Darby Sieben
About

Thirty years in tech, and still happiest with a hard problem and an ambitious team.

The short version: I've built and run companies, and these days I work for myself — helping teams grow through product and partnerships, navigate transformation and put AI to work.

I grew up on a farm in Saskatchewan. My parents would never have called themselves entrepreneurs — they worked hard to provide: farming, then a trucking company and a bra business after we moved to the city. I learned early what a wasted dollar costs a family, and thirty years later that's still how I treat other people's money and time.

My edge is pattern recognition: I've led the product, the deals and eventually the entire company, owned the P&L and now invest — so I connect dots across the whole business that most people miss. I'm direct, I move fast and do my best work in a t-shirt and hat, not a suit and tie.

The path

Now
Independent advisor & investor — growth, transformation, AI-first strategy.
Unbounce
Chief Product Officer.
RBC
Launched a venture (Ampli Cashback) with Canada's largest bank.
Yellow Pages Group
Senior executive — Corporate Strategy & Partnerships.
Mediative
President of the $50M/year digital agency.
SkyMotion
My first angel investment — acquired by AccuWeather.
Yellow Pages Group
Sold my company to YPG; led product and partnerships.
KS Solutions Inc.
Founded and ran my search agency — acquired by Yellow Pages Group.
City skyline at dusk
The underrated chapter

Yellow Pages was at the forefront of web, search, cloud and APIs — before most companies knew they needed it.

The logo wasn't sexy. The work was.

In the community

You can't win a gold medal without a coach. I had great ones — this is me being one.

Platform Calgary
Investor coach to early-stage founders & incubator board member.
Venture Mentoring Service of Alberta
Volunteer venture mentor to scale-up founders. Their philosophy, and mine: don't build the race car — train the driver.
Investing

Some of my recent angel investments.

Walnut Insurance Quickly Technologies Boardy.ai

Earlier bets include SkyMotion (acquired by AccuWeather) and WFHomie (acquired by GoCo).

Beyond the work

Some of the work that matters most isn't paid.

Every year I walk — and fundraise — in the Gutsy Walk, Crohn's and Colitis Canada's flagship annual event. Since 2021 I've raised over $32,000 for the cause, one of Calgary's top fundraisers. It's personal, it's stubborn and it's a reminder that the same persistence that builds companies can move things that actually matter.

A personal note

The hardest leadership challenge of my life wasn't in a boardroom.

It was my father's dementia. Walking through it taught me things about patience, presence and leading without a clean answer — and they turned out to be unmistakably professional. I wrote about it, because I think more of us are quietly carrying something similar.

Read: When Leadership Became Personal →

More on LinkedIn.

I share what I'm thinking and building. Follow along, or reach out directly.