Remember the Ice Age: people didn’t fell a mammoth with a single spear. It took multiple strikes, teamwork, and patience to guide the mammoth off a cliff. Milestones work the same way.
This year has been full of them. Those milestones have shaped how I lead, set expectations, and build momentum in my team. As Q4 winds down and we close the last deals of the year, it’s a good time to reflect on the steps and small wins that brought us here.
Last month I turned 50. It’s a major milestone, but I feel no angst about age. I still feel young at heart, and that matters far more than the number in my passport.
“What’s it like on the other side?” friends and colleagues ask. For me, it’s not about the count. It’s about what you do with your time. Life, to me, is about enriching the lives of others.
As a sales leader, that’s exactly my focus. I don’t see my role as managing people. I enjoy helping others grow—supporting them, helping them become better sellers, or simply sharing experiences along the way.
Celebrating life
One of my biggest personal milestones this year was celebrating my 50th birthday in Kenya. After my 40th I told my wife I wouldn’t throw another big party. For years I’d imagined trips like the Inca Trail, the Galápagos, and Easter Island.
But last summer, lying on a sun lounger in Kenya—my temporary home during a year of distant adventures—I realized I wanted to share this place with friends, many of whom had never been and might never have the chance. I invited a lot of childhood friends to Kenya to experience this beautiful country together, and 47 came.
We organized a 25-camel ride on the beach, which turned out to be one of the most complicated tasks I’ve ever tackled. At one point I almost gave up. But after meeting someone in Amsterdam who connected me with the right people in Kenya, we made it happen.
We rented a 300,000-year-old cave for dinner and dancing, took a boat trip, watched dolphins, and went snorkeling. In my speech I told my friends: “Some of you have visited Africa before, some have always dreamed of coming, and some have had nightmares about traveling here.”
It became a celebration of life. We danced on tables, jumped fully clothed into the pool, and laughed all night. I could never have planned that feeling.
Deel milestones: Building a company for generations
This year at Deel has also been packed with milestones. I see Deel becoming a company that endures across generations—one people will still recognize years from now, like Oracle or IBM. We’re not only chasing unicorn valuation; to me a true unicorn is rare and built to last, and I believe Deel has what it takes.
Here are some of the milestones we reached this year:
- We shifted from a transactional, SMB-focused model to building strategic relationships with enterprise companies.
- We signed impressive marquee customers, with more on the horizon.
- We built a strong team culture and spirit.
These gains didn’t happen overnight. They required trust, persistence, and the ability to pivot. Looking back at where we were a year ago, the progress is significant. I’m especially proud that organizations known for being hard to woo have entrusted us.
Just like hunting a mammoth, these achievements are the result of many small, deliberate efforts over time. It’s the small wins along the way that make the big milestones possible.
Keeping the team motivated between wins
If we woke up every morning and all we did was drink the world’s best champagne, it wouldn’t feel as special. In other words, you can’t stay at peak constantly—otherwise peak becomes the baseline.
I show my team that I’m human—I have ups and downs like anyone. Sharing vulnerabilities creates space for others to do the same. We all recharge in different ways: some through sport, others through travel, or simply by reading a book.
Even if our emotions change, our method does not. When we set a goal, we stick to it. The route may change, but the objective does not.
At Deel we often talk about “Deel speed.” This isn’t about replying to email quickly. It’s about iterating, failing fast, and improving faster.
That approach has helped us build awareness and drive opportunities in areas where we didn’t even operate a year ago.
It’s a balance between fine-tuning and letting things find their shape. Adjusting our operational cadence to match our pace can create challenges, and managing expectations within the team at that pace isn’t always easy.
Three lessons from hunting mammoths
- Every effort counts, but not every effort is a direct hit. In the Ice Age every spear mattered, and everyone had a role. The same applies to sales. Big wins consist of small, methodical steps that move you closer to the goal. One of the first questions I ask my team is, “Is there a timeline?” Managing that timeline often separates great from good. It also helps us manage expectations.
- Prioritize and focus on what matters most. At this time of year the pressure is on. Sales is black and white—unlike other professions, such as my wife’s work as a midwife, where success is harder to quantify. In sales, a signed contract on December 31 versus January 1 can make all the difference. I often remind my team: “This is how many days we have left in the year. Let’s focus on the right things. And remember—we have next year too.”
- Collaboration and trust make the journey worthwhile. As I finish my third year at Deel, I see how those years have deepened my connections with the team. Celebrating wins together feels more meaningful because of the trust we’ve built along the way. For me, it’s the shared moments—whether with my team or friends in a Kenyan cave—that make the journey worth it.
As Deel continues to grow, our ability to work together, trust one another, and acknowledge milestones along the way enables us to build something lasting. We all have different drivers. Success often comes down to finding mutual benefit.
Hunting a mammoth or closing a deal—neither happens alone. Every spear thrown, every call made, every piece of new information about a prospect moves the group closer to the goal.
I’m excited for what’s next and look forward to seeing how far we can drive the mammoth.