Guideline's Path to Product-Market Fit — The Early Decisions That Powered Its Acquisition by Gusto

Ten years after shaking up the retirement fund industry for SMBs, Guideline has been acquired by Gusto. Here, co-founder Kevin Busque shares the early-stage decisions and pivots that put the startup on the path to success.

It’s 2014 and Kevin Busque is too busy to be verifying 401(k) contributions on every pay period. As co-founder and VP of Technology of TaskRabbit, he is focused on scaling the company rapidly. TaskRabbit launched in London, its first international market, and its headcount has grown to 70.

Compared to his days as a scrappy early-stage founder, Busque spends a lot of time thinking about leadership, hiring, HR, and employee benefits. It’s the latter in particular that begins to keep him up at night, after he discovers that only 36% of TaskRabbit employees are enrolled in the company’s 401(k) plan.

“I remember the number, because when I found out, I was flabbergasted,” Busque recalls.

He begins trying to understand why so few of his employees are making use of this company benefit, which costs TaskRabbit more than $20,000 annually. As he takes a closer look at their 401(k) providers, he starts to grasp the issues: clunky systems, a lack of integrations, and confusing fee structures. His founder’s brain is itching, seeing the problem as a challenge. He becomes obsessed with solving it.

Retirement funds for SMBs might not seem like a sexy market sector, but one that was begging for someone to come and shake it up.

Cut to August 2025. Guideline, the billion-dollar company Busque co-founded with fellow TaskRabbit alums Jeremy Caballero and Mike Nelson in 2015 to make 401(k) simple for SMBs, enters a deal to be acquired by HR tech giant Gusto. Busque describes it not as an ending for Guideline, but the beginning of a new chapter.

When traditional providers ignored SMBs, Busque noticed the gap — and the opportunity

When Busque sees that 36% figure, he begins examining their benefits program and finds inefficiencies.

“At TaskRabbit, our payroll and our 401(k) weren't integrated, even though they came from the same company. That was mind blowing to me.”

Then there were the fees:

“In the 401(k) legacy ecosystem, there are middlemen that charge asset-based fees: your record keeper, your TPA, your fund investment manager. The pricing is incredibly opaque.”

Busque began searching for an alternative to TaskRabbit’s 401(k) provider.

“Fidelity didn't want to talk to TaskRabbit,” he says. “We had 70 employees and zero assets.”

Many founders will recognize the terrain Busque describes. It was clear to him that SMBs were in desperate need of an accessible, affordable, modernized solution for retirement funds, especially 401(k).

While still at TaskRabbit, Busque spent almost two years doing in-depth analysis of retirement fund fees and regulations, realizing that if he wanted to solve the major flaws in 401(k) offerings, he’d need to build an extremely complex product from scratch.

The product decisions that gave Guideline its edge

Busque approached Nelson and Caballero and told them about the idea. He made the call to leave TaskRabbit and focus on his new project full-time.

“I knew I was going to do something different at some point,” he says.

His first priority? Fundraising.

The co-founders began trying to raise their seed round. To prove their idea, they built a tool that estimated fees individuals were paying out of their 401(k).

“Seeing the potential investors’ eyes widen at how fees were eroding retirement savings affirmed Busque’s belief that Guideline had strong potential for product-market fit.”

Early on in the fundraising process, Busque was pitching a product that was more encompassing than just 401(k). But one VC advised them to focus on one thing. Busque took this seriously, leading to a pivotal narrowing of focus.

Guideline launched at 0% AUM (assets under management). “People couldn't believe we could do something like that,” he says.

Another example is Guideline’s approach to enrollment. Busque believes that auto-enrollment is vital. Instead of requiring employees to opt-in to the 401(k), they are automatically enrolled but can opt-out easily.

“Automatic enrollment was one of the earliest decisions we made.”

Busque emphasizes the importance of relentless focus on participant outcome: “Stay true to who you are.”

How a payroll integration with Gusto helped scale Guideline to tens of thousands of SMB customers

After the “failure” of their outbound sales efforts, Busque reached out to Gusto. Together, they built an integration that allowed Guideline to tap Gusto’s customer base.

“We built this whole ecosystem with them, and they became a customer. The integration gave us operational excellence and scale.”

A decade of partnership becomes an acquisition

The possibility of Gusto acquiring Guideline was discussed since 2016. Talk became serious in the spring of 2024.

The acquisition process was complicated due to Guideline being structured as multiple licensed and regulated entities.

Busque’s long-time rapport with his outside counsel was crucial throughout the process.

“Be careful who you choose for the professionals around the table. Make sure you have a solid relationship with them.”

For Busque, the acquisition means the mission he began building Guideline with — to fix 401(k) for SMBs — can continue to scale. He believes it sets up a better experience for a new generation of investors.

“Gen Z is one of the fastest growing investing categories. We can do that as one team under Gusto.