Team Performance

8 Questions with Calendly’s Director of CX, Joelle Waksman

At Stella Connect we strive to provide CX professionals with fresh and actionable resources. As we enter the new year, we’re ramping up our interviews with CX industry thought leaders.

Calendly is a scheduling tool that allows users to schedule meetings without the back-and-forth. The team works hard to create a smooth, simple tool that takes the work out of connecting with others so our users can accomplish more.

We sat down with Joelle Waksman, Director of Customer Experience at Calendly to learn how she built a meaningful career in CX.

Joelle Waksman

Joelle Waksman

Director of Customer Experience at Calendly

1. Tell us a little bit about your career and how you ended up where you are today?

I started my career as an SMB Support Trainer at Yext in New York City. It was an amazing, vibrant, team of hard-workers who were straight up hang-up, pick-up all day long teaching and training users on the dashboard. From there, I helped develop a brand new Enterprise Support team from its infancy, supporting a specific group of Enterprise customers and their clients. Through this experience, I found my love for people management specifically in the customer support space.

The time came unfortunately for me to leave the concrete jungle and find greener pastures (literally) in Atlanta, GA. Where I found an amazing opportunity at a start-up, Calendly. I started here as the first Support Manager for a team of 4 and quickly expanded the reach for Calendly’s ever-growing customer base. The opportunity arose to step up in leadership while managing the support team, success team, and content management team as the Director of CX!

2. What do you love most about working in customer experience?

I think inherently, I’m a people-pleaser, and CX is an industry that challenges that yearning for doing right by others every day. You have to think empathetically, and realize that each situation is unique. Needing to simultaneously think broadly and granularly in the same moment is very exciting. Plus, you get to solve people’s problems, make their days, and surprise and delight!

3. How does your team contribute to the success of the larger business?

I think CX, in all companies really, is a huge chunk of the foundation of a company’s success. You need people to buy your product, and if customers are unhappy with the experience then it’s that much harder to sell your product. Customers will always need help and the CX team helps to solidify what our users already know––that Calendly is a game-changing software that’s easy to use and totally worth it. Quantifiably, we impact retention, activation, and expansion. The satisfaction of our customers is a huge metric measured company-wide, as well.

4. How do you measure your team’s performance?

We focus primarily on CSAT scores, resolution rate, first response time, ticket activity, deflection rate, average total requester wait time, and more.

5. What does your CX tech stack include?

We utilize Zendesk as our ticketing and chat platform, as well as the host for our Help Center. We use Slack internally for communication, Stella Connect for CSAT and customer feedback, Solvvy for deflection and self-service, Algolia for optimized search functionality, Zoom for conferencing, and we just implemented Lessonly for onboarding and certification.

Learn how Calendly built their CX tech stack in our upcoming webinar: The Building Blocks of the Ultimate CX Tech Stack

6. What are the biggest challenges you face today?

Calendly is growing fast, it’s amazing and challenging as we work to scale the customer experience alongside the larger business. We have an incredible team and it’s important we maintain quality, so we have to make sure we have enough hands on deck to manage the volume and maintain YoY growth and seasonal spikes. We’re working hard to allow for time outside of the inbox to focus on career growth, team efficiency projects, and more, while still maintaining a world-class customer experience.

7. Where do you see the customer experience industry going in the next few years?

The yearning to self-serve by most software users is highly underrated. People don’t want to speak to support, they want to get the answer and they want it to be easy. I think AI and machine-learning self-service tools and in-app help content is going to be the trend in the very near future if not already. Customer-centric ticketing, allowing an agent to view and understand the entire story of the customer, is also going to be important moving forward. CX teams will have to shift their focus onto understanding the entire story and business goals of each particular customer to provide the above and beyond experience users are expecting.

8. What advice would you give someone who wants to get started in CX?

If you want to get started in CX, you likely have a bunch of kind, empathetic, genuinely caring and curious bones in your body. That’s a great and important place to start. You need to feel a genuine desire to do right by others and help people be successful. CX can be taxing, emotional, sometimes monotonous, but if you are driven by those core values you’ll find every day to be an exciting new challenge to learn from.

Bonus Question: How has working with Stella Connect improved your CX function?

Stella Connect has flipped our CX function on its head. Before, we were struggling with receiving accurate feedback, separating experience and product function, struggling with team morale and all types of uncertainty. Now, we have a crystal clear picture of the experience we’re providing, how to improve on each individual ticket and a consistently exciting way to go above and beyond for our customers.


Interested in being featured in our 8 questions series?

If you’re a CX leader and would like to be featured in our 8 questions series, please e-mail marketing@stellaconnect.com and a member of our team will be in touch.

Learn how Calendly built their CX tech stack. Register for our upcoming webinar: The Building Blocks of the Ultimate CX Tech Stack.