Deborah O’Malley Is Building a Calmer, Smarter Way to Grow Digital Products

Women Story
Feb 2
2 min read

Most growth decisions don’t fail because teams lack data. They fail because too much confidence is placed in the wrong signals. Deborah O'Malley has spent more than a decade watching this pattern repeat — and quietly building an alternative.

Based in Ottawa, Canada, O’Malley is the founder of GuessTheTest, a global experimentation and conversion optimization platform that helps teams test ideas without ego, bias, or unnecessary complexity. Since launching in 2018, the platform has grown into a trusted resource for over 21,000 marketers and product leaders worldwide.

From Curiosity to Conviction

O’Malley’s career has been shaped by a simple question: why do people behave differently than we expect? With formal training in behavioral psychology and eye-tracking research, she learned early that intuition often misleads — especially in digital environments.

After years advising SaaS and e-commerce brands on conversion strategy, she noticed a recurring problem. Teams wanted to experiment, but lacked frameworks they could trust. Too many decisions were driven by opinion disguised as insight.

GuessTheTest was created to change that.

Making Experimentation Human

Rather than building another analytics tool, O’Malley designed GuessTheTest as a learning platform. Real A/B test case studies are presented in a gamified format, inviting users to predict outcomes before revealing what actually worked — and why.

The result is deceptively simple and quietly powerful. Each test published on the platform meets strict methodological standards. There is no vendor bias and no exaggerated claims. Only evidence.

“Good experimentation isn’t about proving you’re right,” O’Malley has said. “It’s about being willing to learn when you’re wrong — and designing systems that make that safe.”

Growth Without the Spotlight

GuessTheTest has grown steadily while remaining intentionally small, operating with a lean team of fewer than ten people. The company has increased revenue and subscriptions without chasing scale for its own sake.

That restraint has earned O’Malley peer-driven recognition, including the Who’s Who in Experimentation Award and the CRO Hall of Fame Award — honors that reflect influence, not visibility.

Alongside building her company, she serves as an Adjunct Professor of Product Marketing Analytics at Smith School of Business at Queen’s University, where she received the Distinguished Faculty Teaching Award. Her work as an educator reinforces a core belief: clarity is a leadership skill.

A Grounded Perspective on AI

As AI reshapes experimentation, O’Malley remains measured. She views technology as a support system — not a substitute — for human judgment. In her work, AI accelerates insight, but ethics and context remain central.

Today, she is increasingly focused on partnering with mission-led organizations working at the intersection of technology, learning, and wellbeing — companies building products with long-term impact in mind.

For O’Malley, sustainable growth is not about running more tests. It is about asking better questions, listening carefully, and resisting the pressure to move faster than understanding allows.

In a field often driven by certainty, her strength lies in something quieter: intellectual humility — and the discipline to let evidence lead.