How I broke down remote work barriers with mystery meetups

Our 246 employees work remotely across states, timezones, and countries. While our people love the flexibility of teleworking, it can make every department feel like a black box. And without in-office interactions, it’s hard to build a cohesive culture. But remote work doesn’t have to feel isolating. Here’s how we brought the watercooler to our scattered workforce. 

The problem: Remote work strangers

PureCars is fully remote, with employees sprinkled throughout 43 US states and Canada. Outside of the occasional department meeting, we rarely meet our colleagues in person, which meant employees had a hard time getting to know one another. 

We tried to fill the void with Slack groups for different hobbies (we have the cutest dog photos in #pure-pets) and get-to-know-you intros welcoming new folks to the team. But none of this was a substitute for more interpersonal chats that make work feel more engaging. 

Remote work also made our departments feel siloed. Our salespeople didn’t interact with engineers, who never spoke to the marketing team members, who rarely talked to finance staff. It got to the point where people had no clue what their colleagues on other sides of the company actually did day to day.

The solution: Monthly mystery meetups

One day, it hit me: what if, once a month, we introduced every person at the company to a colleague they never met before? They could get on a Zoom and talk about work, hobbies, and anything else they wanted. When I first had this idea, I assumed it’d be a hassle to organize. But with Rippling Surveys, it was a total breeze. Here’s how I set up PureCars’ mystery meetups:

Step 1: Set up a new survey

Using Rippling, I created a new survey that we now call “Coffee Confidential." In the app, I explain what it is, why we share it, and how to either participate or opt out.

Step 2: Send the survey monthly

The survey blasts out to every employee (unless they opt  out). We send a new one every month and leave it open for seven days. 

Step 3: Pair unfamiliar co-workers

Next, I go through the survey and pair participants who don’t typically work together. I mix departments and seniority levels so that even our CEO (who always participates) rubs virtual elbows with a colleague he hasn’t met. 

Step 4: Send prompts to break the ice

After I assign and notify pairs, we send out pre-packaged conversation starters. We nudge people to talk about their career paths, how long they’ve been with our company, their hobbies and interests, and maybe unpack a work problem they’re trying to solve. But they’re suggestions, not mandates. Once we assign meetups, pairs can set their own meeting times and talk about whatever they’d like.

The impact

Monthly mystery meetups make our scattered team members feel more interconnected. 

Stronger culture

Our entire office loves this new initiative. We sent a separate Rippling survey to solicit feedback and employees raved about these meetups. Many told me they enjoy getting to know new faces at the company and swapping stories with colleagues they don’t get the chance to work with. It also gives team members a better look into our company structure, and a better sense of different teams’ different job functions. 

CEO buy-in

Coffee Confidential’s biggest fan? Aaron Sheeks, our CEO, who insists we keep doing it monthly. Last month, we paired him up with a younger employee fresh out of college who’s thrived at his first job. Aaron loves meeting the members of our workforce, and has also dedicated his time to further employee mentorship.. 

Cost savings

Before I followed through on this idea, I was inspired by subscription services that can organize this type of mystery meetups on a company’s behalf. We paid for one at my prior employer, but with Rippling, we don’t have to spend money on a middle-man. The surveys are quick to create and easy to manage within our HCM.

This blog is based on information available to Rippling as of March 18, 2025.

Disclaimer: Rippling and its affiliates do not provide tax, accounting, or legal advice. This material has been prepared for informational purposes only, and is not intended to provide or be relied on for tax, accounting, or legal advice. You should consult your own tax, accounting, and legal advisors before engaging in any related activities or transactions.