Calendly’s Top Lessons from 200+ Win-Loss Interviews

Question 1

Clozd: We’re excited to be here with Heather Pepe from Calendly. Heather, can you tell us a little bit about yourself?

Accepted Answer

Sure. I sit within product marketing at Calendly, and I lead our solutions and customer marketing teams. We're responsible for solutions, programs, and campaigns that target our key ICPs. That includes messaging and positioning. Also, we create collateral for our sales and CS teams. We also conduct market research through win-loss, through third-party site data, and through competitive intelligence. And then on the customer marketing side, we're really responsible for voice-of-the-customer and customer advocacy. That includes our customer stories, our testimonials, and our events.

Question 2

You've been running this win-loss program for almost three years now. What's changed from when you first took it over to where it is now?

Accepted Answer

When I started the program at Calendly, I did a listening tour with our sales, customer success, marketing, and product teams to really uncover what would be most valuable for them to hear from the win-loss program. As Calendly has evolved over the past three years … we've really adapted the program to those business changes. For instance, if we've had a change with our sales leadership, or we sunset a product, or we've had a shift in our company objectives, that's when we'll make changes to the program to adapt to those company changes. As we have new leaders and new stakeholders involved in the program, that's when I'll introduce it to them, get buy-in, and then we'll make changes to our interview guide, for instance, and maybe focus on a certain type of buyer or a certain product that will help us align better with Calendly's company objectives.

I've also been fortunate to have advocates on the executive team. I know that they're reading all the interviews as they come through, and our CRO, in particular, has been a big proponent of the program and getting buy-in from the rest of the executive team. At this point, we've run several programs with Clozd. We have our traditional win-loss program, and we've done over 200 interviews for that. And then we've also run an ICP-specific program, where we were targeting those key buyers. Most recently, we've been using the Flex Interviews—which are the async audio and video interviews—to really understand those buyers on the PLG side of the business.

Question 3

How do you get stakeholders involved, some of these other users, into the platform? What's been your best practice?

Accepted Answer

I think it's delivering the information to them in Slack, where a lot of us work in Calendly, and then getting buy-in from the leadership team. Recently, we added all of our sales team into Clozd. Previously, we only had managers and leadership in the program, so it's getting that buy-in from the leaders and then having that trickle down to the stakeholders within the org.

Question 4

That’s kind of a big change. Some of the companies we work with avoid giving salespeople access to the platform. Has it been a good change? Are they receptive to the feedback and the interviews?

Accepted Answer

Yes, very. I know when we did our readout last week to the sales and marketing teams, we had a lot of engagement from the reps on the call. They seem to find the insights very valuable and are using those learnings to improve their own sales process.

Question 5

Okay. Heather, you mentioned you've done over 200 interviews since you've taken over—in addition to the Flex Interviews. What are some of the themes and the trends that you're seeing, and how are you addressing those?

Accepted Answer

At Calendly, our voice-of-the-customer and qualitative data are so important, where now it's a company priority to really bring in that voice-of-the-customer data and feedback into every business decision. Direct customer feedback is so important for teams, like our sales and CS teams, where we can really understand where those challenges and blockers are. Then we can then make changes to our own processes to really improve the customer experience.

On the PLG side of the business, it's really understanding those challenges and blockers within that customer journey, and how we can make improvements to that first-time user experience.

We're also using the dashboards and tagging within Clozd to really view trends across a period of time and determine things like Decision Drivers that we're winning and losing deals to or competitors we're coming up against. Then we're reporting that information back to the company and also encouraging users to log into the Clozd Platform.

Question 6

There's obviously so much that goes into running a win-loss program—on top of all the other aspects of your role. How do you find time to share win-loss insights across the organization?

Accepted Answer

We have a dedicated win-loss Slack channel. The interviews populate as soon as they're published in real time, and we also conduct quarterly readouts. And for this quarter, we're actually trying something different. Right now we're doing roadshow-style presentations with specific departments, so smaller groups versus one large readout to create more engagement and collaboration. This gives everyone the opportunity to ask questions and talk about actionable next steps.

Question 7

It's been fun to watch your program grow and develop. I love how you've evolved over time. If you were talking to someone who’s new to win-loss analysis, what advice would you give them so they could build a successful program like Calendly does?

Accepted Answer

I would say first is executive sponsorship, really leaning into the executive who you'd get the most buy-in for the program. And then we can have that top-down approach, where they really socialize the value of it. And then I would say meet with all the stakeholders. Just do a listening tour, really figure out what would be most valuable for them to learn from this customer feedback and all the interviews. And then continue to communicate with those teams—whether it's Slack or email, wherever you meet—and really prove the value of the program that way, by providing that feedback loop and that actionable data back to those teams.

Question 8

If you were going to start and try to get buy-in from one group, who would you suggest?

Accepted Answer

I'd say for sales, the CRO. At Calendly, we have a chief customer officer who runs our CS and CX teams. I would say to just find a leader who's really passionate about voice-of-the-customer and that qualitative feedback.

As far as getting buy-in, I would say creating a business case or a one-pager and really thinking through the strategy for the program and how it will provide value and benefits back to the business. Once you justify that, it's a matter of trying it out and then looking at those actionable insights and seeing what value it provides back to the team. That's how you can start. As I mentioned, our program has evolved, and you can continue evolving and adapting yours to your business needs.

Calendly’s Top Lessons from 200+ Win-Loss Interviews

Calendly’s top lessons learned from 200+ win-loss interviews

Heather Pepe

Senior Manager, Solutions Marketing at Calendly

Q&A