- From Developer to Fractional CTO
- A Mission That Aligns With Sustainable Growth
- AI in 2026: Implementation Over Hype
- The Real Roadblocks: Expectations and Change Management
- Bootstrapped and Strategic: Funding in Canada
- Advice for Founders: Technology is a Tool, Not the Goal
- Key Takeaways
- Listen to the Full Episode
In the latest episode of What the Tech from Boast, we sat down with Chris Ellefson, President and CTO of Ollon, a boutique agency specializing in custom software application development. Ollon works with teams to meet tight deadlines, strengthen their capacity, and rescue abandoned code, seamlessly integrating within organizations to fill skill gaps and extend in-house capabilities.
We've been fans of Chris and his team since we first connected in 2024, co-hosting and participating in pitch competitions for innovative businesses across Eastern Canada. Chris has served as a tech lead and mentor at organizations on both sides of the border, and his perspective on building sustainably in Canada's tech ecosystem offers valuable lessons for founders at every stage.
From Developer to Fractional CTO
Chris has been in the tech industry since graduating in the mid-1990s, starting as a software developer and moving up through technical architect and CTO roles at small startups. Around 2010, he noticed a gap in Toronto's startup ecosystem.
"At that point in time, the ecosystem in Toronto had a lot of what are called micro startups," Chris explains. "There was a need for fractional CTO work, and some opportunities came up. I ended up jumping ship from my full-time job and haven't looked back since."
What's a micro startup? Chris defines them as companies with two to five people (maybe one to three developers) who don't have the budget for a senior full-time CTO but still need strategic direction to make sure their development team is moving in the right way.
This fractional model became Ollon's foundation, providing flexible, specialized resources tailored to each client's needs without requiring the commitment of a full-time hire.
A Mission That Aligns With Sustainable Growth
There's a strong parallel between what Ollon does and how Boast approaches R&D tax credits. Both companies help teams access specialized expertise they wouldn't inherently find in-house, or can't afford to hire full-time today.
Ollon doesn't replace team members. They complement existing capabilities, filling skill gaps and extending capacity when resources are tight and every dollar counts. Whether it's meeting tight deadlines, modernizing development practices, or rescuing abandoned code, Ollon integrates seamlessly to help teams succeed.
This approach matters particularly in Canada's ecosystem, where bootstrapped companies and conservative funding environments make every strategic decision critical.
AI in 2026: Implementation Over Hype
When we recorded this episode in late 2025, AI was (and remains) everywhere. But Chris's perspective on how Ollon approaches AI work is refreshingly grounded.
What Ollon is working on:
- Helping companies implement AI solutions (integrating with large language models, document ingestion, creating customized RAG databases)
- Modernizing software development practices to incorporate AI tools that increase developer productivity
The key distinction: It's not just about building new AI products. It's about using AI as a tool to make product development seamless and leverage the best techniques available.
This aligns perfectly with what governments like Quebec are recognizing with programs like CDAE-IA; rewarding companies that integrate AI into their processes, not just those chasing buzzwords.
The Real Roadblocks: Expectations and Change Management
When we asked Chris about the biggest roadblocks companies face with AI implementation, his answer wasn't technical—it was cultural.
Roadblock #1: Unrealistic Expectations "One is expectations in terms of the idea that you'll have a turnkey AI solution that out of the box will all of a sudden magically fix things."
Roadblock #2: Change Management "It's more of a change management difficulty than it is a technical difficulty. There's a mindset shift that's needed and a process change that's needed."
For developers specifically, this means writing more documentation, spending more time prompting, and setting up structure for AI to write code. "That mind shift is difficult for quite a few people," Chris notes.
How to temper expectations: Chris emphasizes laying out what it actually looks like to roll out AI implementations—and that includes not just technology, but content and process. "If all you do is look at the technology, you're gonna end up with a lot of false starts and hallucinations from not having the right content in there."
This advice applies whether you're implementing AI tools or claiming R&D tax credits for AI integration work. The narrative matters. The process matters. The strategic thinking matters.
Bootstrapped and Strategic: Funding in Canada
Ollon has been bootstrapped since inception—never receiving VC funding. But they have leveraged government programs strategically:
- SR&ED tax credits for R&D work
- Co-op programs with government funding for partial student salaries
Chris's perspective on VC funding is nuanced, informed by watching many startup clients navigate that path: "Getting funding from VCs is a double-edged sword. They'll often push you faster than is natural for your business. I've seen various clients who, as a result of being pushed too fast, ended up not making it."
The Canadian difference: Chris notes the "general conservatism, fiscally, of the VC community" in Canada versus the US. While this can make subsequent funding rounds more challenging, it also encourages more sustainable growth patterns.
The strategic value of SR&ED: As we discussed, pursuing R&D tax credits isn't just about recovering costs—it's validation. When you qualify for SR&ED funding, you're demonstrating to the government (and potential investors) that your work is genuinely innovative, passes technical thresholds, and represents something net new.
This validation makes you more attractive to investors down the line and proves you're doing your due diligence as a business.
Ecosystem Over Everything
Throughout our conversation, Chris emphasized the importance of Canada's tech ecosystem and community partnerships. Ollon is:
- A member of PureScale
- Involved with True North CTO
- A mentor at Founders Boost
We've crossed paths with Chris and his colleague Susan at events like the Volta pitch competition (which we co-hosted), Code Launch Accelerator in Toronto, and through shared partnerships with organizations like Founders Better, BetaKit, and community leaders across Canada.
This ecosystem approach matters because it creates opportunities for collaboration, knowledge sharing, and mutual support—especially valuable in a more conservative funding environment where network and reputation carry significant weight.
Advice for Founders: Technology is a Tool, Not the Goal
When we asked Chris for advice for founders heading into 2026, his response cut through the noise:
"If you're a technology founder, technology is a tool for your business. There's a lot of bright shiny objects around now. It's important to take advantage of what AI brings to make your business more successful, but don't get caught up with the bright shiny objects. Really focus on how the technology can improve your business."
This echoes a consistent theme across our podcast: Don't build AI for AI's sake. Don't chase SaaS for SaaS's sake. Look for real value. Focus on what moves the needle and helps you build a sustainable business.
Technology should serve your business goals, not the other way around.
Key Takeaways
Fractional expertise fills critical gaps – Micro startups and growing companies often need strategic technical leadership but can't afford full-time senior hires. Fractional models provide flexibility and specialized skills.
AI implementation is change management – The biggest roadblocks aren't technical; they're about expectations, mindset shifts, and process changes. Lay out what implementation actually looks like—content and process alongside technology.
Bootstrapping has advantages – While VC funding provides capital, it can push companies faster than sustainable. Strategic use of government programs (SR&ED, co-op funding) offers validation and resources without giving up control.
Ecosystem matters in Canada – In a more conservative funding environment, relationships with accelerators, mentors, and community organizations create essential opportunities and support.
Don't chase shiny objects – Focus on how technology improves your business, not on implementing the latest trend because everyone else is. Strategic thinking beats hype every time.
Listen to the Full Episode
Want to hear more about Chris's journey from developer to fractional CTO, how Ollon helps teams implement AI without the hype, and why bootstrapping might be the right choice for your business?