Calendly

When Calendly invited me to their annual Kickoff, I didn't hesitate. Five years as a customer. Five years of never once looking at an alternative. That kind of loyalty doesn't come from a product alone. It comes from a company that actually listens. I was part of a customer panel in front of their entire team. Not to celebrate the wins—to share the real picture. The gaps. The friction. The honest "here's what isn't working" that most companies claim they want but rarely create space for. And here's what struck me: It wasn't just leadership listening. It was everyone. The engineers. The product team. The people building the thing every day. They were leaning in—taking notes, asking questions, connecting what I shared to the work happening behind the scenes. That kind of engagement is rare. And as someone who advises leadership teams for a living, I don't say that lightly. Then Monday morning I got back to my desk. An email was waiting. They'd added me to a working group for ongoing customer feedback. That's the follow-through that separates good companies from great ones. People want to do meaningful work. But the culture has to create the conditions for it. I wrote about what this experience taught me about customer focus, sales, and leadership in my latest blog. Link in comments. And in my Substack next week I'm going deeper—what it looks like when the whole team is connected to the customer, not just the people at the top, and why that's the difference between companies that scale and companies that stall. Both links in comments. Thank you to the Calendly team, Tope Awotona, Shane Murphy-Reuter, Thomas Melrose, MBA, Larry Cloud, Shiv Shankar, Chelsea Fletcher and Greg Rokisky for building something worth celebrating. And to my fellow panelists Melissa Mittelstaedt and Olivia Hutto August—grateful to have shared that stage with you.

What do you get when you mix the desert, 2026 planning and hundreds of employees? Calendly Kickoff 2026 🌵💙 We heard from customers like Amirah, Olivia and Melissa who run their own businesses and juggle managing everything themselves. They talked about what's hard right now, what they're building toward and how they're trying to grow without burning out. Bill Carr, who helped build some of Amazon's biggest wins, walked us through what it actually means to work backwards from what customers need. Our leadership showed us what's on the path ahead. And we tested new features and asked a lot of questions about whether we're solving the right problems. What stuck with us: the customers we build for are juggling impossible workloads. They're trying to do great work for their clients while also running every other part of their business. Every hour matters. Every decision about where to spend their time is high stakes. We left Tucson clearer on what we're building and why it matters. Let's go Team Calendly (and that includes you) 🤘

When Calendly invited me to their Kickoff event, the only option was "YES!" I've been a Calendly customer since October 26, 2020, and I've never even considered a different scheduling tool. When something works (and makes your business run seamlessly), you use it. Over a year ago, they invited me to join their research community. "A chance to give my feedback without getting irritated glances?!" Yes please. Not only did they forego irritated glances, but they also encouraged me to find what wasn't working. Figure out the gaps. Identify pain points. They wanted the dirt. "Have I found my calling?" Feedback Giver Extraordinaire. I'll work on getting a name plate for that & get back to you. The purpose of having customers at the Calendly Kickoff event was to give the entire company a glimpse into our daily lives. They wanted to understand what it looks like for small business owners juggling all the plates: marketing, business development, finances, client interactions, scheduling, social media creation... to name a few. The customer panel featured three of us: Olivia Hutto August, Amirah Raveneau-Bey, and yours truly. The panel host was the Go-To-Market President, Shane Murphy-Reuter. Thank you, Shane, for making the session fun & comfortable. We laughed, shared, answered questions, and connected with the Calendly team. The energy of appreciation and kindness radiated from the audience to the stage and from the stage back to the audience. One word to describe it... magical. The following day, we had a lot of fun recording with Calendly's social media manager, Greg Rokisky (more to come later), and had the pleasure of meeting with various teams for a deeper dive into the products and a bit about what's forthcoming. Do not try to bribe me for info... my lips are sealed! 🤐 AND... a huge shout out to Thomas Melrose, MBA & Larry Cloud for all the work you did to ensure our trip was super smooth. You are rockstars! 🤘 I left there with new friends, lots of memories, and an even greater appreciation for Calendly. Thank you for centering your customer's experience in everything you do. You don't just talk the talk, you walk the walk. [Photo Descriptions. One: Melissa is sitting in a beige armchair on stage. Two: A collage of pictures... Melissa holding up a Calendly Kickoff badge, the Calendly logo projected on a hillside, and a cookie decorated with the Calendly logo. Three: Shane, Amirah, Melissa, and Olivia standing in front of the big screen that displays "Calendly Kickoff 2026." Four: A picture from the back of the audience onto the stage. Five: A selfie of 12 people, Melissa + Scheduling Team, in a conference room. Six: A landscape photo of 16 people, Melissa & Amirah + Notetaker Team, in a conference room. Seven: Melissa sitting on a couch with Calendly pillows, smiling, with this message above: Calendly, I cannot thank you enough. Thank you for listening. Thank you for learning. Thank you for caring.]