Chantelle Little: Breaking Barriers in Business and Creativity

Chantelle Little is the Founder and CEO of Tiller, a Calgary-based digital marketing agency serving B2B software brands across North America. At just 19, while still pursuing her business degree, Chantelle launched Tiller - and has since grown it into a multi-million-dollar agency known for its creativity, strategy, and impact.

Talent CHANTELLE LITTLE / Photography by IHOR SAVELIEV / Makeup ANASTASIIA SAVELIEVA

With expertise in strategic business development, team leadership, and fostering thriving workplace cultures, Chantelle has become a powerful advocate for Canada’s tech and entrepreneurial communities. In Calgary, she inspires and empowers young designers and entrepreneurs through her role as City Champion for Lemonade Day - a program that gives kids the confidence and tools to start their first business.

Talent CHANTELLE LITTLE / Photography by IHOR SAVELIEV / Makeup ANASTASIIA SAVELIEVA

An alumna of Ambrose University with a Bachelor’s in Business Administration, Chantelle was recognized as an EY Entrepreneur of the Year Prairies Finalist in 2018 and one of Avenue Magazine’s Top 40 Under 40 in 2023. Guided by her personal motto, No Ceilings, she continues to inspire others to break through barriers and create without limits.

Talent CHANTELLE LITTLE / Photography by IHOR SAVELIEV / Makeup ANASTASIIA SAVELIEVA

Beyond her professional achievements, Chantelle is known for her down-to-earth and tenacious spirit. She finds inspiration from design everywhere, and has a special passion for architectural, interior, and graphic design through history.

HASEL Magazine: Chantelle, welcome — it’s a joy to have you with us! You founded Tiller at just 19 - in an industry and at a stage of life where many might hesitate. What gave you the courage to start, and what advice would you give your 19-year-old self today?

Naivety is bliss, right? When I started Tiller, I didn’t really see launching a company as a courageous act. It felt exciting. It felt natural. In many ways, I didn’t have much to lose other than the scholarship money I used to start my company. That said, my courage was tested and cultivated every day since. And I’m quite confident that will never stop.

People love to ask me, “Would you recommend starting a company that young?” The reality is that there are pros and cons. Statistically, data shows that entrepreneurs with more life experience are more likely to succeed. In my case, I was learning how to become an adult version of myself while also learning how to run a company. I noticed that as I gained confidence in my own skin and matured, it translated into more business success. At times, I was discouraged by the slow and steady progress. But I’ve learned that’s not a bad thing. Slow and steady can lead to sustainable success. So, if I had to give my 19-year-old self some advice, I’d probably say, “You’re running a marathon, not a sprint.” The media praises the so-called overnight successes. For years, I felt really behind. But I’ve learned that there is no such thing as an overnight success. Behind every success is a lot of blood, sweat, tears, and perseverance.

Talent CHANTELLE LITTLE / Photography by IHOR SAVELIEV / Makeup ANASTASIIA SAVELIEVA

HASEL Magazine: In your childhood, you showed an entrepreneurial spirit by selling lemonade and even publishing your own newspaper. How did these early hobbies and experiences influence your decision to found Tiller, and what do you think adult entrepreneurs can learn from children, who approach life with curiosity and openness?

Hindsight is 20/20. When I was a kid selling pop cans on the 15th hole, publishing newspapers, hosting a community-wide production of Cinderella, and starting an extra-curricular baseball league (because playing baseball 3 days a week wasn’t already enough) I had no clue this was an indication I’d fall in love with entrepreneurship. When I was in grade 5 I penned an autobiography for a school project, and boldly proclaimed I’d be an engineer and work in oil and gas. But all these years later, looking back, I see all the signs that I’d fall in love with entrepreneurship. As I grew and matured, I learned more about how I’m wired as a person and realized that nothing excites me more than building something from nothing.

I believe that kids are born with an extraordinary amount of curiosity and wonder. Somewhere along the line, life challenges and often stifles both. It could be rejection, failure, others’ opinions, insecurity, comparison, and the list goes on and on. I believe that the most successful entrepreneurs find a way to protect and continually cultivate that childlike curiosity and wonder for themselves and their companies. Someday I want to be the 80-year-old who still has that childlike wonder in my eyes. 

Talent CHANTELLE LITTLE / Photography by IHOR SAVELIEV / Makeup ANASTASIIA SAVELIEVA

HASEL Magazine: Your motto, No Ceilings, suggests limitless growth and vision. Was there a particular moment in your career when you realized what that phrase meant to you personally?

I hired an Executive Coach to help me develop as a leader. She tasked me with a homework assignment: write down every limiting belief you have about yourself or your company with your non-dominant hand. Later that evening, I grabbed a coffee and sat on my couch with a notebook and got started. 67 limiting beliefs later and a few shed tears, I finally got the assignment. I’m a fast-moving person and I don’t take handwritten notes very often, let alone with my non-dominant hand. As I attempted to write out 67 limiting beliefs with my left hand, I was forced to slow right down and see how silly these limiting beliefs really were. The tears? They came because it was during this homework session that I realized that my own personal limiting beliefs were holding my entire company back. I wanted my team to grow and win! It’s crazy how much a leader's own mindset can influence the course of their organization. It was following this personal breakthrough, where I developed the motto “No Ceilings” and it’s stuck with me ever since. Today, I can look back at Tiller’s history and correlate this mindset shift with a huge shift in the company’s growth trajectory. It helped me dream bigger for Tiller, and invite my team to do the same.

On a personal note, that mindset shift has also led to personal growth outside my work, too. Tired of short-sighted new years resolutions, one January I took the approach of asking myself, “What am I truly capable of?” And this single question (and a ton of grit to follow), helped me change my lifestyle (better nutrition, better sleep, a consistent workout routine) and drop 35 pounds. This is significant because prior to this change, I’d grown to believe I could never be in shape while also managing a very demanding career and life. Fast forward to today and I now see that change in lifestyle as being the very thing that enables me to manage my demands. It’s crazy how the narratives we tell ourselves can be the very thing holding us back from change. 

Talent CHANTELLE LITTLE / Photography by IHOR SAVELIEV / Makeup ANASTASIIA SAVELIEVA

HASEL Magazine: You’ve grown Tiller into a multi-million-dollar agency serving clients across North America — but what does ‘success’ look like to you now? Has that definition changed over the years?

For me, success has always been about character and impact. Along the way, Tiller’s sphere of influence has significantly grown. With that, it’s challenged me to dream bigger about what impact we (as Tiller) and I (as a person and leader) want to make in this world. So my vision has definitely grown and is very multi-faceted.

From a business perspective, we have a global vision for Tiller and we’re working hard day in and day out to realize that vision. To get there, we’re planning to scale our revenue, team, services, and much more. We want to help more B2B software companies win.

From a personal perspective, success to me is quite simple. I want to live out my faith in a real and authentic way. And I want to be a present and loyal daughter, sister, auntie (one of my all-time favourite roles in life), and friend. My family and friends have impacted me more than words can describe, and I want to spend my life finding ways to give back to them. Philanthropy is also near and dear to my heart, and I look forward to continuing to engage with the community to increase impact. Ultimately for me: success isn’t about what you get, it’s about what you give.

Talent CHANTELLE LITTLE / Photography by IHOR SAVELIEV / Makeup ANASTASIIA SAVELIEVA

HASEL Magazine: You’ve supported Calgary’s entrepreneurial communities through Lemonade Day. Why is fostering the next generation of creatives and founders so important to you?

While I had many entrepreneurial-like experiences as a kid, I didn’t really know entrepreneurship was a viable career path for me. It took until university for me to really understand the possibilities and I dove right in. This is one of the reasons I find great fulfillment in introducing the next generation to entrepreneurship. Lemonade Day isn’t just about setting up a lemonade stand. The curriculum helps teach kids the basics of business and financial literacy. We’re in our 3rd year running the program in Calgary and the stage is set for our biggest year yet - and as of writing this, we have 1,000+ kids set to host lemonade stands across the city on Sat, July 19th. Whether kids go on to be entrepreneurs or pursue other career paths, I hope the experience teaches them a lot about themselves, about working with others, and helps them dream a little bit bigger than they did before.

Talent CHANTELLE LITTLE / Photography by IHOR SAVELIEV / Makeup ANASTASIIA SAVELIEVA

HASEL Magazine: What is one piece of advice you would share with aspiring entrepreneurs who are looking to carve out their own path in the business world today?

We all are inundated with stories and narratives of people who build thriving side gigs or scaling empires. Sometimes without meaning to, we find ourselves aspiring to write a story we’ve seen before. But pursuing someone else's story undermines our unique strengths, passions, and point of view. We’re all wired differently. In a world of constant comparison, it’s easy to see that as a bad thing. But comparison is the killer of joy. Instead of fixating on what other people are doing or achieving, my advice is to get busy doing what you were made to do. And on that journey, become as comfortable with looking at your gaps as you are celebrating your wins. You’ll learn a ton about yourself, and if you’re willing to face those gaps head on you’ll reinvent yourself over and over again. Write the story that is uniquely yours.

HASEL Magazine: Thank you, Chantelle, for such an open and inspiring conversation. Your experiences offer so much to learn from, and we’re grateful you shared them with us.

If you’d like to learn more about this amazing digital company and about Chantelle, just follow the link.