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Professional Development

How an Apprenticeship Is Cultivating Career Changes From Within Calendly

Gabi Gaines graduated in 2019 from the University of Georgia and launched her career at a small start-up. She was 1 of 12 team members, so as expected in early start-up life, she wore many different hats. “I was doing everything from Customer Support, to Onboarding, to QA. Wherever we needed a body, I was there to jump in. This opportunity gave me a lot of valuable experiences and exposure to different parts of the business.”

Shortly after she began her new venture, and like so many in 2020, Gaines was impacted by the sudden onset of Covid-19 and her role was eliminated. “With Covid-19 impacting the job market, job hunting just dried up. I decided to take a real break and moved to California to experience a different life. In early 2021, I was referred to a role at Calendly and that’s when my career adventure really began.”

Gaines joined Calendly’s Customer Experience team in March of 2021 as a Senior Product Specialist. “I quickly became one of the top performers when I started. I think that comes down to the fact that I love learning and truly enjoy my work.” Soon after kicking off her career on the Customer Experience team, a new opportunity was presented to Gaines in one of her team meetings. A new initiative was created from the Engineering team with Roy Duvall, Calendly’s Chief Technology Officer at the helm. It was an apprenticeship style program that would open the door to Customer Experience team members to learn and work within the QA Engineering team at Calendly with the potential and ideal outcome being a full time role on the QA team.

“[My manager] presented the apprenticeship idea and qualifications necessary in a team meeting. From there, anyone interested was required to attend a day in the life session of a QA Engineer to determine if it was a good fit for you and something you wanted to pursue. I told myself, ‘It's three months. If I hate it, the worst thing is that I learned something new and know that this isn’t a path for me.’ But to  my excitement, during the day in the life, I knew that this was absolutely the next step for me! I applied to the apprenticeship, and was so elated when I got it! Being able to have somebody pull you into a department and say here are the skills you need, here is the work you’ll be doing and giving us the opportunity to truly change careers without having a certification or going back to school is pretty amazing. I’ve never seen something like this happening at another company.”

Gaines is one of two Customer Experience team members selected for the apprenticeship. In the eyes of the Engineering team, knowledge and insight into what customers want from our product is invaluable and why team members like Gaines are looking to bring valuable customer knowledge to Calendly’s Engineering team. “It’s pretty cool knowing I have an impact on the product and features that our customers need.” When asked what the most surprising thing has been thus far in joining the Engineering team, she paused and smiled. “I am surprised by how passionate people on the team are about this place and the product. I was fortunate to meet some Engineering team members in person and the first thing one of them said to me was, ‘You’re already a part of our family. We want you here, we want your experience, we want your skills, we want your knowledge.’ I never expected people to be that passionate about wanting me to succeed and win.”

As part of the apprenticeship, each apprentice receives a mentor who currently works on the QA team. Lisha Brown is one of Calendly’s QA Engineers and at first had hesitations on being a mentor for this program. “At first I was concerned about managing the additional responsibilities of being a mentor. But now, I realized it reinforces our QA principles and standards within the team. I was fortunate to be paired with Gabi. Her eagerness to learn encourages me to seek guidance from other team members where I may be unsure of something in my own [work]. Seeing how encouraged she is to grow and learn more and help our clients has gone viral. This program has helped morale within QA and Support and it has started to build bridges across teams through conversations in this remote world we live in. Getting to shape someone's idea of what QA is, explain the fundamentals and how and why Calendly applies them to our processes is truly incredible.”

With newness comes excitement and at times, nervousness. Both are familiar to Gaines as she begins this adventure. “I have general anxiety and it comes out when I interview. I have confidence in my skills and abilities. It's more of the component of selling myself and articulating my work simply that I find challenge. So, the interview at the end of my apprenticeship is something in the back of my mind making me nervous. To keep my nerves at bay, I like to remind myself that they chose me for the apprenticeship for a reason, and I have the skills, knowledge, and resources necessary to succeed! And best of all, I am surrounded by the best team who all obviously want to see my success as well!”

“Since my first day at Calendly, I’ve been surrounded by people who uplift me. As part of the LGBTQIA+ community, it is extremely important to me to be loved and appreciated for who I am, and no one at Calendly has ever made me feel otherwise. The culture at Calendly has always made me want to be here and wake up every morning excited to go to work, so I’m truly so grateful for the opportunity to advance my career at Calendly.”

And as for the future of Calendly, what gets Gaines excited? “I see Calendly growing so much bigger than where we are today. We have such an amazing and unique product. We certainly have competitors but they don’t have the reach we have. I love when I run across Calendly links in the wild. It shows we are really making our mark on the world.”

Gaines will complete her apprenticeship in August of 2022 and is hoping to join the QA team as a QA Engineer.

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