[Top Agency Series] Building Your B2B SaaS Success Story With Chantelle Little of Tiller Digital

Chantelle Little is the Founder and CEO of Tiller Digital, a design and development agency helping B2B SaaS founders and marketers scale with conversion-focused web, brand, and product design. Under her leadership, Tiller has grown into a multi-million-dollar agency focusing on B2B software brands across Canada and the US. Chantelle’s dedication to her vision and her team has made her recognized as an Ernst & Young Entrepreneur of the Year finalist. At Tiller, she emphasizes a no-ego culture and the power of intergenerational cooperation, fostering innovation and mentorship among her diverse team. 

Here’s a glimpse of what you’ll learn:

• [03:44] Chantelle Little discusses how Tiller Digital started with explainer videos and evolved into a B2B SaaS-focused agency
• [06:56] Tiller’s brand narrative and design philosophy
• [08:38] The transformational impact of finding the right niche for your business
• [11:49] Chantelle talks about overcoming the challenges she faced as an entrepreneur
• [15:05] How dreaming bigger and recognizing limiting beliefs can propel personal and business growth
• [21:16] Tips for building a leadership team and culture
• [24:54] Leveraging an intergenerational team as a competitive advantage in the workplace
• [29:39] Chantelle’s recruitment and hiring process
• [32:54] Tiller’s customer success stories
• [39:32] B2B SaaS pricing strategies and best practices

In this episode…

Starting a business can be a treacherous path filled with financial constraints, relentless competition, and the daunting task of building a reliable team. Can a young entrepreneur navigate these waters and emerge victorious in the high-stakes world of B2B software agencies?

Thriving entrepreneur Chantelle Little delves into the intricacies of sparking agency growth, the benefits of focusing on a niche market, and the significance of intergenerational collaboration within her team. She shares how she transformed her passion for storytelling and web design into a thriving agency that serves B2B SaaS brands. She recalls early challenges, including financial struggles and the constraints of her limiting beliefs, and discusses the revolutionary mindset shift that resulted in dreaming bigger and achieving more. Chantelle also offers insights into strategic hires and the importance of a growth mindset in the hiring process.

In this episode of Inspired Insider Podcast, Dr. Jeremy Weisz interviews Chantelle Little, Founder and CEO of Tiller Digital, about building and growing a B2B SaaS-focused digital agency. Chantelle discusses how Tiller Digital started and evolved into a B2B SaaS-focused agency, the transformational impact of finding the right niche for your business, how dreaming bigger and recognizing limiting beliefs can propel personal and business growth, and tips for building a leadership team and culture.

Resources mentioned in this episode:

• Chantelle Little on LinkedIn
• Tiller Digital

Special Mention(s):

• Niche Down: How To Become Legendary By Being Different by Christopher Lochhead and Heather Clancy
• Die Empty: Unleash Your Best Work Every Day by Todd Henry
• Herding Tigers: Be the Leader That Creative People Need by Todd Henry
• The Accidental Creative: How to Be Brilliant at a Moment’s Notice by Todd Henry
• Agencynomics by Spencer Gallagher and Peter Hoole
• The Agency Secret: Proven Models to Transform & Scale the World’s Most Talented Agencies by Anthony Gindin

Related episode(s):

• “[Top Agency Series] Most Valuable Advice When Selling Your Agency With Todd Taskey of Potomac Business Capital” on the Inspired Insider Podcast
• “[Top Agency Series] Navigating a Merger and Becoming an End-to-End Digital Partner With Kevin Hourigan of Spinutech” on the Inspired Insider Podcast
• “[Top Agency Series] Growth Through Acquisitions – What is Your KPI and Northstar? With Jason Swenk” on the Inspired Insider Podcast
• “Building a Great Team and More Helpful Insights with Jason Swenk Host of The Smart Agency Master Class Podcast” on the Inspired Insider Podcast

Quotable Moments:

• “By finding the right niche, we’ve been able to really amplify our growth and tackle the unique challenges that B2B SaaS companies face.”
• “The key for me as a leader has been to recognize and move past my limiting beliefs, to achieve more for myself and my company.”
• “Bringing all those generations together in the workforce is like a superpower.”
• “Culture is key to building an intergenerational team, because it creates a space for everyone.”
• “My limiting beliefs about myself were holding back my whole company.”

Action Steps:

1. Identify and focus on a niche market: This approach allows specialization, leading to enhanced expertise and better client relationships within a specific sector.
2. Break through self-imposed limiting beliefs for personal and professional development: Overcoming limiting beliefs can unlock new levels of achievement and innovation.
3. Foster an inclusive culture and a growth mindset within your team: A culture of diversity and learning fuels creativity and helps to attract and retain top talent.
4. Implement intentional hiring practices: Fostering a team with the right attitude toward learning and development can increase adaptability and long-term success.
5. Utilize customer feedback to optimize the user experience on your digital platforms: Regularly assessing and adjusting based on user feedback ensures that the digital experience continues to meet and exceed customer needs.

Episode Transcript

Intro 0:01 

You are listening to Inspired Insider with your host, Dr Jeremy Weisz.

Jeremy Weisz 0:22 

Dr Jeremy Weisz here, founder of inspiredinsider.com, where I talk with inspirational entrepreneurs and leaders today, is no different. I have Chantelle Little of Tiller. You can find her at tillerdigital.com. And Chantelle, before I formally introduce you, I always like to point out other episodes of the podcast people should check out. Since this is part of the top agency series, a few of my favorites and fan favorites are Todd Taskey. Todd Taskey as a Second Bite Podcast, he pairs private equity with agencies. So he helps sell agencies second bite, because sometimes those agencies make more on the second bite than the first, because they sell the private equity. Private Equity sells again, and they have a nice payday there. So it’s a really good episode talking about the valuation space, the agency space.

Another good one was Kevin Hourigan of Spinutech. He’s at an agency since 1995 so it was really interesting to hear the landscape of the internet business and the agency space since then. Jason Swenk also was on talking about how he built his agency up to eight figures and sold it, and then he had been buying up agencies. So those have been interesting, really interesting episodes. And check out more on inspiredinsider.com. This episode is brought to you by Rise25. At Rise25 we help businesses give to and connect to their dream relationships and partnerships.

And how do we do that? We do that by helping you run your podcast. We’re an easy button for a company to launch and run a podcast. We do the strategy, the accountability and the full execution. So Chantelle kind of like what you do with the SaaS companies, we are the magic elves that run in the background and make it look easy for the host so they can create amazing content and amazing relationships. For me, the number one thing in my life is relationships. I’m always looking at ways to give to my best relationships, and I have found no better way, over the past decade, to profile the people and companies I most admire and share with the world what they’re working on. So if you’ve thought about podcasting, you should. If you have questions, you can go to rise25.com or email us at [email protected] I have a lot of free resources and podcast episodes about podcasting too. So check it out.

I am excited to introduce Chantelle Little. She’s the founder and CEO of Tiller. Tiller is a web and brand agency serving B2B software brands. She founded Tiller in 2008 at just 19 years old, right? You still look really young Chantelle. So she has scaled it to a multi-million dollar agency with clients across Canada and the US. She was named Ernst and Young Entrepreneur of the Year prairies finalist. It’s really impressive. I mean, that’s among the elite of elite, if anyone knows, like the Ernst and Young Entrepreneur of the Year awards, very difficult. So it’s pretty amazing what you’ve done there. So I’m excited to share what you do and your company with Tiller. So thanks for joining me.

Chantelle Little 3:23 

Thanks for having me. I really appreciate the opportunity.

Jeremy Weisz 3:26 

Let’s start off and just talk about Tiller and what you do. And as you do that, I’m going to pull up the tiller website. I mean, it’s only appropriate, because you help people with user experience web and everything in between, CRO, so I’m going to share it, but tell us about Tiller.

Chantelle Little 3:44 

Sure, yeah, thanks again for having me. At Tiller as you noted, we are a B2B software agents, or B2B software agency. We largely help clients out with web and branding work, but we also help out on the product side. We have a mix of clients that span from early-stage startup through the scale-up phase, up to the enterprise level, and we’ve been in business for, like you said, 16 years now. So love serving clients at various technical solutions and trying to help them articulate their message to the world and appeal to their target audience. So, and I have to say, We’re redesigning our website right now. So while you’re showing this off, it’s about to get way better.

Jeremy Weisz 4:31 

I love it. What I like to hear about is from the services side right now, you can see, obviously we’re on the site. Here you can see process, web brand, sales enablement, products, CRO, when you first started, a little bit of evolution of the services side. Where did you start? What was the service when you first started?

Chantelle Little 4:50 

It actually started with little explainer videos. So I was really — felt I had a summer job, really, that kind of gave me an opportunity to do this in the HR space, and I basically created these little paper people videos, is what I described them as. And took complex products and tried to break them down into simple stories and then use these paper cutouts and stop motion video to help articulate a story to HR managers. Did that as part of a summer job. That’s what inspired me. I loved the storytelling part of marketing, and that inspired me to start Tiller.

So started out with those videos, but it was six months later that I started to dabble on the website. Because, of course, we have YouTube and Vimeo and other things like that at the time. Now we have way more video platforms, but I felt like the website was a great place to have those videos live, so why not expand into the web? So from that point, web has been our primary bread and butter, and our clients have really been the reason that we’ve expanded beyond that into brand and sales enablement, CRO all those different pieces. So that’s kind of a bit of the evolution.

Jeremy Weisz 5:57 

So the web’s kind of the gateway drug to Tiller Digital.

Chantelle Little 6:01 

Yeah, exactly. You got it. You got it, yeah. And actually, it was pivotal in our niche focus towards serving B2B SaaS, because it’s so central, we have recently been calling the website the beating heart of B2B SaaS, right? Because there’s so much emphasis on the performance of the website in terms of customer acquisition as well as retention. So that has been what we have really built out. It’s kind of the hub in the middle of the wheel for Tiller in terms of service offering.

Jeremy Weisz 6:32 

I’ve had this, the website up in my browser, Chantelle all day. And it’s really interesting, because I have multiple screens here, and I’ll it will keep catching my eye because of these, movement of these almost like molecules. Can you talk about some of the decisions on the design on your website? Because I know you think these things through a lot.

Chantelle Little 6:56 

Yeah, absolutely. Yeah. Our brand narrative really starts with the name of the company, and that’s Tiller, of course, and we named the company after some people have the brand story of tilling the soil and growing things, and that’s one brand story. But another one is that a tiller, for those that don’t know, is actually attached to the rudder on a boat and is instrumental in steering a ship. So we really fell in love with that story because we believe that as our client’s agency partner, we’re helping them navigate new territory.

And so when we were thinking about how to bring that story to life visually, we wanted to tell a story of different landscapes, and we have this grid element that is used in the brand that kind of explains that there’s a pathway to get from point A to B, and then those shapes and those elements are essentially the moving parts. And we help clients, kind of guide them through different landscapes and help them navigate different territory. So that’s kind of the general storyline of it is navigation and direction and leadership.

Jeremy Weisz 8:04 

I love it. And so it’s almost like, for me, I was thinking, oh, it’s the subconscious is telling me to, like, scroll down the page because those molecules are moving. So I’m like, okay, I’ll do what the website is telling me.

Chantelle Little 8:17 

That directional design. So that’s a good, good catch. Yeah, there’s definitely ways to use design to help guide users through the journey, for sure.

Jeremy Weisz 8:26 

So the services side, I can see, yeah, talk about the niche part, yeah. And like when you first started out, what type of clients and now obviously specialize in B2B SaaS.

Chantelle Little 8:38 

Yeah, absolutely. So, my very first client was actually a pet food store, thanks to my uncle who helped me secure my first client back in the day at age 19. And so in the early days, we were the agency for all. I mean, we worked with clients in the oil and gas space, restaurants, retail, whatever it might be. It was very, very broad, and it was interesting, because I always liked the variety that that provided, but it became really challenging because all of those different industries and companies had varying needs, right?

We were serving like, B2C, B2B and then varying levels of sophistication and importance placed on the website. So I actually read a book called Niche Down one summer, and it talked about the concept of how it feels counterintuitive that if you niche down, it would be the very thing that would help you scale up. But that really stuck out to me, and I started to think more about that. And we in 2015 had started to work with some B2B SaaS companies out of Vancouver, and I’d really fallen in love with the unique challenges that B2B SaaS companies faced in terms of articulating their offering. For example, it’s usually quite complex, and how do you distill that and explain it in a simple way? How do you bring the values and the benefits to the forefront, instead of just talking about features. Those kinds of things.

And so I really fell in love with those challenges. Had quite a bit of experience. And in 2019 I read this book. 2020 we decided that we were going to actually take the leap and niche down, focusing on the B2B SaaS space, and start to not serve everybody and become the agency for B2B SaaS. And it was, on one hand, just wonderful timing for us, because doing that happened just before Covid, and while so many companies were impacted negatively by Covid, I think our decision to niche down at that time really led to a lot of our scale and our growth, because there was a ton of shift towards online tools and platforms and there was a need for the website became more and more central, right? So, we really helped companies with that. So yeah, we decided to niche down 2020 and we’ve been doing it ever since. Some of our clients have B2C audiences and B2G audiences, but primarily B to be focused.

Jeremy Weisz 11:01 

Was the book Niche Down or Niche Down Christopher Lockhead and Heather Clancy.

Chantelle Little 11:09 

You got it?

Jeremy Weisz 11:10 

Is this the book here? Yes, okay, yes. Cool. Love it. Actually, it’s funny, because I did have Chris on my podcast before, so people can check that out. And yeah, it’s a fantastic I thought that was the one, but yeah, people, check it out.

Chantelle Little 11:26 

Yeah, really good book.

Jeremy Weisz 11:27 

I love it. So I love hearing that journey for the services side, the evolution of, actually, the niche. I want to talk about sacrifice for a second, and talk about $30 a week, and what that means?

Chantelle Little 11:49 

Well, it’s been a tough road for me as an entrepreneur, and so early on, I started my business with some scholarship money, and I bought a MacBook Pro, and it was pretty low entry costs into the market. But I really struggled in my early years. And I think in part, I just lacked so much experience, and I was kind of, I’m kind of the school of hard knocks. So it got really tough for a season there, and I was struggling to keep the company afloat. And I mean, for the first eight or so years, the number of times I almost went bankrupt is more times than I can count, probably. It was just kind of waking up on Monday trying to figure out how I’d make payroll on Friday. And it was really, really tough. So I think you’re referring to my very lean grocery budgets and other things of that nature because I got creative.

I got creative with my banana and oatmeal eating the same thing every day, and just having to really budget personally and sacrifice a lot and not draw much money from the company really, just to survive all of that. And thankfully, along my journey, I was introduced to some folks, for example, hired a fractional CFO that helped me learn a lot about cash flow management and financial management, and that was instrumental, because at that point, it really helped me figure out how to scale Tiller without me having to figure out how to not eat. But it was super tough for many, many years, so I learned a lot about grit at that time and sacrifice for sure.

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