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How Zenefits increased their win rate by 3-5x using Gong

Coaching Deal Execution Strategic Initiatives Small Business North America Software
increase in early stage conversion
higher win rates

The challenge

Zenefits wasn’t sure why their early stage conversions fell off after the demo stage. They needed better information to help them understand where to focus their efforts so they could improve reps’ early conversion and win rates.

The outcome

Gong’s customized deal boards helped the leadership team uncover troubled areas on a macro level, and its insights helped the sales team drill down on a micro level to support deals in play. This resulted in increases to win rates and early stage conversions, and a new methodology that has their revenue team running like clockwork.


San Francisco, CA



Company size



Enterprise Software & Network Solutions

Gong’s deal boards gave us visibility into so many opportunities.
Aileen Cowles
Director of Sales @ Zenefits

Reveal layers of insights

Zenefits is a cloud-based SaaS tool for HR teams, with a focus on payroll and insurance. Like most sales orgs, the company’s sales cycle is parsed out in stages. The sales team wanted to dig deeper into their data to uncover opportunities they might be missing at both a macro and a micro level.

“We wanted to peel back the onion and find out where we could really improve,” says Director of Sales, Aileen Cowles. She and her team were most focused on the early stages of their sales cycle.

The information they uncovered improved their early stage conversion rate and their win rate with just one tool.

Macro: Customize dashboards so it’s never “too late”

In sales, looking backwards can be educational, but it won’t help you with the deal you already lost. Cowles and her team needed a way to get visibility mid-deal so they could turn insights into action right away. 

“You’re doing a deal review or you’re at a forecasting meeting, and you end up talking about the woulda, shoulda, coulda,” she says. “It always just seems too late. One of our main areas of focus is finding early indicators and ways to really impact and influence a deal mid-flight.”

They used Gong’s deal board to give senior leadership a macro-level view of their pipeline, which resulted in the decision to aim for better conversion rates. The data showed that, despite many opportunities available in stage two, prospects weren’t converting at a reasonable rate. Something was missing. 

Zenefits was able to tailor Gong’s deal board and deal insights, and focus exclusively on its unique team and company goals.

Micro: Solve issues right down to the rep

Once this core issue was uncovered using Gong’s deal board, Cowles was able to use deal insights to drill down and understand what impeded conversions. Focusing on one area at a time allowed her to highlight and solve problems as quickly as possible. 

“We found that having fewer areas of focus helped us align our planning and processes and keep them connected to our goals, even at the rep level,” says Cowles. 

One point of focus for Zenefits was contact numbers. “As we looked through these segments, we found that our win rates were higher when we engaged with more contacts.” Their win rates weren’t just a little bit higher, but three to five times higher. This knowledge changed everything and helps flip mid-deal question marks into turning points.

“Gong serves as a warning tool. We’re able to understand the segment size of who we’re speaking with and how many contacts are involved in the deal,” says Cowles. “That’s how we were able to narrow it down to the micro level.”

With this data, the team’s strategic conversations have become more organic. They’re able to ask important questions: 

  • How can we build this information into our process? 
  • Is every deal multithreaded? 

“Not only were we able to create opportunities, we could set reps up for success by asking how many people were involved in each deal,” says Cowles. “That was really eye-opening for us.”

A holistic view: Use a common language to improve your team

Using these tools — on top of their 3-5x higher win rates — Zenefits was also able to increase their early stage conversion by 20%. Having direct access to KPIs in Gong made tracking progress even easier. 

Using Gong across the company allowed Cowles and her colleagues to implement a standard methodology that made strategizing easier. “We’re now able to have a standard language and methodology across the board so we can work better together when people from different teams talk about deals and forecasting.” 

This shared knowledge and understanding also resulted in increased team selling, with execs jumping on calls and teammates supporting each other. “Team selling provides a better client experience and increases win rates,” says Cowles. 

This knowledge also carries over into forecast meetings and one-on-ones. Features like inline editing make a huge difference when teams share data up and down the ladder. “If you do it week over week, it becomes natural,” says Cowles. “My reps rave about it every single time.”

Personalized insights provide an incredible level of connection across teams. They can turn “how can we improve” and “what are we missing” into “here are the proven steps to success”. Enabling everyone, from leadership to reps, to access the information they need to hit their targets is why Gong has become Cowles’s favorite tool in her arsenal. 

“Gong is the third tab I open each day after my email and calendar,” she says. “Two years ago, when I first started using Gong, I was excited to see what it could do. Now I move straight into getting the data and turning it into action.”

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