Sad, wilting desk plants. Film-covered coffee cups. Calendars still turned to March. When I popped into the Buildium offices a few weeks back, the abandoned desks were a sobering reminder that we’ve been at this work-from-home experiment for almost a year now. Yes, the vaccine is slowly rolling out, but there’s still no definitive end in sight.

Covid has brought many challenges to the way we work. But one of the most pernicious is the state of limbo that employees have been left in. Forecasts about office returns remain uncertain, as governments and businesses juggle ever-changing recommendations and rules. And…


On a recent morning, I had breakfast with 12 of our newest hires. But don’t worry — we kept our social distance.

Pre-pandemic, I used to do these breakfast meet-and-greets in-person over coffee and pastries. Today, we met on Zoom over bowls of cereal, mailed out in advance as part of a new-hire welcome kit. Nothing fancy, at all — but I left feeling pretty inspired.

Why? Because I had a chance to actually get to know the people behind the resumes and, maybe, show them that company values like belonging and pride are more than words in an onboarding…


If I think back to my first experience working from home — as a remote director with IBM back in the early 2000s — what I remember most is that damn blinking red light.

As “at-home” workers, we were told to leave our laptops open at all times and to stay logged into an early chat app called Sametime. When someone pinged you, it would blink red.

And you were expected to answer. Day or night.

Fast forward to today, and not only am I working remotely again but so is my entire team. It hasn’t always been easy, but…


A few months ago, a new employee joined our company. I knew he was an incredibly focused, driven guy. Detail-oriented, precise, all-business (in a good way). What I didn’t know was that he is also a human jungle gym … or at least his three kids seem to think so.

Mid-Zoom call this week, a giggling, tow-headed trio burst into his home office to crawl all over him. He good-naturedly rolled his eyes and tried to continue his presentation — flying kid elbows be damned. With this glimpse into his life as a parent, our relationship immediately, and incalculably, deepened.


I recently joined 75 of our employees on a Zoom call for something we called Morning Coffee at the Buildium Cafe. To be honest, it was a little chaotic. No one was talking about work. Some people were playing music. Some were in their pajamas. A couple of babies and several pets were even present.

And, from a leadership perspective, it was the best possible way we could have spent company time.

Plenty has been written about working from home but not about leading from home. As the head of a 200-plus person property management software company adapting to fully…


Earlier this year, gas explosions tore through my hometown outside of Boston, damaging hundreds of homes. I was at work when it happened. Immediately following the incident, I focused on making sure family and friends were okay and helping those who needed it. But I also knew we had customers in the affected areas. So the next day, I called them up to make sure they were safe and offer any assistance they needed. Reaching out didn’t seem like a big deal — just a natural thing for me to do. But their reaction showed me something. …


Unlimited paid vacation has become the perk du jour among hot startups and old-school companies alike — Netflix, Eventbrite and now even General Electric are among the employers offering it. But a flurry of recent headlines have dismissed the benefit as a cheap recruiting tool, a way to take financial liabilities off the books, and something that — in the end — employees don’t even actually use.

This is one side of the story, and a good caution for companies who want to get this right.

Buildium initiated unlimited vacation back in 2011, before this was a familiar concept in…


At the heart of every decision we make here at Buildium is our commitment to redefining the way that business should be done.

Nothing matters more to us than ensuring that we have the happiest customers and employees anywhere — and wherever possible, we extend that mission beyond our office walls, striving to make the communities that Buildium inhabits better places to live and work.

This November, we believe that it is our responsibility to both encourage and to empower our employees to vote. Every voice deserves to be heard. In 2014, turnout for the midterm elections was the lowest…


A number of months ago, I sat down to write a blog post for Underscore VC about the awesome opportunity I had around becoming the firm’s first Executive In Residence (EIR). Here I am, almost seven months to the day of that first blog post, and I’m writing again. This time, the reason is to look back at these great seven months I have had with Underscore as it is time for me to move on to my next opportunity as the Chief Customer Officer of Buildium, LLC. here in Boston. It is not a great surprise for me to…


Just about four months ago, I got in my car for what would be my last afternoon commute from Constant Contact — a company I called home for an incredible ten years. Over those ten years, in all the various positions I held at Constant Contact, I had the opportunity to help tens of thousands of small business owners — each and every one an entrepreneur — follow their dreams and make a go at building

Chris Litster

CEO, Buildium LLC, Husband, Dad, & Avid Skier

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