Finding your successor: Michael Monteiro passes the CEO baton to Chris Litster

On July 1, 2018, Michael Monteiro will pass the CEO baton to his successor, Chris Litster, Buildium’s Chief Customer Officer.

Fourteen years after starting the company with co-founder Dimitris Georgakopoulos, Buildium’s CEO & Co-Founder, Michael Monteiro, has decided to step back and spend more time with his wife, Jennifer, and two children “before it’s too late, and my kids don’t want anything to do with me,” he says. Michael will remain with the company as a strategic advisor, and will continue to serve on the Buildium Board of Directors.

Today, Chris Litster manages the customer-facing teams of the business and is “a core reason we are seeing continued acceleration and growth rates north of 30 percent year-over-year,” says Michael. Prior to joining Buildium, Chris served as SVP and Chief Revenue Officer at Constant Contact, where he spent over ten years building the business through its billion-dollar sale to Endurance in February of 2016.

Chris Litster (left) and Michael Monteiro (right).

Michael and Chris met two years ago and felt a natural rapport from the start.

“I didn’t know Chris personally, but had heard a lot of great things about him,” Michael says regarding his search for a successor. “I knew I wanted an executive leader who had the full suite of go-to-market experience: sales, marketing, success, and customer care. Someone who reminded me of Buildium with a real passion for a mission-driven business and the small business market.”

Michael continues, “When we met, I felt real chemistry with Chris. I could tell he was someone I would trust to take on the role of CEO if that time ever came. And we talked about that; I knew this aligned with his ambitions, that he wanted to be a CEO.”

Two years after first being introduced to Buildium, Chris’s excitement is still contagious: “There was just something different about the company. It fit almost perfectly into what I was trying to do next. And meeting with the team helped me realize I was most interested in being part of a growing, small-business-focused, mission-driven company. This opportunity was unique. It checked all of the boxes.”

With a laugh, he adds, “It’s funny. I was talking with several companies at the time, and it was Mary, my wife, who pointed out what should have been obvious to me. She said that this was the company that I ‘couldn’t stop talking about.’”

Now, Chris will take on the new role of Chief Executive after having had the opportunity to “work side-by-side with an accomplished, inventive entrepreneur like Michael.”  

Michael shares some of what it was like to recognize it was time to step back: “I hadn’t aspired to be a career CEO. I knew at some point, I would want to step back. And I really thought through what would need to be in place to make that a reality. It boiled down to three core things: the business has to be in excellent shape; we need to have the right executive team; I need to have the right successor.”

Listening to Chris talk about his values and the culture that make a company last, you can feel the connection he and Michael share, and know that Michael could not be more supportive of Chris as his successor:

“The value of hard work and putting yourself out there has been ingrained in me since I was little, coming from my mom and my dad. The idea of not settling, not letting the world pass you by, and what I call the ‘sit in front and raise your hand’ mentality is what I learned to be the most important, as far back as I can remember. Life is out there for you to grab and if you can have an impact on someone else—get after it.”

Chris continues, “That’s why I love the small business audience, and that’s why I love Buildium. You can walk down the street and meet a customer; you can look to your colleague and know they live in an apartment managed with Buildium software. What we do is tangible to every person that works here.”

Chris explains that Buildium’s mission is underscored by an all-encompassing focus on the customer and the business: “Everyone here cares about the full funnel. It’s not just about quota for the rep or code for the engineer; it’s about the success of the entire company and how the whole is greater than the sum of the parts. When everything works well together, our customers win. And that means we win.”

“There are by no means playbooks or silver bullets to long-term success, but there are elements” Chris says. “If you align an entire company around a crucial mission, key goals, and how we make everything work together, the only thing that’s in front of us is us.”

Advice for the Transition

While Michael won’t be far, he has some early advice to offer Chris and jokes, “There’s a lot more that I’ll give you, don’t worry,” along with a few core takeaways:

1. Don’t lose sight of our vision and our mission, and don’t lose sight of the customer. We usually know what the right thing to do is, but sometimes what clouds our decision is all the other stuff that makes the right choice the hard one. Always go back to, ‘what should we do if we want to set the highest standard for the way business should be done?’ And when making tough decisions, take yourself out of it. Ask, ‘If someone else were to come into your role tomorrow, what would they do?’
2. Surround yourself with peers that have done what you want to do. Join a forum, identify people that you trust that can be a sounding board. CEO can be a lonely job. Make sure you have mentors and peers. Seek them out.
3. Continue to do things that don’t scale for employees, and for customers. It’s part of the special sauce. It’s what makes an experience different.
4. Stay accessible and stay human. The title can intimidate people so stay humble and remember that it’s always humans first.

Succession planning is often put on the back burner, but when done thoughtfully transitions in leadership can be smooth, transparent, and exciting. Propelled by its mission, you can feel that excitement here at Buildium today as it continues to strive for success and becoming a 100-year company.

Note: This post was written by Buildium’s VP of Marketing, Michelle Burtchell. It’s not often that a company has the opportunity to live into the idea of succession planning. As we worked through the details of the transition, I was in awe of the relationship that has been built between Michael and Chris over the years. I asked them to sit down and share some of what it was like to prepare to be CEO and to find the the right successor. Their insights are captured below. I hope you enjoy the read as much as I’ve enjoyed listening and learning from them. Congratulations to Chris, to Michael and to all of us at Buildium.