Think back to the Ice Age: humans didn't take down a mammoth with a spear. It took multiple hits, teamwork, and patience to guide the mammoth over the cliff. That's how milestones work, too.
This year has been full of them. They have shaped how I lead, set expectations, and build momentum for my team. As Q4 draws to a close and we close the last deals of the year, it’s a good time to reflect on the steps and small wins that got us here.
Last month I turned 50.. It's a big milestone, but I don't feel any anxiety about age. I still feel young in my mind, and that's what's more important than what's in my passport.
“How does it feel to be on the other side?” friends and colleagues ask. For me, it’s not about the number. It’s about what you do with your time. Life, to me, is about enriching other people’s lives.
As a sales leader, that's exactly what I focus on. I don't see myself as managing people. I enjoy helping others grow – whether it's supporting them, helping them become better salespeople, or just sharing experiences along the way.
Celebration of life
One of my biggest personal milestones this year was my 50th birthday celebration in Kenya. After my 40th birthday, I told my wife I wasn't going to have another big party. For years, I had a plan: the Inca Trail, the Galapagos, and Easter Island.
But last summer, on a sunbed in Kenya, my new home for a year-long remote adventure, I realized I wanted to share this place with my friends—many who had never been and might never have the chance. I invited many of my childhood friends to Kenya to experience this beautiful country together, and 47 came.
We arranged a tour of 25 camels on the beach, which turned out to be one of the most complicated tasks I've ever completed off. 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, went on a boat trip, saw dolphins, and snorkeled. In my speech, I said to my friends, “Some of you have been to Africa before, some of you have always dreamed of coming here, and some of you have had nightmares about traveling here.”
It was a celebration of life. We danced on tables, jumped fully clothed in the pool, and laughed all night. I could never have planned that feeling.
Share Milestones: Building a Generational Company
This year at Deel has been full of milestones. I see Deel becoming the kind of company that lasts for generations – one that people will recognize in years to come, like Oracle or IBM. We’re not just aiming for unicorn status with a $1 billion valuation. To me, a true unicorn is something rare and built to last, and I think Deel has what it takes.
Here are some of the milestones we have reached this year:
- Shift from a transaction-based, SMB-focused business to building strategic relationships with enterprise companies.
- Signing impressive “boast logos”, with more to come.
- Build a strong team culture and spirit.
These gains didn't come overnight. They've taken trust, perseverance, and the ability to pivot. Looking back at where we were a year ago, the progress is enormous. I'm especially proud to gain trust from organizations that are notoriously difficult to flirt with.
Like hunting a mammoth, these achievements were the result of many smaller, conscious efforts over time. They are the small wins along the way that make the major milestones possible.
Keeping the team motivated between wins
If we woke up every morning and all we did was drink the best champagne in the world, it wouldn't be as spectacular. In other words, you can't stay on top all the time because then that becomes your baseline.
I show my team that I am human – I have ups and downs, just like everyone else. Sharing my vulnerabilities helps create space for others to do the same. We all need to recharge in different ways. Some people do it through sports, others through travel, or simply by reading a book.
But while our feelings may change, our method does not. When we set a goal, we stick to it. The route may change, but the goal does not.
At Deel, we often talk about “Deel speed.” This isn’t about responding to emails quickly. It’s about iterating, failing quickly, and improving faster.
This approach has helped us create awareness and drive opportunities in areas where we didn't even exist a year ago.
It's a balance between fine-tuning and letting things happen. Adjusting our operational cadence to match our pace can create challenges. And managing expectations within the team at that speed isn't always easy.
3 lessons from the mammoth hunt
- Every effort counts, but every effort is not a direct hit. During the Ice Age, every spear counted, and everyone had a role. It’s the same in sales. Big wins are made up of small, methodical steps that get you closer to your goal. One of the first things I ask my team is, “Is there a timeline?” Managing that timeline often separates the great from the good. It also helps us manage expectations.
- Prioritize and focus on what is most important. At this time of year, the pressure is on. Sales are black and white – unlike other professions, like my wife’s work as a midwife, where success is not as easily measured. In sales, a signed contract on December 31st versus January 1st can mean the difference between night and day. I often remind my team, “This is how many days we have left in the year. Let’s make sure we focus on the right things. And don’t forget, we have next year too.”
- Collaboration and trust make the journey worthwhile. As I finish my third year at Deel, I see how these 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 worthwhile.
As Deel continues to grow, it is our ability to work together, trust each other, and recognize the milestones along the way that makes it possible to build something lasting. We all have different driving forces. Success is often about finding the mutual win.
Hunting a mammoth or closing a deal – none of them happen alone. Every spear thrown, every call made, every new piece of information about the prospect moves the group closer to the goal.
I'm excited about what happens next and look forward to seeing how far we can push the mammoth.
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