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Lead Octalysis Consultant

Chris Tomasso

USA

Key Thematics

  • Complexity & Ambiguity Navigation
  • AI-Augmented Strategy
  • Organizational Sense-making

Regions Impacted

World map showing the regions where Chris Tomasso's work has had impact
Chris Tomasso

Featured Projects

Chris Tomasso

About Chris

“If you want to understand the outcome of a system, don’t tell me the intention. Show me the structure.”

Based in Seattle, Chris is a Senior Octalysis Lead Consultant focused on project sense-making, risk navigation, and behavioral system design. He works with teams to identify early signals of friction or failure and intervene while decisions are still inexpensive to change.

His expertise sits at the intersection of behavioral science, game design, and organizational dynamics, helping clients translate abstract strategy into forward momentum. He specializes in complex or ambiguous initiatives where alignment, decision-making, and stakeholder dynamics matter as much as execution.

Chris integrates AI as a collaborative thinking tool – using it to explore scenarios, surface hidden assumptions, and accelerate clarity. This allows teams to move faster without losing nuance or human judgment.

His work spans domains including marketing, healthcare, emerging technology, and AI adoption, with projects ranging from large-scale enterprise initiatives at companies like HTC, Microsoft, and Walgreens to experimental journeys in frontier technology spaces. With a background in film and digital media, Chris brings a strong storytelling lens to systems design, helping teams see not just what to do next, but why it matters.

The Octalysis Group

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Case studies

Measured results from our client work

See all 14 case studies

Hospitality

Hospitality Conversion Gamification

The Octalysis Group created a new industry standard for hospitality and travel booking platforms.

33.4%Increase in gross bookings

Loyalty

Gamified Loyalty Program

Gamified loyalty experience with personalized missions and rewards, leading to record-breaking engagement and conversions.

+153%Increase in credit card acquisitions

Fast-moving Consumer Goods

Sales Force Engagement

Gamified sales platform transforming reps into virtual traders, boosting engagement and performance across 19 countries. Best Gamification Award.

+28.6%Increase in sales revenue

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The Octalysis Group

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