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Deborah O'Malley - Visionary Woman Founder to Watch — 2026
- Women Story
- Jan 12
- 3 min read
Category: Digital Marketing · Conversion Rate Optimization (CRO) · Experimentation & Analytics · UX + AI Strategy
Deborah O'Malley
Founder & Head of Product Strategy, GuessTheTest
📍 Based in: Ottawa, Canada
🌍 Global Reach: Worldwide (Digital Platform)
“Great growth doesn’t come from guessing — it comes from understanding how people really behave.”
In an era where businesses chase data but struggle to turn it into decisions, Deborah O’Malley stands out as a rare force — someone who blends behavioral psychology, experimentation, and ethics into scalable growth systems.
As the founder of GuessTheTest, Deborah has transformed how marketers, product teams, and growth leaders learn optimization. Her work demystifies A/B testing, challenges flawed industry assumptions, and replaces gut instinct with evidence-backed insight.
Recognised as a Visionary Woman Founder to Watch in 2026, Deborah represents the future of digital growth: human-first, data-driven, and rigorously honest.
Company Overview
Company Name: GuessTheTest
Founded: 2018
Industry: Digital Marketing · CRO · Experimentation Platforms
Headquarters: Ottawa, Canada
Website: www.GuessTheTest.com
What GuessTheTest Does:
GuessTheTest is a globally trusted experimentation and learning platform used by 10,000+ marketers and product teams. Through gamified A/B test case studies, AI-powered analysis tools, and in-depth resources, the platform helps teams understand what actually works — and why.
Instead of theory-heavy opinions, GuessTheTest delivers real-world test results, enabling faster, smarter, and more confident optimization decisions.
The Founder’s Vision
Deborah built GuessTheTest on a simple but powerful belief: most marketing decisions fail not because of lack of effort — but because of flawed assumptions.
Her vision centers on:
Turning user behavior into business breakthroughs
Removing bias from experimentation
Making CRO accessible, ethical, and statistically sound
Helping teams learn faster by studying proven patterns
With a background spanning UX research, AI-enhanced strategy, and behavioral analytics, Deborah brings academic rigor and real-world practicality into one cohesive system.
Why She’s One to Watch in 2026
Deborah O’Malley is recognised as a Visionary Woman Founder to Watch for her ability to:
✔️ Challenge outdated A/B testing practices with clarity and evidence
✔️ Scale a global learning platform reaching 21,000+ marketers
✔️ Combine UX, AI, and experimentation into ethical growth systems
✔️ Educate the next generation of leaders as an Adjunct Professor
✔️ Influence industry standards through research, teaching, and tools
Her work doesn’t just improve conversion rates — it elevates how decisions are made.
Key Achievements & Impact
Increased revenue and scaled a global subscriber base through GuessTheTest
Built an experimentation platform used by 10,000+ professionals worldwide
Achieved up to 35% conversion lift and 25% increase in LTV for client programs
Published peer-reviewed research and industry-leading CRO content
Launched a popular LinkedIn Learning course on marketing analytics and funnels
Taught product marketing analytics at Queen’s University’s Smith School of Business
Awards & Industry Recognition
🏆 Who’s Who in Experimentation Award — Winner
🏆 CRO Hall of Fame Award — Winner
🌍 Repeatedly listed among Top Global Optimization Influencers
🎓 Distinguished Faculty Teaching Award (2024)
Values & Leadership Philosophy
Deborah’s leadership is grounded in:
Ethical experimentation and privacy-aware analytics
Human-first technology and responsible AI use
Transparency in data interpretation
Education as a growth multiplier
Her work proves that integrity and performance are not opposites — they are partners.
The Road Ahead
As digital ecosystems evolve, Deborah is focused on:
Advancing AI-powered experimentation responsibly
Redefining CRO beyond simplistic A/B testing
Supporting mission-led brands at the intersection of tech, learning, and wellbeing
Building decision systems that respect users while scaling growth
Her journey reflects a larger shift in digital leadership — from tactics to thoughtful, evidence-based strategy.
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