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Letter from the Founder 2024
Read Chantelle Little's annual Letter from the Founder to find out what inspired Tiller’s “transformation year” and how she’s rallying the team around it
News
February 6, 2025
5 min read
Founder’s keynote presentation at Ambrose University
Returning to Ambrose University as a keynote speaker felt like stepping into a time capsule.
This was where my entrepreneurial journey began and where I first imagined what Tiller could become. Speaking to the next generation of business leaders, I wanted to share some of the lessons that shaped me, hard truths I discovered, and 16 years’ worth of trial-by-fire takeaways.
Here are a few of the lessons I shared, and why I think they’re just as relevant for seasoned B2B professionals as they are for new grads stepping into the world for the first time.
1. Your biggest barrier isn’t age or inexperience, it’s mindset
When I founded the agency that would later become Tiller, I didn’t know much about running a business. But I loved marketing and wanted to do it on my own terms. I was 19.
So, before I’d finished my degree at Ambrose, I applied for a home occupation license. I used my scholarship money to buy everything I needed to do the work (MacBook Pro, Final Cut Express, etc.). I set up my first “office” (it was my parents’ loft).
I was in business — as soon as I could rustle up my first client.
Looking back, I’m glad that I didn’t wait to graduate or stockpile experience. As a founder, nobody gives you permission to start. You give it to yourself when you take the initiative. If you’re waiting to feel ready, you’ll wait forever.
Start now, learn fast, and trust that you’ll grow into the role.
2. Resilience matters more than talent
My first project didn’t go well. I sold a video to a pet food store. They wanted a video for their retail location — something to show off some products and inject personality into the brand.
I invested way more hours than expected into that video (which means I severely underquoted, of course). But it was my first client, and I wanted to impress. I poured my heart into it.
Upon delivery, the owner watched my video in silence. He didn’t offer any feedback or criticism. He handed me an envelope of money, thanked me, and off I went. I got paid, so that’s a win, but I couldn’t shake the feeling that he’d hated it. And, sure enough, when I asked some friends to infiltrate the store later in the week, my video was nowhere to be seen.
The feeling that I’d let my first customer down was awful. But it was also a valuable lesson.
You’re not going to bat 100 every time. You’re not going to be a pro right away. Success takes grit — you need to put in the work today, tomorrow, and the day after that. Resilience matters more than losing sleep over the one deal out of a hundred that didn’t go to plan.
B2B SaaS founders need this same mindset. Product-market fit isn’t immediate. Sales cycles are long. Rejection is part of the process. What matters is how you respond.
So keep refining, keep improving, and keep pushing forward.
3. The right people make all the difference
I got used to being underestimated — and not just by prospects. I felt this acutely when it was time to move out of my parents’ loft. I met with a bunch of landlords who had small spaces listed on Kijiji for reasonable rates that fit my budget. But after that initial meeting, almost all of them seemed to undergo a sudden and inexplicable hike in rent (once by more than 50%!).
Maybe they thought my venture was too risky. Or maybe they didn’t want a kid like 21-year-old me renting from them.
The owners of the first space I leased were different. They treated me with respect and professionalism. They didn’t change the price or terms. Somehow, it felt like they believed in my vision — in me. And when it came time to upgrade to an office of my own, one of the owners of that first space found it for me. Their belief in me gave me the space (literally) to grow Tiller.
Surrounding yourself with the right people is empowering. This is a lesson I’ve learned and relearned as I build my team, connect with prospects, and grow my business.
In B2B SaaS, investors, customers, and partners won’t always see your vision. Some will hesitate. But the right ones will recognize your potential. Find them.
Surround yourself with people who challenge and believe in you.
4. The drive for excellence is a stand-out quality
It’s never been more tempting to take the easy road.
AI tools have empowered anyone with an internet connection to create something from nothing in less time than it takes to brew a cup of coffee. But the more I’m exposed to and experiment with AI, the more I think — wow, this is great for enhancing work (I used ChatGPT to outline this article). And wow, this is a terrible replacement for critical thinking and the human touch.
When we’re hiring talent at Tiller, we often receive 100+ applications for a role. And we’ve noticed an uptick in AI-generated cover letters, resumes, and emails.
(It’s amazing how everyone is now a [fill in the blank] professional with a strong background in [fill in the blank] and experience managing high-performing [fill in the blank]... you get the idea.)
But the real issue isn’t that they use AI, it’s that there’s no thought process behind it. It shows when short-listed candidates are interviewed or handed a role-specific assignment. The work quickly reveals whether or not they understand the subject matter.
The candidates we hire are the ones with a drive for excellence. They show up, demonstrate ownership, exhibit diligence, and deliver to target outcomes.
I think we feel this in SaaS too. Anyone can build anything now, but not everyone builds something excellent. Mediocrity is easy. Excellence demands much more.
Success doesn’t come from doing what’s easy, it comes from a relentless commitment to quality.
To sum it up
Growing a business isn’t just about revenue. It’s about impact. Whether you're just starting or scaling a SaaS company, commit to integrity, pursue excellence, and don’t wait for permission to chase your vision. I shared this lesson with Ambrose and I hope it resonates with you too.
