Feb 15, 2019

ON Partners Client Spotlight Series offers timely insights and strategies from leading global executives. In this spotlight: Chris Comparato, Chief Executive Officer of Toast discusses the unique leadership challenges of fast-growing companies, and the strategies he relies upon to succeed.


Spotlight ON_ Chris Comparata - Toast-1

Chris Comparato, CEO of Toast, has extensive experience leading high growth SaaS, software, and consulting companies, with a focus on customer success and building strong teams. Prior to Toast, he led all customer success functions at Acquia (named Inc. 500 #1 fastest growing company) and Endeca (acquired by Oracle in 2011). While at consulting firms Keane and Cambridge Technology Partners, his track record of delivering innovative business technology to diverse industries began.

Launched in 2013, Toast powers restaurants of all sizes with a technology platform that combines restaurant POS, front of house, back of house and guest-facing technology with a diverse marketplace of third-party applications. Pairing technology with a commitment to customer success, Toast helps restaurants streamline operations, increase revenue, and deliver amazing guest experiences. Toast was named to the 2018 Forbes Cloud 100 and recognized as the third fastest-growing technology company in North America on the 2017 Deloitte Fast 500.



Even before stepping into the CEO role at Toast, you served as a leader at a number of fast-growing companies. That gives you a great perspective on the challenges that fast-growth organizations present to their leadership teams. Tell us about that.

Chris Comparato: “The first thing that comes to mind is the amount of change you need to grapple with, and how to adapt to be ready for change. Then you also need to be ready for the pace of that change. So, while a company has grown and grown fast, as a leader you need to always think ahead on your priorities, expectations, and goals. How do you stay one step ahead and not get constantly pulled into the weeds? Part of the answer is, you’ve got to be a strong communicator and make sure that, if anything, you are over-communicating what’s most important. This includes, where are we, where are we going next, and why are we doing this?

We have a leadership development program at Toast. One of the things that I point out to new managers is that, within an environment of fast growth and continuous change—it’s really important to find the right balance, so that you’re in a comfortable position, even amid the rapid change and what might sometimes seem chaotic. Balance is essential, because when change is coming fast, it also may be unpredictable, and that balance can help you adapt.”

Those challenges are very significant.  As a leader, how should you respond?

Chris Comparato:  “At Toast, we rely upon some core principles. One is having a positive, solutions-oriented mindset. This encourages teams to approach any issue by brainstorming solutions right out of the gate. We’re also big on accountability—if there’s an issue on a project, who is accountable, who owns this, and what results are we aiming to achieve? You want clarity on these points.

To lead in a fast-growth environment, it is also important to be data driven. When faced with many decisions—which markets to open up, what people to bring on board, which customers you need to focus on, and more—being able to make a data-driven decision helps cut through the fog and reinforce that clarity. At Toast, we spend a lot of time working with our leaders and their teams on how to do this most effectively, and how to make the right hires for this type of environment.

Some other priorities relate to the company’s culture.  It’s essential to encourage the sense of belonging, of caring deeply about your team and everyone you work with. We foster this through our shared sense of community, purpose, and mission. When people feel this throughout the organization, then it’s usually the case that they can navigate change really well. They’re aligned, which means that we’re all driving in the same direction. And it’s important to keep communicating about this when hiring new employees. A company’s culture is dynamic, but if, as a leader, you stay focused on this, your culture will only be strengthened as you bring in more people and add new diversity to the team.

This is a pretty comprehensive approach to leadership within a fast-growth organization. How did you develop this approach?

Chris Comparato:  “In my career, I’ve had tremendous experiences in the organizations I’ve been part of—they’ve been growth-oriented, successful companies. And I’ve been fortunate to have had some really successful mentors along the way. I picked up golden tidbits from all of them, and here at Toast, I have been able to put all of this together with this wonderful group of people.

We’re aligned around the paramount goal of making our customers happy. At the end of the day, that’s what it’s all about. You may talk about fast growth, but what makes it happen is our razor-sharp customer focus. If you’re obsessed about customer happiness—which is how we feel every day at Toast—that’s what defines the culture and motivates us every day. Everything else follows.”



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