News Tiller

December 22, 2025

6 min read

Letter from the Founder 2025

Chantelle Little, Founder of Tiller, on her laptop at a coffee shop

Chantelle Little

Founder & CEO

“You’re not dreaming big enough.”

That’s what my executive coach, Ryan, said to me earlier this year.

“What would thrill you?” he asked. “Like, actually thrill you to achieve with Tiller?”

I remember laughing a little when he said it. I don’t often get told I’m not dreaming big enough. Usually it’s the opposite: that I’m dreaming too big, moving too fast, or need to slow down.

But I took a moment and really thought about it. When I answered and described the vision I carry deep down for this company and this team, I felt it in my body. Goosebumps. Energy. That mix of excitement and fear that usually means you’ve told the real truth.

“Now we’re talking,” Ryan said. “So, as the CEO, who do you have to become in order to make that vision a reality?”

That question is redefining how I lead.

What I realized in that moment was uncomfortable and clarifying: the ceiling on Tiller’s growth is directly connected to my own willingness to grow as a leader. And if I’m not willing to do the hard, often invisible work of leadership, the vision will never become reality.

As I look back on this year, leadership is the theme that stands out most, and I don’t think we talk about it enough.

There are countless books, frameworks, and playbooks about improving organizational performance. As leaders, we spend hours upon hours in meetings talking about how to get better outcomes.

There are far fewer conversations about developing the leader themselves. We’re often quick to look outward for improvement… new tools, new processes, new systems, new AI… hoping they’ll unlock the next level of performance. And those things do matter. But this year reminded me how easy it is to invest in everything around people, while underinvesting in the people themselves.

This year, I spent time in a lot of rooms with marketing leaders: Austin, New York, Washington D.C., and a handful of places in between. Different companies. Different stages. Different audiences.

But the same pattern kept surfacing.

The GTM playbooks that got us here are breaking down.

Some of that is being accelerated by AI. Some by market saturation. Some by shifting buyer behavior, shrinking budgets, and the relentless pressure to do more with less. Whatever the cause, the result is the same: leaders are being asked to navigate a level of change that doesn’t come with clear answers.

It made me realize something important: when the external playbook breaks, vision becomes even more critical.

A clear, compelling vision creates direction when there’s no obvious path. As my coach has helped me frame it: the vision is the boss. Decisions become easier because everything is measured against the vision. Does this support the vision, or distract from it? Teams stop waiting for permission and start moving with intent.

But there’s a catch.

Once you’re clear on where you’re going, you’re forced to confront the gap between where you are now and where you need to be. And that’s the part most of us avoid.

Looking honestly at that gap means taking a hard look in the mirror and acknowledging where you need to grow. Patterns that once served you may now limit you. Ways of leading that worked at one stage of growth won’t be effective in the next.

I’ve built Tiller by doing. I’m comfortable executing. For a long time, leadership felt like something I did alongside the real work. This year, that changed.

Leadership is the work.

Not the thing you do when you have time. Not on the side of your desk. The job itself.

And for me, stepping into that fully has meant spending less time jumping in to solve and more time creating clarity, setting direction, and developing the people around me.

That shift sounds simple. It isn’t.

Leadership asks you to give up some of the things that once made you feel most valuable — being the fixer and the one with the answers — and replace them with restraint and helping others level up. It asks you to stop proving your value through output and start proving it through outcomes you don’t directly own.

Earlier this Fall, that lesson became very real for me.

We ran an internal pitch fest at Tiller to surface new ideas that could unlock new value for our clients. From there, we took the strongest idea and turned it into a full-day hackathon, bringing the entire team together to go from concept to something tangible in a single day.

I had a vision for the hackathon and invested my energy in setting the stage for the day (defining success, creating constraints, establishing structure, etc.).

And then, when the day arrived, I made a deliberate choice to lead and stay out of execution.

All day, a quiet voice followed me around:

You’re not contributing. You’re not doing enough. You should jump in and help more.

But I didn’t. And by the end of the day, that voice was gone. I realized that by staying in a place of leadership, I had created the space for my team to solve big problems and unleash their creativity at a level that surprised us all.

It was a clear picture of what vision-led leadership looks like in practice. My role that day wasn’t to be a do-er. It was to create the conditions where others could explore what they are capable of and let them deliver.

My coach and I now call that version of me “Hackathon Chantelle.” Not the version that jumps in to solve, but the version that prepares, trusts, and empowers my team.

A related sidenote: This year, I reconnected with my childhood love of basketball. I’ve been following the WNBA closely and one player in particular, Paige Bueckers, one of the league’s newest stars.

In a recent interview, she talked about how her coach helped her realize that her team’s performance was directly tied to her own growth as a leader. Not her talent. Not her effort.

What struck me was that her growth didn’t mean doing more. It meant showing up differently and intentionally involving everyone on the court. Her development expanded the team’s ceiling without changing the roster. And that team won the 2025 NCAA National Championship.

Instead of the leader having an impressive individual performance, the leader calls everyone forward. That’s the difference between incremental progress and exponential growth.

There’s a quote I love: “In the video game of life, everyone has a next level and no one gets there by themselves.” (Jason Jaggard, Novus Global)

That captures 2025 perfectly for me. Game changing leadership means putting in the work to become the leader the vision demands and intentionally helping everyone around you do the same.

As we look ahead to 2026, I invite you to join me in slowing down and reflecting on three key areas of leadership:

First: vision.

Paint a really clear picture of the vision you want to achieve in 2026. Then pause and ask, like my coach did, does it really thrill you? Does it energize you and feel impossible at the same time? If so, you’re probably on to something.

Second: the gap.

Now ask yourself these sobering questions: What’s the true gap between where you are today and where you want to be? Where might you be getting in your own way? What are you tolerating that’s holding you back from the vision? A lesson I learned this year is that a person’s capacity for growth is directly linked to how much truth they can face about themselves without running away.

Third: strategy.

Now that you know what the gap is, strategy is the tool you use to close it. My coach has helped me adopt a new definition of strategy: Strategy is a hypothesis about how you’re going to win on a playing field of your choice. Seeing strategy as experimentation takes some heat off. You don’t have to figure it all out at once. What’s one leadership experiment you could run in Q1 to take your team to the next level?

There are no right answers. But I’ve found sitting with these questions has changed how I show up for myself and the people I’m leading.