Sentaurs and Celebrations

At 9AM Pacific time, entirely too early for most West Coast tech employees, Sentry joined a video call and proceeded to take a journey. Curiosity became enthusiasm, sentimentality, surprise, and finally laughter. As the dust settled and people had time to process what they’d experienced, I was told to write a blog post. No festive deed goes unpunished.

The holiday party — an exciting or loathsome event depending on how much you have in common with your coworkers outside of work — is a staple at many companies. Sentry is no different. However, this year, with such events being impractical, if not ill-advised, we opted not to celebrate the end of the year this way.

Instead, the Creative Team orchestrated a special digital all-hands event, centered around the unthinkable — a holiday of our very own. The presentation began with The Story of Spectivus, an animated storybook telling the origin of a celebration in which we look backward, inward, and forward to analyze our mistakes.

Following the cinematic introduction came a toast from our founders, Chris and David, and our CEO, Milin. Hardships were acknowledged, achievements were acclaimed, and debatable celebration of the Dodgers’ World Series win was hailed. The end result was an expression of genuine thanks to employees that would surpass one’s expectations of authentic sentiment from the leadership of a start up.

With the company-focused component complete, the event’s festively adorned emcee pivoted the experience into employee’s homes. Those present began to open their holiday gift boxes which — where the postal services had prevailed — had arrived shortly before. A video grid of employees, once wearing business casual pajamas of their choice now looked indistinguishable, all happily donning knit sweaters bespeckled with centaurs and hotdogs, treated with an effect reminiscent of JPEG artifacts and CRT focus errors (those details make more sense when you work here).

At about this moment, with mics now unmuted, the audio landscape changed from crinkles and rustles, to questions of “Is this thing playing music?”, and finally into a cacophony as hundreds holiday boxes serenaded employees with syncopated Sentry holiday jingles, an experience that not even the packages’ progenitors knew was planned.

Behind every sweater, participants discovered a coloring book focused on the everyday struggles of contemporary centaurs — a reference Sentaurs, the collective noun for those that work for Sentry — in modern society. Finally, nestled deep in the kind of paper packing material that tangles nicely in the beard of even the saltiest operations engineer, was a copy of the first edition of Dumpster Fire, a card game we developed, dedicated to avoiding blame for one’s occupational foibles.

As the shock and excitement diminished, and just before awkward silence could descend, a video played showing Matt Robenolt, our resident YouTube celebrity, opened his gift. Employees watched with faces mixed with joy and disgust as he unboxed a special edition of the holiday gift, one just like theirs, but completely filled with baked beans.

Days later, a second wave of packages, a box of chocolates, arrived at everyone’s homes, tailored to their personal dietary preferences. Rather than go understated or predictable, we went for choc and awe — bold flavors, colors, and presentation. Our collective partners, children, and roommates have already consumed more than is rightfully theirs and for that, we are unapologetic.

Since I joined in 2016, I, Chris Jennings, and a select group of individuals on a need-to-know basis have produced holiday gifts for the team every year. This year, the entire Creative Team, and a few additional contributors were involved. As people open what we’ve created each year, we mumble fears betwixt one another that we won’t be able to top our efforts the following year. And yet, each spring we embark on new journey of whimsical mischief that we only slightly come to regret.

This year was special. It was a hard year. It was a year of new habits, processes, and logistics. It was a year in which making people feel included required big ideas, rigorous planning, and a healthy dose of opportunism. As the Creative Team kicked off the project in May, we were simply filling a box with things we thought were fun. As it became clear the holiday party wouldn’t happen this year and I began to realize the holiday season might slip by without being acknowledged, I saw an opportunity to create something memorable for the people I work with.

What we retrospectively come to appreciate as “company culture” is an ephemeral compilation of ever-changing, nuanced relationships, and happenstance. To wholly manufacture it is impossible and to force people to experience it is a recipe for disillusionment.

Instead, with Spectivus and the event that followed, I set out to create guardrails within which moments beyond my planning could naturally unfold and prompts to urge them to happen. Rather than propose traditions, we created a story that explained existing traditions. We began by presenting ideas and inspiration to people over video, but we brought the moments of excitement and surprise into their homes in a way that let them share the experience with their eyes, hands, and ears — and share it with one another. As we parted, we left them with feelings that were both warm and hard to reconcile.

In a year’s time, Sentry employees won’t likely remember the details of the holiday previous, but they will remember how it made them feel. If the team and I achieved the goals we set, we’ll have left the company feeling something no reasonable person should feel about a corporate holiday: excitement.