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Getting Ahead

For This Startup CFO, Curiosity and Drive Are the Keys to Success (And He’s Hiring!)

smiling person standing in front of green bushes
Russell Lester, the CFO of Calendly.
| Courtesy of Calendly

Over the last 25 years, Russell Lester’s career has taken a number of twists and turns—from accounting to analytics to operations. He’s also worked for a multibillion-dollar company and was the second employee at a startup. As he gained experience and transitioned between positions, one thing became clear. “I realized I love doing several things: answering unanswered questions, solving unsolved problems, and helping fellow coworkers win,” he says.

Today, he gets to do just that—and much more—as the CFO of Calendly, the company behind the online appointment scheduling software. Lester oversees a variety of aspects of the business, including customer experience, legal, compliance, revenue operations, analytics, data science, strategic planning, security, finance, and accounting. “But more accurately, I work to empower our people to remove friction from the customer journey, bearing in mind that ‘customer’ includes both external customers and internal employees,” he says.

Here, Lester shares advice for aspiring CFOs, the secrets to his success, and the roles Calendly is currently looking to fill.

What attracted you to work at Calendly?

After meeting Calendly’s founder, Tope, and hearing about the opportunities available at the company to build out a number of operating functions, I became convinced that I could create a meaningful, tangible, and significant impact in the business. I felt that I offered Calendly some abilities, experiences, and mindsets that would accelerate the company in a number of areas that had lacked investment and focus.

I actually turned down my first interview opportunity because I didn’t realize how truly transformative Calendly is and can continue to be. My recruiter said I would be crazy if I didn’t take the interview, and her persistence paid off. When giving Calendly a second look, I experienced the product firsthand and began to think about how it revolutionizes workflow and productivity in a way I previously saw as a smaller problem. I now see just how impactful Calendly is for our customers and how much more potential there is for it to be the conduit that helps create richer, deeper, and more impactful connections between people. I also enjoyed the people that I met and saw how I could be an integral part of that team to take Calendly to the next level.

Why is it an especially exciting time to work at Calendly?

It is rare to be a part of a company that is growing so quickly, operating so healthily, building out new teams so aggressively, and yet remains so focused on delivering customer value and not losing sight on viral, product-led growth with a focus on our core values. There might never be another time in our careers where the combination of these focuses converges at the same time, and every employee has an opportunity to learn more, learn faster, and learn deeper about customers and themselves than ever before. I’d like to think that our employees see Calendly as a place that is among their greatest accomplishments when they look back many years from now on their career. To know we are a part of those milestones, memories, and achievements is humbling, gratifying, and motivating as a leader.

What types of roles is Calendly looking to fill in 2021?

It would be easier to say what we are not looking to fill! Really, as Calendly continues to scale, we are continuing to add new team members across all functions of the organization. That is the amazing blessing of being a part of Calendly in this dynamic market environment. We do not take for granted the growth we’ve achieved, the people that helped us get here, and the people it will take to grow beyond.

What are the remote candidate and onboarding processes like at Calendly?

Calendly moved to being a remote-first company in the summer of 2020. Our initial move to remote was to protect and preserve our number one asset: our people. As we saw how well we adapted to and thrived in a remote culture, we realized that the events of 2020 accelerated a move that we would have likely made a year or two later.

As a remote-first company, our people are accustomed to leveraging collaboration tools, attending Zoom meetings, bringing on new team members, and creating training and new hire processes that translate well without being physically present. My own team has doubled in size this year and of those new team members, I have not met a single one in person. Of course, many people miss the in-person, unplanned, and casual interactions that physical proximity allows, but if an office building and its aesthetics are the main manifestations of company culture, I would argue that it’s not a true and sustainable culture.

What do you like best about the company culture?

I have been generally struck by the genuineness and supportiveness of team members at Calendly. Everyone enjoys working together and wants to help each other achieve the bigger growth vision we all share. I also appreciate that our core values are not just words on a page. We talk about them regularly, we hire on the basis of them, and we coach ourselves and our teams to live them out each day. I also appreciate the ability of our leaders to partner together. We have our normal checks and balances as we consider various investments, strategies, and tactics, but overall there is a drive to achieve the mission.

What advice do you have for someone who is interested in joining the Calendly team?

Find someone who knows someone. Calendly is growing in visibility, popularity, and awareness and with that comes an applicant pool that is rich and diverse. The best way to distinguish yourself from other candidates is to be connected to someone that works here. Those network introductions are effective because there is a familiarity and trust in having worked with or known about that person’s abilities before.

Having said that, we’ve hired just as many people with no direct connections to Calendly. What makes them each stand out is their attitude, passion, and approach to working with the broader team. Subject matter expertise is expected and required. I consider that the “what” to someone’s work. What is not always a given is the “how.” How do you treat other people? How do you go about your work? How would you address a hard situation in your role? How would you persevere through adversity?

What skills and traits have helped you succeed in your career?

I often tell people that it’s my curiosity and intense drive. I love to understand how a business works and in cases where part of the engine isn’t working properly, I love to understand why. That curiosity fuels me to dig in. To learn. To explore. To ask the right questions that leaders should ask.

I then combine that with a drive that is likely borderline stubborn. I don’t like to accept failure, although I’ve failed many times. I don’t like to simply give up because something is hard. Most of the meaningful things I’ve accomplished in my career came through grit, tenacity, and endurance.

And it’s not curiosity and drive working independently. It is the combination of the two operating in a symbiotic relationship that I believe is part of the unique ability I bring to a company.

What advice do you have for aspiring CFOs?

I never realized just how much value there would be in adding the operational experience to my accounting, finance, and analytics experience. it made me better suited for and more capable as a CFO. I would now highly recommend any aspiring CFO to allow their career journey to take them into the operating side of the business. It allows the financial leader to have their pulse on the inner workings of the business, to hear the customer challenges, to see the struggles employees are facing, and to balance the need to fuel growth but in a way that is fiscally responsible. Doing this might be scary, but it’s worth the risk and will create a more well-rounded set of experiences that will be desirable for any high-growth SaaS company.