9 Questions with Roy Duvall, CTO at Calendly

For Roy Duvall, working for a company that understands what engineers need to feel energized and excited about the work they're doing, that is purposeful on dedicating time specifically for experimentation and innovation, and that insists on consistent interdepartmental communication for the smoothest flow of operations, was the honey that drew him into Calendly. As the Chief Technology Officer part of his job is to build teams, define processes and simplify complicated issues all in the name of bridging the gap between complex business needs and customer wants to find solutions that add value to and improve the overall customer experience.

Interested in joining the engineering team at Calendly? Read on for a sneak-peak into life in our most innovative department!      

1. What fascinates you most about engineering? 

"I always loved math, building things with my hands and solving technical challenges. When it comes to the field of software engineering specifically, I really fell into it by chance as I didn’t know the first thing about computers. I grew up near the poverty line and never touched a computer aside from a keyboarding class in 9th grade. However, I did know that Georgia Tech was often viewed as the best engineering school, particularly within the southeast, so it was where I was going to go. Since their Computer Science and Computer Engineering program had the highest exiting job placement rates at the time, it sounded like the degree for me. During orientation, I walked up to the Dean of Computing, asked how much I really needed to know about computers and he gave me the perfect answer. 'We have a ton of people that have been dabbling with computers and programming before they get to our school. We’ve found that the less you know when you get here the better because we don’t have to unwind the bad habits and patterns that one picks up without theoretical understanding.' I quickly responded and said, 'Well, I’m your man because I know essentially nothing!' In retrospect, I do wish I had known a little more going into it. I was definitely drinking from the fire hose but that’s really in a nutshell what got me into software engineering!"     

2. Give us a little snapshot of your career journey - what were those pivotal moments that led to your very respected title as CTO today?

"Even though I didn’t fully understand them earlier on, I always had an awareness that computer programs are simply executing logical methods that are consistent and have deterministic results. As others were frustrated by a machine, it drove a deep desire within me to understand said logic. Why did it break this way? Why did it do something I didn’t want it to do? How do I solve it? Computers are far from the magical black box that many perceive them to be and this really drove my computer engineering journey throughout. From day one I was solving complex algorithms, creating code and fixing bugs working for the Department of Defense. Quickly, I became more focused on bridging business and users’ perspective to explain how we may solve their needs. 

I found that bridging the communication gap translated into real business value. Building teams, defining processes, conveying the vision to solve a company problem really evolved to be my passion.

From there, I got really lucky and landed at the Weather Channel. I wore many hats there. I was constantly listening for the next business issue that needed to be solved and raising my hand to say 'Hey! I think I can help build a team to do that!'. That led to bigger and better opportunities. I was at the right place at the right time when they wanted to build a mobile presence. It was the first time I built a team from scratch and we found an amazing group of individuals that were able to carefully articulate business needs and expose what the customer wanted. Once the team was created, I trusted in their skills and expertise in turning raw data into a set of algorithms that provided real business insights that were presented to the stakeholders. Later on, I took my early successes from the Weather Channel and worked to improve and replicate them in healthcare IT with Sharecare.

While at Sharecare, Calendly actually found me. I wasn't looking at other opportunities and I was content with my role at Sharecare. It wasn't until I saw they recruited a Product Manager, Lauren Haile, whom I really respected that was on my team at Sharecare, that I took a call from a recruiter. The recruiter started the conversation with, 'hey there’s this scheduling company in Atlanta that is looking for someone to come lead their engineering team to grow it to match the speed the company is growing at.' I quickly responded asking, 'is it Calendly!?' The recruiter was taken aback by the simple fact I knew exactly who they were talking about considering Calendly was early on in their growth. Between Lauren Haile sharing her interview experience, Calendly's values and learning more from the recruiter, I realized that Calendly was and is a really special place and I needed to be a part of it."      

 3. What is the team like? What makes engineering at Calendly different?

"One of the aspects of engineering that is oftentimes difficult, is convincing the business of everything that engineering needs to be successful. What I have at Calendly is a Founder and CEO that understands 'that' and what 'that' is. 'That' can be a whole set of things. First and foremost, it’s providing understanding and transparency into end user interactions and that can be achieved through a true partnership with the Product team who exposes engineers directly to the end users rather than compartmentalizing that. Once Engineering partners with Product to talk to customers and understand their needs together, both sides of that equation can build a better solution. Tope started that early on and now it’s an ingrained practice at Calendly. In addition to that, understanding that Engineering is its own discipline and needs time to solve problems. We need time to fix things, to clean up messes, to fix patches and hacks and to make the system work the way it should. Tech debt is a negative word in most companies but here it’s known as a reality to be addressed. To us, it is important we carve out time alongside our daily tasks for innovation and continuous learning. We have Engineering time where teammates can make the system better, create on their own, and bring ideas to the company. We do company wide demos to show off incremental progress and enjoy innovation days where the entire Product and Engineering teams are given full autonomy to build something. Through these various and intentional practices, we’ve had some incredible innovations. As a leader at other companies, these ancillary efforts would compete against time put into the feature development that 'moves the needle.' But here at Calendly, there’s an understanding that all of those things are essential to moving the needle."            

4. What has been your proudest team moment? 

"There are so many it’s hard to pick out one. A proud team moment to me is one that exemplifies that the Engineering team understands what is happening with the business and gets ahead to ensure the system works the way it should. For example, we monitored our hockey-stick-like growth of meetings booked on any given day, and were prepared for a continuation of it. However, the engineers also knew from experience that at scale, the probability that there would be an exponential spike was increasing. Turns out the increase of vaccination appointments due to COVID-19 caused that exponential spike of meetings being booked from a million in a week to a million in a day and instantaneous booking requests spiking from 500 to over 30k per second coming into the system. Because the team understood our users and anticipated needs, we had baked in a caching layer for protection of our systems to ensure overall system stability. We did this behind the scenes without formalized requirements from Product, which we can attribute to the time and autonomy afforded to the teams to innovate and improve. The team’s proactive improvements kept the product stable and we were successful in scheduling millions of vaccinations as our site gracefully handled the traffic load in a time of extreme urgency."

5. Calendly is hiring! Why is now a great time to join the Calendly engineering team? 

"This year we are embarking on the modernization of our platform. There’s no better time to join Calendly than this year to have a major impact as an engineer, to evolve our system to global scale scheduling automation where in any given seat you are consistently innovating and designing new system components, at scale, with autonomy to drive the business success.

We are hiring all levels and types of engineers so there’s not a long list of technical requirements to be a Calendly engineer. Read our values because we live them. Be insatiably curious with a hunger to learn more. We are highly collaborative and thrive in front of and behind the scenes to solve problems for our users."

6. You value work-life fit and instill the importance of that throughout your teams. How do you make that work? What does work-life fit look like for team members? 

"Another attribute that makes Tope really special is understanding that while we need a sense of urgency to thrive, if we can’t disconnect, rest and recharge then we won’t be effective. I subscribe to that whole heartedly so we design our teams and processes to align with that expectation. As part of being highly collaborative, we share knowledge with great documentation, we create redundancy through pair programming and build code acumen with reviews and automated controls. These practices keep us from having single points of failure so the team can lift each other up and people can go on vacation without worry that something is going to drop."

7. The Covid-19 pandemic really disrupted a lot of business operations and so much more. How did your team maintain a sense of normalcy and even comradery during this intense time? 

"We rallied around the things that we know and love. Covid-19 affected us all in different ways so understanding the different needs for each team member was key. For some it meant they needed more space and time to deal with family obligations and for others it meant diving into the logical comfort and familiarity of work. Really it was an exercise in listening and striving to meet all the unique needs brought on by a time of mass uncertainty and rapidly changing times. As an engineering team, we were already versed with remote-first work. While there's no substitute for meeting in person, we kept and keep connection virtually with ice breakers, games and other virtual team activities. Though I will say, we are excited there are opportunities for us to get together in small teams and as an organization in the future. There is no substitute for getting a cross-functional team together with a white board and thriving on that in-person energy."

8. What are you most excited for the future of Calendly? 

"I have been a part of and led the journey from monolithic architecture to componentize services a number of times. I have made a lot of mistakes and learned a ton while continuing to meet business needs all along the way. I think at Calendly we have the opportunity to write a book on how to do this the right way. A book on evolving architecture, infrastructure, and application scalability while meeting needs of our users during exponential growth of the business. That’s what we’ve started working on this year and over the next 18-24 months, I’m so excited to see it become reality!"

9. Any advice for candidates looking to join your team? 

"Be You. We’re not looking for everyone to fit into a specific engineering mold. We are looking for unique candidates filled with a desire for continuous improvement, a passion for delivery efficiency, and an insatiable curiosity to add to our team. We will prepare you with an interview guide once you apply and all of the steps in our interview guide mimic a day in the life of a Calendly engineer. So, if you are energized by our interview process then you will fit very well here."