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Professional Development

Tim Da'Graca shares his story of how he grew his career at Calendly

While in high school, Tim DaGraca worked as a Nielsen movie researcher in the mall. During that time, Tim built up his resilience to rejection and discovered different ways to strategically engage in conversations so mall-goers would be willing to stop and watch unreleased trailers. The job might seem odd for a high school student, but for Tim, he felt at home.

For the next ten years, Tim continued working with customers in various capacities—everything from a freelance video producer to a technical specialist at Apple. Little did he know, his retail and creative experiences would ultimately prepare him for a growing career in customer experience and, now, product at Calendly.

Customer Experience at Calendly

In early 2017, Tim came across a Customer Happiness Specialist job opening at Calendly and applied for the role. “At the time, I couldn’t even pronounce the company name but I figured, ‘I’m a happy guy and can work with customers,’ and self-checked myself against the job requirements. But what really sold me was seeing photos of all of their happy people on their Glassdoor company profile. They were laughing while stretched out on colorful bean bags, traveling together in the summer sun, and just smiling from ear to ear wherever they were, with whatever they were doing. And the best part about that was, one month later, I was doing the same thing.”

From the work to the people on the team, Tim loved the Customer Experience department. At the same time, Tim knew he wanted to continue building his skills further, and that meant exploring new opportunities that would support his professional goals. “I saw myself on the Customer Experience ‘trampoline,’ just bouncing until I was ready to bounce out (pun intended) and join another department, or leave Calendly altogether.”

But Tim knew he didn’t want to leave Calendly. “Our people are too great. Our product is phenomenal, and there are so many great perks that, (cue: Chingy’s ‘Pullin’ Me Back’) ‘everytime I try to leave something keeps pulling me back… it was meant to be, it was meant for me, so that means we gotta make it work.”

Goodbye Customer Experience, Hello Product

And sure enough, Tim did make it work. “After three years in CX and cementing myself as a leader, product trainer, and close collaborator with the Product Content Strategy team, I finally gained the mindset, visibility, and skillset that would help launch me into my new role. Deep down, I always knew that my entry into another department wouldn’t be anywhere else, but rather with the company, product, and people I love.”

The transition from CX to Product wasn’t an easy one, though. But thankfully, Tim had support from his manager and team. Reflecting on his earlier days at Calendly, Tim realized he was spreading himself too thin, taking on too much additional work on top of his normal job responsibilities. This left Tim with very little time to focus on his professional growth.

“Luckily, I had leaders who were gracious enough to help me divvy up my duties or projects if needed. And that’s one of the best things about Calendly -- it’s not just your leaders that are there for you but your team members as well. ‘Starting with Human’ is one of the most important core values we exhibit on a daily basis, and understanding others and sharing the workload is how we all win.”

While Tim knew he didn’t want to be in Customer Experience forever, he also didn’t have a concrete plan on where he wanted to go next. He was grateful to his former manager for working with him to figure out his next steps.

“It was a little after my second year anniversary at Calendly. I’ll never forget this time because I was a new dad coming back from parental leave who wanted even more out of his career, so I ended up having a one-on-one meeting with my manager. She encouraged me to write down my general interests around the key areas I was interested in at Calendly. At the time, we were also piloting some changes in CX around product education so I stepped up to be the company’s trainer since it aligned with my interests and passion for people. We went over my list one-by-one and defined a plan, what the KPIs were, and how we could start leveraging my skills and interests to see some career movement either into a new role in CX or another department.”

Knowing where he wanted to go, Tim began making strategic decisions to help him transition to a content role, whether that was on the CX or Product team. When Calendly’s content manager was moving on from her role, Tim saw it as an opportunity to get his foot in the door and met with her to see how he could support the team in the interim.

“That meeting led me to writing a few articles on new feature releases and making updates to existing ones. When we hired our Head of Product Content Strategy in fall of 2019, I kept collaborating with the content team from a distance as an editor and knowledge resource. By this time, I had spent a lot of time training new hires on the product—so I knew it—and wanted to embed myself more in the content strategy process. In January 2020, I set up a meeting to pitch in a little more and see if I could move the needle on my career growth.” That meeting ultimately led Tim to a new content specialist role on the Product team.

Making the Leap

Making a career change isn’t always easy, as there’s no one-size-fits-all approach that works for everyone. For Tim, it was his strong belief in helping others and his persistence in pursuing his passion for content creation that helped turn a vision into reality.

“The best advice I can give, and one thing to live by, is to serve others. It’s one of the hardest things to do, but something I remind myself of frequently to help me with servitude is from John C. Maxwell’s book Be a People Person. It’s, ‘People don’t care how much you know until they know how much you care.’ Let that resonate. Before you try to get people to serve you by impressing them with your immense amount of knowledge, learn to Start with Human and care about them and their needs first.”

And don’t forget to pause and enjoy the journey you’re taking, as challenging as it can be. “Through it all, do not despise your small beginnings and do your best to wholeheartedly enjoy the journey—the good and the bad—because it’s never about the destination, but always about what you learn along the way... and for me, I learned that persistence is my superpower.”


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