💻 How to Build a Winning Culture When You’re Miles Apart: Secrets from Remote Sales Leaders Who’ve Been There

“Culture isn’t something you create once. It’s something you commit to every single day — especially when you’re not in the same room.”

The world of work has forever changed.

As leaders, we no longer rely on hallway conversations, impromptu lunches, or in-office rituals to foster team spirit. For many of us, remote is the new normal — and that begs the question:

How do you intentionally create a thriving, high-performing culture when your team is scattered across cities, time zones, and screens?

This week, I had the privilege of sitting down with my friend and fellow sales leader Jeff Kirchick to tackle this exact question. What unfolded was a deeply authentic conversation about vulnerability, trust, leadership, and the sometimes unconventional methods we’ve both used to build remote cultures that win.

Let’s unpack the real takeaways — the stuff you can implement right now to foster stronger teams, deeper connections, and a sense of purpose that transcends geography.

The Remote Leadership Reality Check

Jeff and I both lead teams where Zoom is our conference room, Teams is our break room, and digital signals are how we measure presence and productivity.

The first myth we had to bust?

Culture doesn’t come from pizza parties or virtual happy hours.

Culture comes from consistency, clarity, vulnerability, and shared purpose.

What Jeff Taught Me: Vulnerability is a Superpower

When COVID first hit, Jeff did something bold. Instead of waiting for company culture to adapt, he became the spark.

“I started a workout class in the mornings,” Jeff said. “I called it Kerchfit — a play on CrossFit and my last name. It grew to over 50 people during the pandemic.”

Kerchfit became a ritual. A place for people to show up as themselves — sweaty, unfiltered, and real. Over time, it morphed into weekly meditation sessions and became a cornerstone of Jeff’s remote leadership style.

Key Lesson:

Vulnerability creates safety. Safety creates belonging. Belonging creates commitment.

Jeff shared another powerful example: his company’s on-site gathering where every employee, including the CEO, opened up about their personal “why.” Some were emotional. Some tragic. But all were real.

“When people share what drives them, it raises the stakes for everyone,” Jeff said. “You want to succeed not just for yourself — but for the people around you who’ve trusted you with their story.”

What I’ve Learned: Trust Isn’t Given. It’s Modeled.

I’ve had the honor of leading fully remote teams at Microsoft. And here’s what I’ve learned:

1⃣ Model. Coach. Care.

This is foundational to our leadership culture at Microsoft. I live it daily.

“I never ask my team to do something I wouldn’t do myself,” I told Jeff. “When someone doesn’t know how, I lead from the front and walk with them.”

If I’m asking them to prospect, you better believe I’m prospecting too. If I’m pushing on pipeline, I’m right there in the CRM with them. That’s how trust is built.

2⃣ Trust + Empower + Inspect

Remote work changes how you lead. You can’t micromanage from afar. But you can build systems to inspect what you expect.

Review forecast qualityTrack deal milestonesCreate space for coaching

“If the results aren’t there, we’ll examine the processes,” I said. “But autonomy starts with trust. And trust starts with belief.”

3⃣ Uncover the WHY

When I inherit or build a new team, I start with a survey.

Why?

Because I want to know:

How often do they want to connect?What do they want from 1:1s?Where are they trying to go in their career?What lights their fire?

If I’m not helping them get promoted, grow their income, or become a better version of themselves — what are we doing? I want to be a co-pilot on their journey, not just a checkpoint.

4⃣ Create Rituals of Recognition

Years ago, a manager introduced me to something called “DJ of the Week.” Every week, someone on the team gets to choose a song to kick off our call — based on a win, a best practice shared, or just something that stood out.

It sounds small, but the impact is huge. People want to be seen. They want to be celebrated.

And beyond that, I encourage “players-only” meetings — spaces where the team can meet without me. Because they need time to vent, brainstorm, laugh, and collaborate on their own terms.

Bottom Line: Culture is a Daily Choice

What makes culture work remotely is what makes it work anywhere:

Trust

Transparency

Vulnerability

Recognition

Shared mission

You just have to over-index on it when you’re not together physically.

“The goal,” I said to Jeff, “is to create a culture that exists and thrives — even when they close their laptops for the day.”

Practical Actions You Can Take Today: Send a team survey to uncover communication preferences and personal goals. Share your own failures and growth moments with your team. Start or re-center on your team’s “why” — personal and professional. Introduce a fun ritual like “DJ of the Week” to drive recognition and energy. Empower “players-only” meetings so your team can bond organically. Lead from the front. Do the hard things. Let them see you doing it.

What are YOU doing to build culture across your remote or hybrid team?

What’s working?

What challenges do you face?

#RemoteLeadership #CultureMatters #ModernSelling #SalesLeadership #TrustAndTransparency #VulnerabilityInLeadership #LeadFromTheFront #HighPerformanceTeams #FutureOfWork