Luis Saffie

Luis Saffie

I've been a CTO, VP Engineering, and hands-on technology executive for 25 years.

I left my corporate C-level role to focus on the work that matters most: fixing what's broken and getting teams shipping again.

How I Got Here

I started as a software engineer in Chile, moved to Canada, and spent the next two decades building and scaling technology organizations. Amazon, Wealthsimple, HomeStars. Startups I built and sold. Every company had the same problems.

Tech debt crushing velocity. Teams that couldn't ship. Product and engineering speaking different languages. Founders watching their technical advantage slip away.

At Amazon, I built workforce optimization systems deployed across warehouses globally—systems that had to work flawlessly at massive scale. At Wealthsimple, I led infrastructure and security as the company scaled. At HomeStars, I was CTO through the acquisition.

Most recently I was contract VP of Engineering for AutoTrader's AutoSync software business, where I reorganized engineering around clear ownership, introduced estimation and roadmapping practices that unblocked a stalled e-commerce platform initiative, and led adoption of AI-assisted engineering workflows.

I learned that fixing these problems isn't about technology. It's about alignment. It's about getting product, engineering, and business speaking the same language. It's about building systems that don't break at 3am. It's about shipping the right things, fast.

After doing this inside companies for 25 years, I realized I could have more impact doing it for many companies at once.

What Drives Me

I get energized by solving hard technical problems, but what really drives me is seeing teams transform. Watching engineers go from burned out and shipping slowly to confident and moving fast. Seeing founders regain their technical advantage.

I'm obsessed with AI—not the hype, but the actual work of integrating it into products and operations. I've spent the last two years building companies with AI woven into everything. I've seen small teams move like companies 10x their size.

I'm also a co-founder of Heirly, a private platform for buying and selling established businesses. Every buyer, seller, and advisor is vetted before joining, and AI does the real work underneath—turning a focused set of strategic questions into structured profiles and listings, then curating matches on market data and stated intent. It keeps me building, not just advising, and it's where the AI practice I bring to client work gets pressure-tested.

I don't show up with a deck and disappear. I work alongside teams. I write code. I fix architecture. I sit in standups and planning. I do the actual work, because that's what moves the needle.

Beyond Work

I'm based in Toronto with my wife and two boys who keep me grounded. When I'm not fixing companies, I'm building things—home renovation projects, a backyard oasis with a pool and fireplace, tweaking guitar setups until they're perfect.

I bike, lift weights, BBQ obsessively, and take family trips. These keep me balanced and give me space to think through complex technical challenges away from the screen.

As a dad of two energetic boys, I've mastered the art of context-switching—debugging production issues while refereeing sibling wrestling matches. Turns out that skill transfers pretty well to managing multiple stakeholders in a crisis.

Background

Education

Computer Engineering, Universidad Andres Bello, Chile
Information Technology, York University, Toronto

Key Roles

  • • Contract VP Engineering, AutoTrader / AutoScout24 Group (AutoSync)
  • • CTO, HomeStars (led to acquisition)
  • • VP Engineering & Infrastructure, Wealthsimple
  • • Engineering Leader, Amazon (global warehouse optimization)
  • • Co-founder, Heirly (private business acquisition platform)
  • • Founder & CTO, multiple ventures (built and sold)

Focus Areas

Engineering leadership • Product strategy • AI implementation • Technical debt cleanup • Team scaling • Infrastructure & architecture

Let's Fix Your Team

If you're dealing with tech debt, slow shipping, or teams that can't align, let's talk. I've fixed this dozens of times.

Book 30 minutes and tell me what's broken. I'll tell you if I can help.

Book a Time

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Or email me directly at [email protected].