Reimagining the Water Cooler: Building Connection in Remote DTC Wine Teams

The COVID-era shift to remote and hybrid work brought many benefits: flexibility, broader talent pools, and increased autonomy. But it also came with a major cost—especially for those in the DTC wine world: we lost the spontaneous learning and camaraderie that happened naturally when we shared the same space.

Gone are the days of overhearing a colleague crush a club sales call or brainstorm a great pitch for a wine event. We don’t gather in the break room to compare Survivor predictions or poke our heads over a cubicle to troubleshoot a customer issue. Those moments—informal, unscripted, and deeply valuable—were how culture was shared, best practices spread, and new team members learned the ropes.

Now, our teams are spread across time zones and working from home. Our phone sales specialists might be in Oregon, our club manager in Omaha, and our fulfillment team hours away. How do we recreate that sense of connection and community when we don’t bump into each other anymore?

Why “Water Cooler Culture” Mattered More Than We Realized

Water cooler talk wasn’t just about gossip or pop culture—it was a vital source of organic professional development. Here’s what we lost:

Peer-to-peer learning from overheard calls and casual feedback
Real-time coaching from seasoned team members
A shared sense of team identity and culture
Opportunities to celebrate wins and troubleshoot losses

In the wine DTC world, where storytelling, connection, and nuance matter, these shared moments helped shape how we represent our brand voice and deliver exceptional hospitality.

Recreating Connection in a Distributed World

We can’t go back to those spontaneous hallway chats—but we can design new systems that foster similar connections, collaboration, and mentorship.

Here’s how:

Schedule “Virtual Water Cooler” Time

Dedicate 15–30 minutes each week for unstructured team time. No agenda, just an open Zoom or Teams room where people can talk about whatever they want—last night’s game, the weird club request they got, or the new rosé they tasted. These moments build trust, boost morale, and give space for organic conversations.

Use Tools to “Listen In”

Create opt-in Slack or Teams channels where team members can share:

Great customer interactions
Call recordings or summaries
Interesting objections they handled
Marketing copy they’re testing

Encourage voice memos or Loom videos to bring tone and storytelling into the mix.

Create a “Call of the Week” Culture

Designate one standout call, email, or club interaction each week to spotlight. Ask the person to break it down: what worked, what they’d do differently, what the outcome was. This is a modern version of overhearing the rockstar down the hall.

Build a Buddy System

Pair newer employees with veterans for monthly 1:1s—not formal training, just peer conversations. Encourage them to swap stories, compare techniques, and build relationships. This mimics that “tap on the shoulder” access to expertise we’ve lost in remote environments.

Bring the Team Together—Digitally and Physically

Hold quarterly virtual all-hands that focus on stories, not just numbers. Celebrate wins, share guest feedback, and invite different departments to spotlight what they’re working on. If budget allows, organize annual in-person gatherings or retreats to build deeper connections.

Standardize and Share Best Practices

Turn spontaneous insights into shared tools. Use a central knowledge base (Slack, Teams, Google Drive, Notion, Bloomfire, Guru, etc.) to house:

Call scripts
Objection-handling guides
Successful club email templates
Event hosting checklists

Make it easy for wisdom to be captured and shared.

Celebrate Curiosity

Encourage team members to bring one question to each meeting:

“How do you talk about the library release with high spenders?”
“What do you say when someone says: ‘I only like whites.’?”
“What’s your go-to move to increase club retention?”

These questions spark storytelling and collective problem-solving—hallmarks of a strong DTC culture.

Final Thoughts: The Future of Culture Is Intentional

The spontaneity of water cooler moments may be gone, but the human need for connection and shared learning is as strong as ever. As winery leaders, we need to be deliberate in creating spaces for that connection to thrive in new ways.

It takes more effort to build community across screens and time zones—but it’s worth it. Your team is your brand. The more connected they feel to each other, the more connected your customers will feel to your wine.

Let’s not mourn the water cooler—let’s reimagine it.

Need help fostering team culture, communication, and coaching for your remote DTC crew? WISE can help. Our custom workshops and leadership coaching programs are designed to support winery teams—no matter where they’re based.

Learn more at wineindustrysaleseducation.com