Meet The Customer-Driven CEO: An Interview With Toast’s Chris Comparato

By Drift


Meet Chris Comparato. He’s the CEO of Toast, a Boston-based SaaS company turning the restaurant industry on its head. The android-based company landed $30M in their Series B lead by Bessemer Venture Partners, with participation from GV, the venture arm of Alphabet (FKA Google Ventures). Pretty good vote of confidence when the creator of the Android platform wants to invest in your tech.

Chris_Comparato.pngWhile Toast’s brand is gaining momentum with 1700+ customers across 45 states, people don’t know a lot about Chris’ rise to the CEO role, and why he’s so unique.

Chris spent his entire career in roles driven by customer success KPIs. Prior to Toast, Chris was SVP, Customer Success at Acquia, prior to that the SVP of Customer Solutions at Endeca, and prior to that a long history of roles in services, solutions, and relationship management.

Essentially, Chris has lived his entire career at the intersection of great SaaS products and customer happiness. His energy and passion comes from seeing customers benefit and improve from the leverage they get out of a great product, and not just at a point in time but on-going. Chris is not shy to point team members and peers to stories of making customers happy across hospitality, retail, ecommerce, sports, the government and media organizations.

What do SaaS businesses care about? Acquiring and retaining customers.

What does Toasts business look like? While I can’t share specifics, their customer growth is off the charts, and they’re as close to negative churn as I’ve seen, in a space that is accustomed to businesses not making it. And their ARR is steadily climbing with the introduction of new capabilities. Simply put, they’re killing it.

But, back to Chris. I recently had a chance to sit down with him and talk about his unique rise to the CEO position, and what it means for Toast. Here’s our chat:

Q: How did running customer success prepare you to run a company?

I can’t tell you how many sleepless nights I’ve had in effort to make customers happy. When you’re running customer success, you’re accountable for your customer and you better be passionate about it. The CEO has a host of things he or she cares about, but my responsibility was always oriented along the dimension of customer success. I was responsible for the experience given to a customer, and walking in their shoes along the entire journey from the initial sale to the happy state.

There are so many intricacies to running customer success. You need to know the customer, what drives success for them and their business. You need to know the product cold, and understand customer challenges and expectations with it. You need to push the product organization to build better products based on that customer voice. You need to build and coach for empathy with a team of people responsible for the daily interactions – whether that’s by support or any other customer facing function. The selection of the right people and the ongoing training to make sure their customer interactions reflect your brand never ends. And don’t forget, the majority of your time is spent talking to customers. In short – you’re an expert on the product, customer pain, and a builder of a team that creates a best-in-class customer experience. Expert, relationship manager, team builder, customer advocate.

So looking back at my career, I was subconsciously training for this role all along.

Q: At Toast, “Everyone is responsible for customer success.” What does that mean?

I’m a big believer that when you only assign “customer success” responsibility to a specific team, yet an entire organization interacts with the customer, you set yourself up to fail. You lose visibility to all of the touch points, create tension, and you don’t have quality control over every interaction. Like an orchestra playing music without a conductor.

We’re trying to build an experience that amazes our customers from the beginning, and never ends. We’re obsessed with keeping our customers. If there’s one thing I care about, it’s that I have happy customers that never leave and see value from what we are doing.

To make this a reality, we’ve spent a lot of time mapping out our Customer Journey (thank you to my team, I know I can be a pain!) and institutionalized what we learned to create the right process. It is always evolving. There are distinct roles and responsibilities for who interacts with customers when. We have guardrails that protect our customers from going off track when they’re onboarding. We have satisfaction metrics in place for each journey stage. Our goal is to be crystal clear who talks to customers and when, so there’s no internal confusion to us nor the customer. This ensures our customers have an optimized experience based on the stage they are in, the products they are using and any situation that they may have encountered.

Q: What do CEOs who don’t have a customer-focused background lack?

In my experience the majority of CEOs are more sales-driven or product-driven. They each are very effective areas of strength, but sometimes may pose challenges.

The Sales-Driven CEO: In the early days, customer acquisition is the #1 focus. This CEO invests heavily in marketing and sales, with a bookings focus and less in the product or customer. As renewal cycles start to approach, you can easily be caught on your heels having missed major red flags with customers or the product along the way. The ability to effect positively effect churn may freeze you. It can be easy to obsess over top line growth as the most important thing, when I’d argue making small batches of early key customers super successful is a better objective to chase, and you are then building muscle on the customer experience as a whole.

The Product-Driven CEO: This individual is either a technical founder, or a professional product CEO. They obsess over the product – features and functionality. They’re usually incredibly visionary, but well ahead of customer pain and needs. Once they have customers, they obsess over growing lifetime value perhaps through more new products. It’s easy to take a shortcut on product development here or there just to get it out, because launch events are meaningful to the business. But I’ve seen too many products launched prematurely which result in customer nightmares, and the business is not better for it. I’ve also seen a focus on breadth vs. depth when it comes to the customer relationship which can be equally ineffective.

I’m guess I am calling myself a Customer-driven CEO.  In a successfully growing SaaS business, the flywheel of attracting, enhancing and retaining happy customers is center. It means I often start with the customer and work from that dimension when looking at the customer experience including what to sell, what to build or enhance, and the customer’s journey once they are on our platform. Today I still have several meetings and calls a week with customers. Some brand new, some old, some happy, some perhaps not. It gives me energy and is my mission to never lose touch with what our customer needs and wants, and I push all of my teams to be customer-driven. It is at the center of our flywheel as a company.

Q: Just for fun, what did running customer success not teach you about being a CEO?

Great question, I would say many things. One prime example is how the customer and user experience of the product itself could have a comparable happy impact vs. someone taking or making a call. The customer journey is not just enhanced by people, but likewise by product.

So why should your head of Customer Success be your next CEO?

  • They’ll create a customer obsessed culture
  • They’ll align the organization around providing the right products and customer experience
  • They’ll have the lowest churn rates.