Five9’s CEO has one simple mission: End bad customer service.

Flight Templates are templated flights, or sets of questions, written by some of the world’s preeminent business leaders. With Flight Templates, Balloon users get unparalleled access to seasoned perspectives and proven business strategies across all areas of business, including leadership, product, marketing & sales, innovation, employee experience, culture, and more. This feature is part of a series on The Insight that profiles Balloon’s Flight Plan authors.


Think back to your most recent customer service experience.

Did you talk to a person? Did they have the right information ready? Did your problem get solved? Did you leave feeling heard, or understood, or satisfied?

Rowan Trollope, the CEO of Five9, one of the leading cloud contact center SaaS platforms, thinks there’s a good chance you would answer “no” to most of these questions.

If you asked your friends about it, I think about eight out of ten would tell you that it was some horrifying experience,” Trollope said. “Maybe they were waiting on hold forever, or caught in crazy menu trees, or they were hung up on or stuck talking to a bot, et cetera. It would just be bad, and that's generally what you'll hear.”

Trollope—a vocal champion of innovative, personalized customer service in both his current position and his previous role as Cisco’s Senior Vice President and General Manager of Cisco’s Internet of Things and Collaboration Technology division, which he held until his transition to Five9 in 2018—knows that customer service’s reputation for providing customers with more frustration than help is no accident: On the contrary, in many cases, it is a deliberate effort to drive down costs in a department that companies have seen, for years, as a last priority. (At Trollope’s first software job in the early ‘90s, the new Head of Support’s first priority was to make the company’s customer service phone number more difficult for its customers to find so that they couldn’t call. As he recalls, 18-year-old Trollope was “absolutely gobsmacked by that plan.”)

It’s a decades-old strategy, but, thanks to innovators like Five9, it’s customers , and Trollope himself, it’s aging out. 

Five9, a public company with a multi-billion dollar valuation, is one of the most lauded customer service SaaS companies in today’s market, due in large part to Trollope’s emphasis on utilizing design thinking and building clean, simple UI in every product update. Five9 is leading customers across industries toward a future where happy customers and high profit margins aren’t mutually exclusive, but go hand in hand.

The IT and customer service industry spends nearly a third of a trillion dollars globally every year. From a business standpoint, if we’re spending that much to deliver something that basically no one likes, that's just insane,” Trollope said. “But now what we’re seeing is, thanks to the rise in Cloud adoption, the dominance of SaaS, and the continued acceptance of subscription based pricing models, it’s starting to enter the wider consciousness of business leaders that the ability for customers to switch their product or service provider is much easier. This leads to customers valuing the brand experience more than the product itself. Customer service experience becomes a new expectation versus a nice-to-have.”

Research proves that the industry is in flux and headed toward a model more like the one Trollope describes. Earlier this year, Simplr, another cloud customer contact software company owned by Asurion, reported that 51% of customers will never do business with a company after one bad customer experience, resulting in an annual loss of more than $75 billion every year for U.S. companies. And according to a 2021 survey from Gartner, a leading research and advisory firm, the majority of business leaders plan to prioritize and drive value with a proactive service model.

With the IT and customer service industries on the brink of total transformation, Trollope has crafted a three-part flight template series, Transforming Customer Success, to help your company build tangible strategies to turn hesitant customers into your most loyal buyers and brand cheerleaders.

  • Customer Service Audit
  • Improve Your Customer Service
  • Design Thinking to Improve Customer Experiences

No matter your industry, the discussions and strategies that Trollope’s flight template series will surface are vital, because these days, Trollope says, every business is a service business.

“Basically, because of the Internet and the exponentially growing connectivity of things, there’s now an economic incentive to provide great service and build positive relationships with customers in a way there never was before—because if you don't, those customers will leave you,” Trollope said. “My mission is really simple, four words: ‘End bad customer service.’ That permeates not just our culture but also our incentive model. At Five9, we have the best customer service in the industry, hands down, but we're not doing something heroic. It's for our own self-interest, but that's always the best thing when self-interests align with things that happen to be good. And that does work. It's worked for us.”

Check out Rowan Trollope's Flight Template Series

CEO, Five9