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Amy Fincher's Calendly Story

I remember the very first time I interacted with Calendly. A member from the coworking space I was working at sent me her calendar link to schedule a meeting. My immediate response was “What is this?!” It was such a convenient tool that I’d somehow never heard of.

I did a little online digging and found that not only was Calendly local to Atlanta, but they were listed as one of the best employers in the area… and they had an open position for an office manager. That piqued my interest and got me evaluating.

Hotel manager to office manager

I’d been working in hospitality for over a decade. I have stories that will make your hair turn white, but I also got to help people experience some of the most magical and memorable moments in their lives. During my time in hospitality, I’d done everything from helping a man propose from a helicopter, to obtaining specialty chocolates for Kesha, to dealing with unexpected bodies in rooms. I’d done everything and loved almost every second of it.

I also had the opportunity to grow exponentially in my career. I’d gone from front desk agent to GM of my own hotel. Was I ready to leave and be an office administrator?

You read all about Facebook, Google, and other tech companies that appear to treat their employees like prized possessions. In all my time in hospitality, that was something I’d never experienced. You work every Saturday and every holiday; you’re on call when a water pipe bursts in the middle of the night; you’re meeting an event coordinator at 4am to prepare for the day.

When I found Calendly, I saw a potential new life. In addition to a plethora of other benefits, Calendly offers unlimited PTO—something I’d literally never heard of—and a holiday break between Christmas Eve and New Year’s Day. I started picturing actually having time to enjoy a hobby and spend more time with family.

There were many reasons I wanted to work at Calendly, but were they worth working for? The grass is always greener from the outside. As I dug more into tech jobs, I found that flexible time off and plentiful snacks are pretty common base starters in the industry.

What made Calendly special?

I found that answer in a job review site. A former employee listed Calendly’s core values and was gushing about how, as a company, they use them to start and finish every decision Calendly makes.

The four core values are: Start with Human, Find a Way, Focus Wisely, and Strive for Excellence.

“Start with Human” struck a chord with me. I knew then that Calendly was a place I could easily transfer my love of hospitality and use it as a service and skill in an office environment. Now it was just a matter of actually landing the job!

The application itself was pretty typical: put in a resume, fill in your info, and wait. Well, I didn’t have to wait long. Less than a day later I received a very polite “thank you but no thank you” from Brent, Calendly’s former head of business operations (he's since moved on to be the CEO of his own company).

I accepted the “no” at first, but the more I thought about it, the more I knew I could do the job. I’d run an 125-room hotel and managed a four-department operations team.

I did something that I can’t actually believe I did now looking back and replied saying, “Are you sure? I really think I’m the person you’re looking for.” A day later, Brent responded and explained that Calendly really wants someone who has tech experience already, but he’s looked at my resume again and wants to schedule a phone interview.

A few days later, I met Brent over Zoom and we scheduled an in-office interview. Calendly has grown since Tope, Calendly’s founder and CEO, opened the first office in the Atlanta Tech Village. When I met the team they had already moved to a bigger office across the street from the High Museum.

I was told that—if I got the job—one of the office manager’s responsibilities would be to execute their next move before the end of the year, as they were already bursting at the seams in their new office.

After my meeting with the team, I was scheduled to meet with Tope over Zoom soon after. I remember him asking me why I wanted to leave my current job to be an office manager. I told him I didn’t want to be an office manager, I wanted to be Calendly’s office manager. I’d fallen in love with the idea of joining Calendly.

It was obvious to me that Calendly’s culture, people, and future were unique and special.

A few days later I got a call offering me the job and I was beyond ecstatic. A day later, my husband called me at work to say that a courier had dropped off a bottle of champagne and a welcome packet. How amazing was that?!

A life-changing career move

When I say working for Calendly has changed my life, it's not hyperbole. I stopped working sixty-hour work weeks. I had time to spend with my friends and family. For the first time in a decade, I had coworkers—not clients or employees—that I could actually make friends with.

My stress levels dropped and my health improved. Throughout my adult career I’d never considered having an actual work-life balance. Work-life balance is something every job tells you they have, but never actually gives you. Calendly gave me an opportunity to actually live.

Working for Calendly has exceeded my expectations and given me opportunities to develop surprising new skills. As office manager, I still get to bring a feeling of hospitality into the office and find ways to surprise and delight my coworkers in addition to being down in the trenches of business operations.

Calendly lives by “Find a Way” and when you work for a company that’s doubling in size every year, you just need to be in the room with your hand raised to be given the chance to take on amazing projects that will help shape the way you want the company to develop.

Calendly knows what got us here won’t take us there and welcomes input on improving processes every day.

Moving forward in the new normal

Our offices closed for COVID safety in March. Since then, everything has changed. I’ve shifted my attention to onboarding, employee engagement, and prepping the office for the safest return possible.

When Calendly was evaluating if and how to reopen, Tope agreed to work with me to allocate our substantial weekly catering budget to donate to local restaurants, that in turn donated food to local shelters.

During the early stages of civil unrest, Calendly closed for a day to give each of us a full mental health day, and then again to observe Juneteenth. I never imagined working for a company that actually puts its money where its mouth is for community improvement.

Calendly, like almost every company in the world, is adapting to the new normal. Going forward, we’ve decided to be a fully remote company and when the office opens again, coming in will be optional. As office manager, my role has and will continue to change.

Working for Calendly, I know that no matter what there will be a place for me, allowing me to Start with Human, Find a Way, Focus Wisely, and Strive for Excellence.


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