Calendly worked with Clozd to meticulously build out their win-loss program, and over the last two years—and more than 150 interviews—that program has reliably delivered valuable insights to teams throughout their organization. From the outset, Calendly’s primary objectives were to learn how they could improve their win rate, build a sustainable competitive advantage, and uncover the exact reasons why they were winning and losing deals. Having a clear direction—and then multiple user-friendly channels to distribute the insights from their win-loss interviews—has helped Calendly’s program thrive.

Kicking off their win-loss program

Heather Pepe, Calendly’s senior manager of solutions marketing, understands the value a win-loss analysis program can bring—both to her marketing team as well as to the company as a whole.

“Win-loss has always been really impactful as a marketer, because it helps us better understand our target market and their buying behaviors,” she said. “We also want to make sure those cross-functional stakeholders find the intel valuable and actionable to shape new strategies and help us meet our company goals.”

Setting up an impactful win-loss program, however, is an intentional process that requires collaboration and dedicated resources. Pepe partnered with Clozd and went to great lengths to establish clear expectations and engage stakeholders throughout her organization.

“Prior to launching the program, I held meetings with the leaders from our product, marketing, sales, and customer success teams,” Pepe said. “And then we reviewed the scope of the project, the process of approving the prospects and customers we would interview, the expectation on the program results, and the deliverables we would receive from the Clozd team. It really didn't take much convincing for others to see the value of the program.”

Through these meetings, Calendly’s team developed a detailed plan of what they wanted to get from their win-loss program.

Having a clear direction from the outset helped her build cross-functional buy-in, which is an important step toward creating a program that produces actionable insights.

As the program has matured, Pepe has worked to foster a collaborative culture around win-loss analysis. She frequently shares documentation—including the program overview, results, and all past reports—with her team, and she maintains alignment around what problems they're trying to solve and the benefits they can achieve. 

Because of this, Calendly’s partnership with Clozd delivers value throughout their organization. Direct customer feedback helps their product team hone their product strategy, while their sales and CS teams use win-loss data to improve their sales process and customer onboarding experience. 

“And for the marketing team in particular, I've found it helpful to provide a demo of the platform, since it provides so many valuable insights to better understand our total addressable market, and the sales-led growth side of the business,” Pepe said.‍

Targeting high-value customers

Once her team got their win-loss program up and running smoothly, however, Pepe didn’t simply set it on autopilot. 

“For the traditional win-loss program, we continue to assess our interview guide and outreach emails to ensure that we're reaching the key contacts who we want to learn from,” she said. “We also want to make sure the questions we're asking during the interview will provide answers that drive the most impact for Calendly.”

Thanks to that continual analysis, Calendly now runs two different win-loss programs within Clozd’s platform—one for traditional customers and prospects, and another that focuses on the full buyer journey of Calendly’s core ICPs. Calendly’s team customized their additional program by creating a new interview guide and new outreach emails. They also hand-selected the customers and prospects who meet specific criteria within certain roles, departments, company sizes, and more. 

The objective of their custom program is to better understand the challenges their core customers are facing—as well as how they’d like to use Calendly to solve their business problems.

Delivering impactful insights

Pepe’s efforts have created stickiness around Calendly’s win-loss program. 

“There’s been high engagement from our team,” she said. “I have a lot of leaders and team managers reach out to me to involve some of their team members in the program, so it's definitely gathered a lot of traction.”

Clozd has completed more than 150 interviews with Calendly’s prospects and customers, and Calendly’s high level of adoption and engagement relate directly to how those insights have been delivered. Once an interview is complete and available in the Clozd Platform, Calendly’s team is notified via Slack and email.

“I love the Slack integration,” Pepe said. “We have a Slack group dedicated to win-loss. As the interviews are added to the platform, they come through Slack and email in real-time. And then those in that program can link directly to the full interviews from Slack and also access the dashboard in Clozd which shows our win rate, the top wins and losses, the top reasons we're winning and losing, and all the interviews that were recently posted.

Additionally, Clozd hosts a readout each quarter where the program manager delivers the client’s win-loss analysis report—including an executive summary, key takeaways, Decision Driver analysis, competitor analysis, and more.

“I’d say the most visible place that leaders and stakeholders receive program findings are through the readouts,” Pepe said. “We get a lot of our C-level executives on the report readouts we do every quarter. In working with the Clozd team for so long, we've been able to customize those quarterly reports, so they're even more relevant and useful for the Calendly audience. The leaders and stakeholders within our sales, customer success, marketing, and product teams are encouraged to attend those readouts and ask any questions. And then as new people join Calendly, they can access the previous reports and meeting recordings on the platform.”