Across HCM, that marketplace was consolidating: suites were growing by acquisition, and buyers were increasingly evaluating whole portfolios rather than individual products.

Much of that suite had arrived through acquisition. Each product worked, and each had been built by a team that knew it well — but they had been designed separately, and a customer moving from one to another could feel it. In 2024, Paycor’s leadership set out to make the portfolio work as a single experience rather than a collection of capabilities.

Addressing the Challenge

Despite having a talented internal team, the daily demands of building and maintaining products made it challenging to take a step back and holistically review the experience of the end user. “It was an opportune moment for us to enhance the experience of our prospect, especially with the integration of several new products into the Paycor ecosystem through M&A.” Anna Turner, then-Senior Vice President of Product, Commercialization, & User Experience at Paycor, explains. Within a year, that integration work would take on a different weight: Paycor itself would be the company acquired.

To gain fresh insights and a neutral perspective, Paycor engaged Sightglass to help clarify and enhance their portfolio.

A Collaborative Approach

Led by John Jarosz and Jessi O’Neill from Sightglass, the approach was to work closely with Paycor’s teams across various levels to understand their goals and pain points.

The inclusive approach involved not only the product and UX teams but also sales, customer experience, marketing and strategy partners. By facilitating workshops and conducting interviews, Sightglass harnessed the collective insights and creativity of the entire team. This collaborative process allowed Paycor to develop a customer-centric strategy that was rooted in their own ideas and expertise.

“Sightglass facilitated workshops that enabled us to tap into the collective ideas and expertise from various areas within our company,” explains Turner. “We appreciated that it wasn’t a one-size-fits all approach. The solutions emerged organically from our own team, empowering us to take ownership of the process.”

The workshops not only fostered alignment but also inspired new thinking. Paycor’s teams found themselves looking at their products with fresh eyes, inspired to imagine greater possibilities. As O’Neill explains, “Our goal was to show them what could be possible and how to break down the barriers—whether technological, organizational, or mindset-related—that prevented them from achieving that vision.”

The Outcome: A Clear and Inspiring Vision

Sightglass delivered the full experience architecture for the suite: cross-product blueprints showing how the portfolio should fit together, reference designs that visualized Paycor’s future experience across it, and final concept designs. An experience vision articulated new product principles and highlighted key opportunities, and an experience strategy set out the actionable steps to bring the vision to life, with Paycor’s roadmaps prioritized and aligned behind it.  These artifacts made the future potential of Paycor’s product ecosystem tangible and exciting. The market would soon put a value on that ecosystem.

Paycor had built a product organization to deliver features within each product line, which is where the day-to-day work sits in any B2B software company. Sightglass worked across those lines instead — a small, high-capability team operating like a scalpel — and handed back the answers that make 1+1=3. When the engagement ended, what was left was execution: the thing the organization had been designed to do in the first place.

“The final designs exceeded our expectations,” Turner describes. “Sightglass pushed us to think differently and stretch our vision. But the solutions were still ours, inspired by our ideas. They brought the expertise to elevate and articulate our strategy.”

Sightglass’s ability to distill complex problems, facilitate deep collaboration, and deliver actionable insights proved invaluable. By the end of the engagement, Paycor not only had a well-defined vision for its portfolio experience but also a reinvigorated team that felt ownership of the enhanced strategic direction. “Working with Sightglass was empowering and inspiring, enabling Paycor to achieve in a few weeks what would have taken months without their involvement,” says Turner.

What Happened Next

In January 2025, Paychex announced its agreement to acquire Paycor, completing the transaction that April at approximately $4.1 billion in enterprise value. The portfolio Paycor had worked to make coherent was the portfolio a buyer evaluated.

The speed mattered more than it appeared at the time. The vision, the architecture and the strategy were finished and in the organization’s hands in 2024 — months before the acquisition was announced, and while there was still time to act on them.

A suite that behaves like one product — data shared across it, workflows that run between products, and not simply more features inside each one — is what makes a group of acquisitions worth more than the sum of its parts. That cohesion contributed to a strong exit.

Paychex described the combined business as offering “the most comprehensive HCM portfolio in the industry.” The work of making a suite feel like one product does not end with an acquisition. It scales.