This week, 352 hosted Jon Smith, head of Customer Experience with Calendly. As a rapidly growing online scheduling tool, Calendly’s mission of making connecting simple so that people can do more is at the leading edge of remote working during COVID-19. Robert Berris, SVP of Innovation at 352, moderated a thoughtful conversation that touched on universal themes, including:

Excelling at customer experience means taking an organizational and cultural approach, not simply creating a department. Many companies see customer experience as the responsibility of a single team, but more progressive companies, like Calendly, think of customer experience as an end-to-end journey that crosses functions and teams. Someone needs to own defining that ideal experience for the customer, and then that vision needs to be distributed across the organization. Organizations have to ask themselves who owns the customer experience?

In SAAS, almost everyone is responsible for customer service when bandwidth is restrained. It’s not a matter of ramping up a huge customer experience team, but rather shifting how people think about delivering the ideal experience at every touch point. This shift can start with something as simple as sharing a customer feedback report to bridge internal conversations with the way customers are really experiencing your product. Even companies with lean budgets can create a cultural mindset focused on customer experience.

If you lead with your company values, everything else will fall into place. For Calendly, one of their core values is “start with humans”. The idea comes to life across the organization in many ways. Product teams are hungry for feedback and the business is putting people in place to connect with customers. You’re building the product and the operations for humans. If you’re not designing a process for someone, then who are you designing it for?

On a related topic, when thinking about partners, the first thing that is considered is the core mission – what makes connecting easier so people can accomplish more? That’s why partners like Zoom and Greenhouse make sense for Calendly. It’s the same when thinking about business priorities. Is the work in support of the mission and values of the business? Using that lens simplifies and accelerates decision making, and reinforces the values back to the organization.

Every company has its own path to defining momentum and success. Jon talked about how important it is for early stage companies to embrace the flywheel concept. It often takes a great amount of effort to get growth going, and then once the momentum starts, defining success can be interpreted in many different ways. For some, success is 10 new users a month, for others it’s 100. Defining that scaling point will allow companies to identify where growth in operations needs to happen. 

We loved that Jon is a fan of using the viability/feasibility/desirability model and design thinking to address operations and where the business needs to develop. Companies can use the “ilities” as guidelines, knowing that things at the beginning are not going to be ideal. Asking key questions like, “Where are customers going for help today?” “What is the desirability internally to help them?” “How do we take a low barrier of entry, like a free trial, and build it in a way that’s viable?” “How does the company know when to shift and change?” These questions can assist with critical iterative changes and progress.

Scale cautiously in the  COVID-19 world. What’s going on right now is a terrible thing for the world. People are being affected in so many negative ways. People are trying to connect in ways they’ve never had to connect before, and Calendly is well positioned for growth because of the circumstances. Industries are having to adapt and use tools in new ways.

By keeping close to their customers, and taking an empathetic approach, Calendly is considering new use cases and customer needs today, as well as in the future. As Jon noted, it’s hard to make product changes right now based on current information. There’s no way to be sure what the world is going to look like after COVID-19. 

What does scaling up look like for Calendly? Focus wisely is Jon’s motto. What is our team working on currently? What is important to keep moving and what do we need to divert resources to? That decision framework of “focus wisely,” helped Calendly and Jon’s team learn during COVID-19, and still move the business forward. 

Finally, we loved Jon’s answers to the question, “What would you tell a younger Jon?” First, he said, don’t reinvent the wheel. If someone else is doing something well, steal the idea with pride. Second, don’t hold back. Listen, create something, put it out there into the world, and iterate. There’s no better way to learn.

Want to know more?

Watch Robert and Jon’s live conversation, and join us each week as we talk to innovators about how they are navigating the challenges of their industries during COVID-19.


352 is an innovation and growth firm. Leading companies hire us to find billion-dollar opportunities, build killer new products and create hockey-stick growth. We bring grit and new-fashioned thinking to innovation, digital development and growth marketing.