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How to Build a Successful Remote-First Company

It seems that the remote first work environment is here to stay. That has resulted in a renewed focus and emphasis on the employee experience. We sat down with Calendly’s Manager of Engagement, Jordan Conway, to learn more about her and her team’s work as Calendly continues to evolve into a remote-first world. 

How would you define “team member engagement”?

“I define team member engagement or team member experience as the focus on creating community and connection at work. If you are engaged at work, the data suggests a number of positive impacts to not just the individual and teams but also to the company more broadly.  A 2022 Gallup survey suggests that companies with a highly engaged workforce have 21% higher profitability and also 17% higher productivity than companies with a disengaged workforce.”

What were some of the key challenges you were solving for when Calendly became remote-first?

“I first joined Calendly’s Engagement team as the Program Manager of Onboarding and then transitioned into my current role. While I wasn’t responsible for managing the closing of Calendly’s office in Atlanta, I was a part of the team who handled that transition. Everything we once did in an in-person setting had to be shifted to a remote-first environment.  What does a remote first environment look like? Think about moving our recruiting and hiring process from an in-person experience to a remote one. What does that look like? How do we think about that differently and maintain a high touch experience? Similarly, how do we create water cooler happenings in a virtual space? All of these questions and more all while thinking about the solutions across a multi-generational workforce.”

What mistakes have you seen in the marketplace with remote-first companies and engagement?

“I think some companies aren’t doing it at all. They are simply relying on managers and/or teams to figure out and drive engagement independently.  There aren’t a ton of company wide opportunities to be engaged together and interact and thus, it happens in silos or worse, not at all. I also think companies tend to overcomplicate what engagement is. It doesn’t have to be an event. It could be something as simple as leveraging Slack to drive engagement. We have leveraged that here at Calendly with our Cal Pals through an Employee Appreciation campaign where we encouraged individuals to share their appreciate with another team member or when we recognized Trans Visibility Day and encouraged our Cal Pals to drop a memory or a warm fuzzy about someone in that community. There are a variety of ways to keep things simple while still driving engagement with your people.”

What are some of the challenges you are looking to solve in the future?

We are working on building a regular event cadence company wide. We are aiming for twice a quarter where my team will facilitate a synchronous event or ILE (instructor led event). This could be anything from music bingo, a mindfulness session, costume contest for holidays like Halloween or even a talent show. We use a variety of tools to help our people feel engaged during such gatherings.  We typically use tools such as Zoom, Loom, Gatheround, Jamboard and Kahoot to name a few. We also are looking to host two company wide retreats each year. One would be in-person while the other would be virtual. Outside of events, we want to increase awareness across our teams through internal marketing, get our managers more involved and ensure we have engagement strategies that accommodate all of our Cal Pals. For example, we just had some members join our Customer Experience team who work night shifts so we are needing to think creatively on how to give them the same team member experience as others.”

What would you tell companies who are starting from scratch on their virtual engagement efforts? 

  1. "Keep it simple. There are a lot of tools with free versions that you can leverage to make your engagement efforts easier: Kahoot, Jackbox Games, Pictionary, Garticphone.
  2. Have a strategy and stick to an internal communication schedule to drive awareness and buzz internally across your people. 
  3. Involve your cross-functional teams to lead sessions and or be guest speakers on topics your people are interested in. You can then utilize them to advocate for larger more holistic programmatic initiatives moving forward.”

What is unique and or innovative about Calendly’s remote-first environment?

“While we are still early on our remote first journey, we have buy-in with leadership to experiment, try new things and tools. Having a company-wide in-person retreat is still relatively unique for companies and something our Founder and CEO Tope Awotona and our Chief People Officer, Jeff Diana feel very passionate about.  Our people make it special because they want to feel engaged and connected at work and thus are strong participants in the work my team does and events we create.”

What do you want to see for the future of Calendly’s remote-first environment?

“It sounds silly but honestly having consistency for my team and our Cal Pals. Since we’ve just begun this work, we haven’t had a chance to get deep with it and get consistent feedback to continuously refine and improve our strategies and efforts. 

From that I am excited to flex my team’s brain power and explore more creative options beyond speakers and events into true innovations for connection.”

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