  • PerkSpot discount program benefits, including grocery and travel discounts, after performing at least five Wonolo gigs.
  • Coaching and educational assistance for career advancement.
  • A five percent bonus for each job performed after achieving Wonolo Ambassador Program qualification status.


Fiverr is a website launched several years ago as online freelancing continued to grow. The initial mission statement of the company was to connect freelancers with employers in need of gig work. The unique business approach was each small gig paid exactly $5. Today, Fiverr offers gigs of all sizes and price ranges. Gig workers can post their services on Fiverr, so users in need of services can search listings by categories to locate contract workers to suit their needs. Available listings span multiple industries, including:

  • Writing.
  • Translation.
  • Animation.
  • Graphics and design.
  • Business.
  • Programming.
  • Music and audio.

In 2018, Fiverr launched is Elevate program. Fiverr Elevate provides its gig workers with multiple benefits options. Basically, the service offers advice on how gig workers can obtain affordable benefits. It utilizes a combination of short videos and discount service suggestions to help gig workers access the benefits desired.

For example, workers can receive tips on how to file taxes as independent contractors, followed by links to discounted tax services. The service is the product of Fiverr executives working directly with partner companies in related fields, such as law and healthcare.

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