Case Study: How Pebble Helped Mystery Grow

Discover how by switching to Pebble, Mystery was able to offer its employees better health benefits at a lower price, while also growing the team by 50%.

Mystery is an HR tech startup based in the Seattle area. Founded in 2019, this fresh company provides data analytics to help businesses understand their employee engagement and create connections between their remote or hybrid work teams. They’ve raised $20M to make it happen.

With a team that spans over 17 states, Mystery is passionate about getting the most out of a remote work environment. This includes offering its employees affordable healthcare. 

Unfortunately, this is easier said than done. As Mystery’s team began to expand outside of Washington state, company leaders found it increasingly difficult to provide the high level of healthcare they believed their employees deserved. That is until they partnered with Pebble. 

We sat down with Jackie Wagner, former chief of staff at Mystery, to discuss what Mystery’s experience with health insurance was like both before and after signing up with Pebble.

  • Growing Pains for a Distributed Company
  • What Pebble Brought to the Table
  • How Pebble Has Helped So Far
  • Discover How Pebble Can Take the Guesswork Out of Healthcare

Growing Pains for a Distributed Company

Mystery’s homepage.

Like many startups, Mystery originally offered health insurance through its payroll platform. Signing up was easy, and it was one less thing for the founders to worry about as they focused on growing their business.  

“Although it was easy to use, the insurance wasn’t great cost benefit-wise. We’d often receive complaints from employees outside of Washington — especially those on the East Coast. They were in a lot of pain,” Jackie explains.

Jackie joined Mystery in 2021 as the chief of staff. During her time at the company, she saw the team grow from a close-knit group of about 15 in the Seattle area to 60 employees across the  U.S.

While Mystery’s existing coverage wasn’t too expensive, benefits were limited, particularly for employees living outside of Washington state. This hadn’t been a problem when most of Mystery’s staff were in Seattle. However, as the team grew on the East Coast, the limited benefits and network options started to become an issue. 

Healthcare benefits can be confusing for startups, especially if teams are spread out.‍

The real wake-up call came when Jackie learned of an employee living in NYC who couldn’t find an in-network doctor anywhere near them.

“I specifically remember someone saying to me, ‘There is no doctor in-network on our entire insurance plan within 20 miles. I live in New York City. How is that possible?’ She needed to go to urgent care, and she ended up finding one that took her insurance, but it was an hour away.”

In addition to network issues on the East Coast, Mystery had no contributions towards dependent care with its previous insurance provider. This was also a growing issue for the company. 

Not only would offering dependent coverage and fixing network issues please current employees, but that would also make Mystery more attractive and competitive when expanding its team in the future.  

After all, the 2022 SHRM Employee Benefits Survey found that 88% of respondents consider health benefits to be the most important benefits a business can offer employees. 

The team at Mystery knew the time had come to make a change, but where to begin? How could they guarantee they were picking the right plan for employees without falling into the common traps so often experienced by small businesses when choosing health insurance? 

What Pebble Brought to the Table

Not only did Pebble bring Mystery a proposal, but the team also took the time to answer questions and work out issues together. 

Although they weren’t thrilled with their current coverage, Mystery’s team wasn’t actively looking for a new health insurance provider. They initially thought expanding their coverage would be enough.

However, their existing broker took forever to return phone calls or emails. Mystery would ask for a quote, wait a week, receive a complicated answer, then ask more questions and wait another week for a response. It was a slow and frustrating process.

“I heard about (Pebble) through one of the founders. He told me I should check it out. I was so impressed with their product and how they made it easy to understand as I was evaluating new benefits. It just felt like a no-brainer to move forward with them,” Jackie says.

When the team reached out to Pebble, they received answers quickly — often the same day. They also liked how Pebble explained things concretely (without resorting to jargon) and with lots of examples, so everyone could understand the plan details.

Pebble helped Mystery cut its healthcare costs while adding attractive benefits like a $0 deductible and 50% dependent coverage. The company doubled in size while Jackie was there, and she’s sure the competitive healthcare plan attracted great candidates to the team.

“Pebble made it so that insurance wasn't even a worry. Made it so simple. I was expecting to have to become an expert, and I didn't have to, which was one of my favorite things.”

Instead of adding more work, switching providers was far easier in the long run.

How Pebble Has Helped So Far

Mystery now has a better benefits plan that offers dependent care and covers everyone regardless of location.

Mystery thinks of Pebble as “insurance for real people.”

One of the team’s favorite parts about working with Pebble is how the benefits provider invested a lot of time in answering staff members’ questions — via phone, email, and Pebble’s app — and made them feel supported.

“The consistency of excellence was just incredible. And it was something that, as a startup operator, was something that impressed me and was something I wanted to strive for in my day-to-day as well,” Jackie adds.

Pebble came in with the goal of building a benefits plan that would work for Mystery’s entire team, whether they were in Washington state, Florida, or anywhere in between.

Pebble created an easy-to-understand benefits guide that included both health benefits and other indirect compensation benefits, like a 401(k) plan and health reimbursement arrangement (HRA) options for team members. The guide was so helpful that hiring managers started including it with their offer letters. 

Since Pebble was also a venture-backed startup, the team understood Mystery’s unique position and could address the problems head-on. 

They also took care of the open enrollment process and transition for Mystery, which allowed the management team to focus their energy on other aspects of the business.

The benefits provider’s dedicated customer support team was available to assist Mystery with any questions company leaders or employees had about their new insurance plan. Employees could message, call or email Pebble with questions about their coverage rather than having to reach out to the insurance company.

Pebble even helped Mystery understand its options with post-employment care programs like COBRA. In short, Pebble has made it easier for Mystery to offer competitive benefits and stay fully compliant as it grows. 

Discover How Pebble Can Take the Guesswork Out of Healthcare  

Overall, Mystery has had a great experience with Pebble. It now has employees in over 17 states and can offer comprehensive benefits to all of them.

While Jackie’s no longer with the company, she was so impressed with Pebble that she even talks about introducing them at her own startup. 

“I genuinely recommend Pebble to founders and chiefs of staff all the time. Their value is just incredible,” she says.

Meanwhile, Mystery’s employees continue to enjoy a $0 deductible plan, dependent care, and HRA options. All for a price they can afford on a plan they can understand.

Wondering why Mystery was so impressed? Reach out to Pebble today, and we’ll work with you to see how you can offer amazing benefits.