Skip to content

Lead for the Long Game

By Joe Beutler, Amy Willard, Chris Blackburn, Michelle Gill, Ben Grinnell

A Guide for Disruptors and Their Enablers

In an era where AI capabilities advance monthly rather than yearly, mid-level enterprise leaders face an impossible choice: move fast and risk catastrophic failure, or move cautiously and become obsolete. This paper cuts through this false dilemma with a practical framework that lets directors, managers, and team leads modernize their organizations without sacrificing stability. Drawing from real-world case studies and battle-tested strategies from companies like OpenAI, John Deere, and GitLab, this guide shows how to raise both the floor and ceiling of organizational performance through deliberate disruption.

The paper centers on Elena’s transformation story—a newly minted IT director who navigates conflicting executive demands while building a bridge between bold AI vision and operational reality. Through seven core principles for strategic disruption, readers learn how to compress innovation cycles into 90-day sprints, create safe experimentation sandboxes, and build coalitions that turn skepticism into momentum. Rather than choosing between speed and safety, leaders discover how to make rapid adaptation a repeatable organizational capability that compounds over time.

This isn’t theoretical advice—it’s a step-by-step playbook for turning technological disruption from an existential threat into a renewable, competitive fuel. Whether you’re leading IT transformation, operations modernization, or cross-functional innovation initiatives, these principles provide the framework to modernize teams, secure executive buy-in, and position yourself as the architect of change rather than its casualty.

  • Format PDF
  • Pages 21
  • Publication Date September 16, 2025

Features

  • Disruption Framework

    Seven proven principles for navigating enterprise AI transformation safely.

  • 90-Day Cycles

    Compress innovation timelines without sacrificing operational stability or governance.

  • Coalition Building

    Turn organizational skeptics into change agents through strategic proof points.

  • Career Future-Proofing

    Position yourself as transformation leader while avoiding technological displacement.

About the Resource

In an era where AI capabilities advance monthly rather than yearly, mid-level enterprise leaders face an impossible choice: move fast and risk catastrophic failure, or move cautiously and become obsolete. This paper cuts through this false dilemma with a practical framework that lets directors, managers, and team leads modernize their organizations without sacrificing stability. Drawing from real-world case studies and battle-tested strategies from companies like OpenAI, John Deere, and GitLab, this guide shows how to raise both the floor and ceiling of organizational performance through deliberate disruption.

The paper centers on Elena’s transformation story—a newly minted IT director who navigates conflicting executive demands while building a bridge between bold AI vision and operational reality. Through seven core principles for strategic disruption, readers learn how to compress innovation cycles into 90-day sprints, create safe experimentation sandboxes, and build coalitions that turn skepticism into momentum. Rather than choosing between speed and safety, leaders discover how to make rapid adaptation a repeatable organizational capability that compounds over time.

This isn’t theoretical advice—it’s a step-by-step playbook for turning technological disruption from an existential threat into a renewable, competitive fuel. Whether you’re leading IT transformation, operations modernization, or cross-functional innovation initiatives, these principles provide the framework to modernize teams, secure executive buy-in, and position yourself as the architect of change rather than its casualty.

Joe Beutler
Amy Willard
Chris Blackburn
Michelle Gill
Ben Grinnell
Joe Beutler

Joe Beutler

Joe Beutler is a former software engineer who left Wall Street to start a food‑tech company, led customer success at a chat‑ops startup, architected global payments at Stripe, and now head the Solutions Engineering team for strategic accounts at OpenAI. When he’s not shipping multimodal AI demos, he’s grinding up East Bay single‑track or vibe coding side‑projects like Turtl, his one‑click photo enhancer for Airbnb hosts. Joe loves simplifying gnarly technical problems, coaching teams, and proving that a week‑off “hack‑cation” can change the roadmap.

To Author Archive
Amy Willard

Amy Willard

Amy Willard is an IT Director leading John Deere’s Agile Operating Model transformation. Amy has over twenty years of experience working in technology across multiple product segments and technology stacks. Her passion is helping John Deere transform how we work through focusing on Agility, Developer Experience, Technology Modernization, Quality, Technology Business Management, Product Management, and User Experience.

To Author Archive
Chris Blackburn

Chris Blackburn

Chris Blackburn is the CEO and founder of Liatrio, an AI-first technology consultancy that helps large enterprises modernize how they build, deliver, and operate software. He founded Liatrio with one clear goal: to help the largest and most complex organizations work smarter, faster, and more efficiently. He believes modernization starts with a people-first mindset, giving teams the clarity, skills, and systems they need to thrive in a fast-changing environment. Chris works with leaders who are ready to break old patterns, experiment boldly, and move with urgency.

To Author Archive
Michelle Gill

Michelle Gill

Michelle Gill is an accomplished technology leader with over twenty-five years in application development and more than a decade leading high-performing engineering teams. Her career has spanned diverse industries, including payments, medical, automotive, and education—where she discovered her passion for DevOps as VP of Linux Academy, a cloud-training platform which helped change lives by teaching DevOps practices. Since 2012, she has focused on building and scaling engineering organizations, where she experienced firsthand the transformative power of modern development practices. For the past six years, she has driven engineering excellence and organizational transformation at GitLab, a leading DevOps platform company, overseeing AI, ML, Data Science, Platform Engineering, and Feature Development teams.

To Author Archive
Ben Grinnell

Ben Grinnell

Ben Grinnell is Managing Director and Global Lead of the Technology and Digital Service Line at North Highland, where he has spent over twenty years specializing in digital transformation for large organizations across public and private sectors. With extensive experience in next-generation IT, DevOps, Agile, and Lean methodologies, Grinnell has led major technology initiatives spanning government, health, education, and transport industries. He previously served as interim IT Director at the UK Border Agency, where he built internal IT capabilities and restructured major outsourced contracts. Grinnell holds a BSc in Mathematics and Computing from Loughborough University, completed PhD-level research in predictive control algorithms, and currently serves as a Non-Executive Director at Decentenergy.io.

To Author Archive

Similar Resources