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How to Implement a Successful Pilot Program for Digital Transformation

A practical framework to design, execute, and scale pilot programs that validate technology, build confidence, and drive measurable business outcomes.

digital transformation

According to McKinsey, nearly 70% of digital transformation initiatives fail to meet their goals despite record spending and rapid advances in technology. Gartner reports that by 2026, over 80% of organizations will have tried some form of automation or AI-led transformation, yet fewer than 30% will successfully scale beyond the pilot stage.

The problem isn’t technology, it’s how companies start.
Too many pilots are rushed, vendor-led, or poorly aligned with business outcomes. Others linger in “pilot purgatory,” where initiatives consume time and budget without producing measurable results.

This whitepaper provides a practical, data-backed framework for running pilot programs that work. You’ll learn how to design pilots that validate technology, generate stakeholder confidence, and create a seamless bridge from experimentation to full-scale implementation, helping your business move from testing potential to proving value.

Who should read this

  • CIOs, CTOs, and transformation leaders leading modernization initiatives
  • Business executives planning digital investments or process overhauls
  • Innovation and IT teams designing pilot programs and testing frameworks
  • Decision-makers seeking a low-risk, high-impact path to scale new technology

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joel cumming
Joel Cumming CTO, Skywatch