March 31, 2022

Patrick Moran, Calendly CMO

One of the perks of “crashing and burning” at the very start of your career, as the now CMO of Calendly Patrick Moran realised the hard way, is that the only way is up.
Patrick Moran, Calendly CMO

As a teenager growing up in Boston, Moran loved music and was both an emcee and part of a hip hop band called 36 – he spookily lived at three number 36s as a child – for which he played guitar and drums. Once school was over, he decided to launch a recording studio, all the while studying audio engineering and communications at his local Emerson College.

“It was such an exciting time because music had just moved from analogue to digital, so instead of cutting tapes with a razor blade, you could start editing music on a screen,” Moran recalls over Zoom. But the studio – where Moran, unable to afford rent, was also living – went broke, leaving the young entrepreneur $300,000 in debt.

But his experience was not for nothing. “It had forced me to learn how to market bands, how to get booked, how to get fans. Essentially I was learning the ropes of marketing.” And so Moran launched online utilities marketplace age 25, which allowed customers to access their bills through the internet for the first time, and became its head of marketing.

“We had raised $90 million, had become the largest VC fundraised startup on the east coast,” says Moran, who was able to pay off his recording studio debts. “But while we grew really quickly, we then crashed and burned really quickly. We filed to go public, so somewhere in this house I have this leather bound book in a box that says that I'm worth millions upon millions of dollars. But, in reality, I walked away with nothing.”

Since these formative years in his early twenties however, success for Moran has been relentless, with marketing roles across companies such as Fuze Box, New Relic and Quip, sitting on advisory boards for Optimizely, Robocorp and Coda. He joined Atlanta-based unicorn Calendly – the cloud-based scheduling platform which counts over 10m users and is valued at $3b – as Chief Revenue Officer in 2020, before being promoted to CMO late last year.

With such a breadth of experience, and first-hand experience of meaningful failure, Moran has learned indispensable lessons on how to successfully launch and market a startup. What are his biggest learnings to date?

“The fundamental is, to be really honest about the business model. With, the phone monopolies resold their networks to us, but we only had 20 per cent margins, and so we had to acquire the customer, service the customer, and deliver value to the customer, all on these really thin margins. We thought the internet would change everything and we'd be able to service all these customers online rather than in call centers. But actually, people still wanted the phone calls. The math didn’t work. We were too starry eyed.”

“Second of all,” Moran adds, “make yourself visible. I was successful at the companies I worked at because I wasn’t afraid to speak up in meetings, I wasn't afraid to ask the CEO for a half hour of their time, I wasn't afraid to put out a provocative email that made us think differently.”

“And thirdly, learn to hire. When I was at New Relic I was one of the first 20 employees. But five years later there were 95 of us in the marketing team. And what I learned to hire for was grit – the drive to make something happen – and what I call “framework thinking”, which is the ability to pattern match across problems. It is so valuable when it comes to problem solving.”

“And finally, taking risks,” concludes Moran, referencing how Calendly’s origin story is one built on risk – its founder, Tope Awotona, cashed in his 401k retirement fund and went into debt to launch the business, which raised $350m last January in a Series B.

“On a more personal level, joining Calendly as CRO was a massive risk for me,” he continues. “I had never run a sales organisation, which I think was what Calendly wanted. They wanted someone who would be empathetic to the customer, who wasn't aggressive and wasn’t going to change the culture. But man it was anxiety inducing!”

Calendly’s growth model, too, was risky: “trusting that one Calendly user would tell another, and it would scale that way”, says Moran. “But it all comes down to that end user love. With every big enterprise we bring on, they already have 1000 employees using Calendly. To this day, we’ve never sold top-down to a CIO who wasn’t responding to the fact that their employees love it. So the risk was betting on enterprise sales and building up that team without enough proof points that it would work. But it did.”

Calendly’s growth accelerated over the pandemic, as more workers needed to book in meetings to offset remote work. This period of change was also what prompted Calendly to ditch its office space for an all-remote workforce in July last year. This is in addition to their “Best in Breed” approach to talent, by which Calendly uses agencies for services they are better equipped for than Calendly to execute such as media buying or online advertising, and hires contractors for certain projects such as, most recently, an SEO audit.

So with a scattered workforce, how does Moran keep all his colleagues feeling part of the same mission?

“We have two to three events a year where we’ll bring every single employee to some great destination, so that we can connect as humans rather than co-workers,” he says.

And what about remote get-togethers on a more regular basis?

“We will have cocktail hours remotely, and then we will have Zoom calls where literally 400 people are on the call. It sounds unwieldy, particularly since nobody stays on mute, but it’s great because when someone gets promoted you can hear everyone hollering and clapping. It’s a pandemonium, but it’s also pretty darn motivating and exciting. And that’s often the example I will give people when describing the Calendly culture.” Moran’s voice is hoarse. “I was on one of these Zooms last night, as you can tell!”

Of course, creating a motivating company culture is not as easy as Moran makes it sound. And where does a company culture come from in the first place?

“It starts with the CEO, with Tope,” says Moran. Not all CEOs are like that, agrees Moran, as “many of them feel abstract, a figure that is not connectable”. But at Calendly, “Tope was actively involved in hiring his first 100 people, and he chose those people on a cultural fit. And then by investing in those first 100 relationships personally, he allowed them to feel comfortable.”

This culture is reflected in the way Calendly talks to its customers: full of heart emojis and conversational tweets. That might be why, Moran says, a recent bit of viral bad press ended up working in Calendly’s favour. After a Twitter user complained that Calendly etiquette was a “naked display of social capital dynamics” because it suggested that those who used it thought their time was more important than those they were meeting with (since the platform offers gaps in their schedule for the other person to choose from). Calendly users jumped to defend the platform, and the company saw a spike in sign-ups. And, far from blocking its ears, Calendly then proactively provided its users with an etiquette guide. “Calendly’s core value is respect, and I think our customers know that because of the way we talk to them,” explains Moran, simply.

Finally, as Calendly looks forward to more growth, and the working landscape continues to evolve, what does “the future of work” look like, for Moran?

Moran sounds excited by the challenge. “Our most finite resource is time. So I think everyone is going to start talking about the time economy. And not just about saving time, but maximising the potential of your time. And, while there are many conversations about the metaverse and so on, the one constant, unfortunately, is that you cannot clone yourself and be in both places at once. We are still going to be straddling time between one world and another.” Moran smiles. “And you know, hopefully, Calendly will be able to help with that."


Hire someone if


“They can answer the question: ‘When was a situation when you had to create something from new?’ I always look for the answer that shows someone has built something from literally ground zero rather than incrementally.”

Productivity hack


“Besides Calendly of course, it has to be Asana, the task management app. If you need a piece of digital content created, you fill out a form in Asana and it creates three tickets for all the people that need to be involved in it. And so we don’t need an engineer involved to build those workflows.”

On my bedside table


“The Messy Middle by Scott Belsky, which talks about the chaos of creating something new, and The Power of Now by Eckhart Tolle, about living in the present.”

Marketing mantra


“Start with the end user. You may have grand aims of selling your business, without actually thinking about whether customers are actually using your product. You want your customers to think, ‘I dare you to try and take this away from me’.”

Written by
Eleanor Halls

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