Part 4 - Building Community

Culture and Community Start at the Top

Throughout my career, I've worked at companies that truly prioritized building something special as a team — where everyone contributed their unique strengths in a collaborative environment that balanced community-building with accountability. I've also worked at companies where the executive team wasn't invested in fostering culture or community.

In those cases, as a senior leader, I knew it was up to me to step up and build the community within my team.

Here’s how I did it:

Take Action — Don’t Wait for the Perfect Time

When I stepped into a senior leadership role during a re-org, the team was facing a lot of uncertainty. I didn’t wait for all the answers. Instead, I immediately began problem-solving.

The first step was introducing myself and addressing the uncertainty directly. Since it was the holiday season and many were out of the office, I created short video messages to communicate asynchronously with the team. This allowed me to address key concerns and share a vision of what we would build together without pulling people away from their families. The feedback was overwhelmingly positive, as the team had been struggling with a lack of communication from executive leadership.

Launch Your Team with Purpose

Once things settled down, I scheduled an all-hands meeting to formally launch the team in mid-January. This meeting was crucial for laying out the guiding principles, explaining the new org structure, and setting clear expectations and cadences. It also allowed me to connect authentically with the team.

One memorable moment: I dropped an F-bomb while expressing the need to break away from the mindset of "We’ve Always Done It This Way." Surprisingly, it became a rallying cry, and I strategically used it to motivate the team going forward! (There was even a counter deployed in follow up meetings)

During the launch, I introduced a new team name—The Phoenixes—to symbolize our grit, strength, and ability to rise through change. This wasn’t just a catchy name but a symbol of our collective adaptability.

Celebrate Wins and Recognize Contributions

Enterprise sales is tough—deals can take 6 to 9 to 12+ months and it's a grind. The payoff when you win is huge but you also can get lost and disenfranchised in the middle. As a leader, I made it a priority to celebrate the small wins that lead to the big ones, like booking a key discovery call, getting a verbal agreement, gaining a referral to a new business unit, or building a new champion within an account.

We also celebrated team members' personal milestones, like birthdays and work anniversaries, adding them to leadership calendars and publicly acknowledging them. These small gestures meant a lot to the team and fostered a sense of connection.

Create Regular Recognition Moments

To keep momentum going, we scheduled quarterly recaps focused on celebration, enablement, and recognition. We highlighted closed deals, gave shout-outs to individual contributions, and presented awards. My favorite part was the “Above and Beyond” section, where team members could nominate colleagues who made a significant impact. These nominees were publicly recognized with a personalized slide and a small gift.

While it took time to prepare for these sessions, they were some of my favorite moments. Enterprise sales success involves many hands, and we made sure everyone’s efforts were appreciated and celebrated.

End the Year with a Big Celebration

After a year of hard work and change, we wanted to celebrate the entire team’s efforts. During SKO, we handed out over 50 trophies—taking inspiration from The Office’s Dundies Awards—to recognize the extraordinary contributions of our team members. (Picture below)

Final Thoughts: Building Community is an Investment

Creating a strong team culture requires time, energy, and focus. As a leader, you need to be intentional about making it a weekly priority. It’s about being on the frontlines, listening to feedback, and recognizing the great things happening within your team—not just once a year at SKO but regularly.

Building a community doesn't have to be expensive. Yes, we gave out awards and gift cards, but many times, it was a simple message, call, or public acknowledgment that made all the difference.

Unfortunately, many leaders and organizations don’t get this right — not out of neglect but because other priorities take over. It’s essential to be intentional about fostering community and culture throughout the year.

One last point: I had an incredible leadership team supporting me throughout this journey. They were fully engaged and committed to investing in building our community. While I set the initial idea and framework, their dedication was key to flawless execution. They took the vision, ran with it, and it was amazing to see how each team’s culture evolved, with every leader making a unique impact and contributing to its success!

These experiences inspired me to create the series "Igniting Sales Leadership," where I share lessons and strategies to support new leaders in similar situations.

"Culture eats strategy for breakfast" - Peter Drucker