Product Case Study — Portable Benefits for Gig Economy Workers

 Ensured is a product concept to bridge the gap of gig workers lacking benefits by providing healthcare and insurances through community funding to overcome regulatory friction over employment classification


Uber, Lyft, DoorDash, Grubhub, Postmates, and InstaCart. It’s likely you’ve placed an order from one of these household names, though have you considered what it’s like to be a gig worker? While gig workers appreciate the flexibility to dictate their own hours based on their individual needs, a survey from AppJobs revealed that 70% are unsatisfied with their lack of benefits, especially when it comes to health insurance, sick leave, and unemployment.

That statistic is staggering when you consider there are 57 million independent contractors in the United States, with 10.6 million citing contract work as their primary income source, according to the Bureau of Labor Statistics. The shift to alternative work arrangements will likely only increase with the future of work. One of the more vulnerable segments is app-based drivers, who often earn below minimum wage. App-based drivers disproportionately belong to lower economic brackets, are more likely to be African American or Hispanic than the national averages, and don’t receive employer benefits. The failure to provide gig workers with this financial safety net stems from a lack of sophisticated regulation, hampering the efforts of key players aspiring to move the needle on benefits.

The Problem

Sponsored benefits are traditionally tied to full-time employment, which neglects the healthcare needs of gig workers. A 2019 survey by Edelman found that 43% of freelancers cannot work a traditional job due to health care issues. This catalyzes a social inequality issue — a lack of benefits diminishes health outcomes for gig workers that are traditionally lower-income, diverse, and in great need of healthcare services.

So why haven’t more gig platforms provided benefits? While companies like Uber have voiced a desire to, antiquated laws penalize them for doing so. In many states, a gig platform paying for benefits could render their workers employees rather than independent contractors. This would entirely disrupt the economics of gig platforms by undermining workers’ job flexibility and right to claim some expenses against their taxes, plus result in costly payroll taxes for companies and higher consumer fares. Gig platforms are effectively disincentivized from offering benefits, leaving gig workers disempowered.


Through our problem identification, we developed several goals:

  1. Create an opportunity for gig workers to receive benefits through their gig platform
  2. Remove regulatory friction for gig platforms to provide benefits
  3. Provide an affordable suite of needed benefits
  4. Create ease in their ability to access and understand benefits

Understanding User Demographics

Considering our problem space and our goals to provide benefits to gig workers, we identified 3 potential user groups:

  • All Independent Contractors
  • App-Based Independent Contractors
  • App-Based Drivers

We were able to narrow our targeted user base down to app-based drivers through our market research.

First, when we dug into these 3 groups, we found that app-based drivers were more likely to be racially diverse and in need of benefits than other groups. COVID-19 has accentuated this need, as many put themselves at risk delivering meals and services to families who are able to shelter in place.

Second, we found that corporate greed wasn’t driving the lack of benefits for drivers. Many gig platforms have publicly stated they want to provide more benefits. They are only limited by the legal landscape around worker classification — providing benefits counted against their classification argument of keeping their drivers as independent contractors. Solve that, and you create benefit opportunities for a large swath of Americans.

Third, servicing app-based drivers meant that with only a few partnerships, we would gain access to a sizeable number of Americans in need of benefits.


Based on our market research, we hypothesized that app-based drivers would be most underserved and in need of benefits. We conducted 10 user surveys of both app-based drivers and other freelancers to validate our hypothesis. Main pain points from app-based drivers can be summed up as:

  1. Lack of healthcare
  2. Low pay
  3. Lack of retirement benefits

Meanwhile, pain points from general independent contractors can be summed up as:

  1. Career-related problems (mobility, recognition, work selection)
  2. Lack of healthcare
  3. Better client interactions

These findings were consistent with market research from the Journal of Economic Perspectives, where 50% of self-employed workers indicated healthcare was their most preferred social program.


Based on our user interviews, we constructed two user personas. Evelene is a DoorDash driver who needs to provide for her family and is concerned about the cost of healthcare. Craig is a commission-based designer who desires to find more freelance work and earn enough to cover personal expenses, though doesn’t have insurance nor understand it. These personas closely reflect our user research findings. The app-based drivers voiced more pain around benefits, while other freelancers mainly desired to earn more income and were less concerned about benefits. As a result, we prioritized targeting app-based drivers as our primary user group, given the greater importance of having benefits to them than other independent contractors.


We mapped the current user journey of an app-based driver signing up for health coverage to identify the primary pain point to address with our product: drivers paying out of pocket for health coverage. We also included the high-level journey of our proposed solution below to highlight how it solves the pain point.

Competitor (Stride Benefits)

Pain Point: User has to pay out of pocket for benefits

Our Solution (Ensured)

Bridging the Gap: User’s benefit plan will be covered by customer contribution of 2.5% on services

Solution Ideation

Prior to landing on our final solution, we ideated 3 solutions. In our market research, we uncovered that portable benefits offer a paradigm shift in the gig economy. Portable benefits are tethered to an individual rather than an employer. Under this model, gig workers retain flexibility without sacrificing benefits and employers can offer benefits without drastic cost increases and while minimizing exposure regarding employment classification. Considering this, all our solutions offer benefits portability, though solve the pain point of affordability to varying degrees:

We found that Solution 3 best addresses our goals of creating an opportunity for gig workers to receive benefits, removing regulatory friction, and providing affordable benefits and ease of access. It enables gig platforms to provide relevant benefits to drivers through funding from riders in order to support gig workers while reducing regulatory risk. Gig workers will have the ability to aggregate funds across gig platforms and the autonomy to choose benefits that best suit their needs and circumstances.

Despite the more challenging trade-offs and level of effort, we believe the partnership hurdle is limited as potential app-based partners have expressed the desire to provide a benefits suite directly, so long as they would not be penalized by the repercussions to the drivers’ worker classification.


To pressure test whether Solution 3 would be financially viable in covering the cost of benefits through community funding, we used the 2.5% rider fee established by the New York Black Car Fund to estimate the average contribution amount a full-time driver could earn from their riders per month. Seeing this was sufficient to cover the cost of a full benefits package (e.g. healthcare, vision, dental, and rideshare insurance), we validated the ability to offer added bonuses: funded healthcare coverage up to 6 months after unemployment by charging a small markup on the plan costs, plus the ability for drivers to pocket excess contributions. Our revenue model would consist of a small processing fee on contributions and a cut of benefit revenue from insurers.

Minimum Viable Product

We arrived at our Minimal Viable Product by creating a list of user stories, prioritizing those stories, and detailing a user experience flow that solved their needs. Our high-fidelity prototype focuses on allowing drivers to charge their customers directly through their business partner’s application, selecting a suite of benefits, and moving excess contributions to their bank account.

Homepage for our portable benefits platform. Full prototype here

We generated the following user stories to inform the core functionality for our MVP:

“As a user, I want to see the program structure and benefits explained simply to decide if I should join”

Feature: Homepage explaining the 2.5% earn structure from customers towards benefits, and benefits pages explaining coverage in simple language

“As a user, I want my gig platform to provide me with benefits.”

Feature: Partner integration page with API connection to partner sign-in, allowing drivers to opt into charging their customers for benefits

“As a user, I want to choose benefits that are most relevant to me so I only pay for coverage that I need.”

Feature: Benefit selection page with optionality to select one or more benefits

“As a user, I want to see that customer contributions are sufficient to cover my benefits so I know the program is working.”

Feature: Contribution summary chart on account page showing how much customer contributions covered the plan, how much the driver covered (if customer contributions don’t meet the cost of the monthly plan), and how much excess contributions the driver earned (if customer contributions exceed the cost of the monthly plan)

“As a user, I want the ability to withdraw excess customer contributions and put them in my bank account.”

Feature: Option to cash out funds to withdraw excess contributions to a bank account

“As a user, I want to have benefits in the event of unemployment to have peace of mind between gigs.”

Feature: Ability to indicate unemployment and continue receiving coverage up to 6 months post-gig at no extra cost, once enrolled in the program for 6 months

These stories were prioritized for their identification of basic user needs and their ability to differentiate our product offering in the marketplace.

Measuring Success

Our success metrics focus on three areas we would be most focused on as a new startup. 1) How well is our website converting visitors? 2) When subscribers use our site, are they getting value from it? 3) Are subscribers staying with us? Our tracked metrics are:

Website Conversion Rates

  • Homepage to benefits conversion rate
  • Completion of sign-up flow conversion rate

Subscriber Engagement Rates

  • Subscriber account page monthly active user count
  • Number of cash out requests of excess contributions

Subscription Retention Rates

  • Churn rate (measured across different time periods)

Looking Ahead

Our surveys revealed additional opportunities to continue pushing the envelope for gig workers’ benefits:

  1. As our user group is app-based drivers, we will need to quickly follow with a mobile application that allows for sign up and visibility into benefits.
  2. Given our interview with a DoorDash driver who only spoke Spanish, a Spanish translation option would be important in enabling Hispanic app-based drivers to have the same access to benefits.
  3. We found that app-based drivers also typically don’t have access to programs like unemployment benefits and worker’s compensation because they may not pay into state-funded programs. We would like to tackle the legal and regulatory landscape around this so that app-based drivers get the same opportunities as their full-time employee counterparts.
  4. In line with the previous goal, we’d love to expand our suite of benefits, including paid vacation and sick leave.

In conclusion, we believe Ensured can become the leader in facilitating app-based driver benefits, improving the quality of life for the estimated 3 million Americans who drive for the gig platforms we rely on.

Ensured earned 1st place at the April 2021 Project Jam Protothon organized by Product Buds. The theme for this product hackathon was Social Impact.

Team: Craig Parrish-FuenzalidaChristine ChenCherilyn SeethoCrystal Chan

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