Leadership for bold moves & the hyper-digital era

Keynotes and Workshops for Your Company, Your Culture, Your Industry. Designed specifically for the mission of growth, innovation & transformation.

Change the status quo of your business and the way you work.

By early Amazon executive, Gates Foundation and T-Mobile advisor, & author of the best-selling leadership books The Amazon Way & Big Bet Leadership

John is a former Amazon Executive, Advisor to the Gates Foundation & T-Mobile, 4x Best-Selling Author, and Leading Innovation Speaker.

John Rossman is renowned as an early Amazon executive who led the launch and scaling of the Amazon Marketplace. He has served as a Senior Technology Advisor at the Bill and Melinda Gates Foundation and a Senior Innovation Advisor at T-Mobile. He has a unique and powerful range of expertise in leadership for innovation, strategy for Artificial Intelligence and disruptive technologies, high-performance teams, and culture.

John has authored four best-selling books on leadership, strategy, and disruptive technologies, including The Amazon Way and Big Bet Leadership. These works provide principles, frameworks, and tactics for developing management to lead digital and AI-first companies that customers and investors love and are purposefully designed for a sustainable competitive edge and advantage. 

John delivers motivational speeches and workshops on leadership, team culture, business results, and playbooks for immediate action. His expertise is in leadership for digital transformation, artificial intelligence & innovation, and leading high-performance teams.


John Rossman
Digital and Innovation Keynote Speaker
Author | Advisor | Founder

Signature Keynotes on Digital Transformation, AI, Innovation and High-Performance Teams


Winning with Artificial Intelligence — Innovation and Execution in the Hyper-Digital Era

John Rossman’s latest keynote, “Winning with Artificial Intelligence—Innovation and Execution in the Hyper-Digital Era,” dives into AI’s transformative potential within the business world and explores how leaders can guide significant transformations in organizations through the strategic adoption of AI technologies.

Rossman forecasts the hyper-digital era—a time characterized by rapid technological evolutions where artificial intelligence reshapes the fundamentals of industries, economies, and societal structures. He discusses how AI can serve as a transformative force, offering unprecedented efficiencies, capabilities, and insights. This section illuminates AI’s integral role in achieving high velocity in decision-making and operational agility, underpinned by robust case studies and empirical data.

Rossman introduces attendees to actionable frameworks for embedding AI into core business strategies. The keynote delves into the methodologies for identifying AI opportunities, data architecture optimization, and fostering a culture conducive to digital and AI-centric innovations. Emphasis will be placed on “Strategic Innovation Execution,” which leverages AI for not only incremental improvements but also for groundbreaking business models and products that can redefine marketplaces.

The keynote’s culmination focuses on the practical aspects of executing AI strategies within diverse organizational contexts. Rossman addresses common execution challenges—from technical integration hurdles to ethical considerations—and how to overcome them. By exploring successful case studies, he provides a nuanced understanding of how different industries can harness AI’s potential responsibly and effectively. Attendees leave with a clear set of strategies for implementing AI solutions that align with their strategic objectives and create sustainable competitive advantages.

Leaving Your Audience with:

  • Strategic Roadmaps: Clear methodologies and frameworks for integrating AI that align with their business models and market dynamics.
  • Innovation Playbook: Actionable insights on navigating the digital transformation with AI, turning technological potential into market-leading innovations.
  • Cultural Transformation: Guidelines for cultivating an organizational culture that embraces AI and drives innovation through its adoption.
  • Ethical Compass: Understanding of the ethical implications of AI deployment and strategies to address these concerns proactively.
  • Competitive Edge: Tools and case studies demonstrating how to leverage AI for sustainable competitive advantages, ensuring long-term success in the hyper-digital era.

Leadership and Culture for Innovation and Bold Moves  – The Amazon Way

John Rossman offers a dynamic exploration of the leadership and cultural frameworks cementing Amazon as a paragon of innovation, grit, and audacious corporate strategies. This popular presentation synthesizes lessons from Rossman’s books to deliver a comprehensive guide for cultivating a culture that embraces innovation and drives it at every level.

Rossman begins by dissecting the foundational elements of Amazon’s leadership philosophy as detailed in “The Amazon Way.” He explains how Amazon’s leadership principles are designed to foster a culture of high standards, ownership, and relentless focus on customer outcomes. These principles are not just theories but practical tools that Amazon leaders use daily to make decisions and inspire teams. The audience will learn to apply these principles to create a leadership environment that encourages bold thinking and meticulous execution.

Building on this foundation, Rossman delves into “Think Like Amazon: 50 1/2 Ideas to Become a Digital Leader,” providing actionable strategies for embedding innovation into an organization’s DNA. He highlights how continuous innovation cycles and a willingness to experiment can be instituted across various business functions to disrupt industry norms and redefine service delivery. Through engaging anecdotes and empirical evidence, Rossman illustrates the transformative power of adopting a digital-first approach and leveraging technology to scale solutions and optimize operations.

The keynote culminates with insights from “Big Bet Leadership,” where Rossman articulates the criticality of making and managing big bets to pivot an organization toward future growth opportunities. He discusses the strategic imperatives of such decisions, the risk management involved, and how to foster a culture that supports and champions bold moves. Audience members will leave with a clear understanding of how to meld leadership, culture, and innovation practices to participate in their industries and lead them boldly into the future.

Leaving Your Audience with:

  • Understand Amazon’s Leadership Principles: Learn from Amazon’s core leadership principles to enhance decision-making and cultivate a high-performing team culture.
  • Cultivate a Culture of Innovation: Adopt strategies to embed a continuous innovation cycle within your organization, driving efficiency and competitiveness.
  • Customer-First Mindset: Use a customer-centric approach to transform business processes, enabling scalability and improved customer satisfaction and loyalty.
  • Risk Management in Bold Decisions: Understand how to strategically manage and mitigate risks when making and implementing big bets.
  • Championing Bold Leadership: Develop a leadership style that encourages bold thinking and decisive action to navigate and lead through industry disruptions

Lessons from the Launch of the Amazon Marketplace Business — How You Become a Big Bet Legend in Your Industry

In 2002, Amazon was being referred to as “Amazon.org”, “Amazon.org” and “Amazon.toast”. The stock hit a low of five dollars. Ninety percent of Amazon’s business was books, CD music sales and VHS video unit  sales. But Jeff Bezos had an ambitious vision to become “the everything store”. He just needed the right model and team. Amazon hired John Rossman to play a key role in leading and scaling the Amazon marketplace, which accounts for 60% of all units sold at Amazon today.

This keynote is the story of creating the Amazon Marketplace business and what business leaders can learn and apply to their businesses today.

Combining The Amazon Way, Think Like Amazon, and Big Bet Leadership, Rossman will take your audience through an entertaining and provocative discussion that will impact the way you think, the way you lead, and the culture of your organization.

If you are undergoing a transformation, repositioning, or growth strategy, you can’t afford not to study and learn from the business that changed retail, logistics, and so many other industries—from the Amazon leader who captured the story, John Rossman.

This keynote starts with an entertaining video framing the situation and challenging circumstances that Amazon faced in 2002. It then delivers the proven leadership principles and tactics to deliver transformational change in your organization.

Learn about true customer obsession, how to spot friction, why “metrics” need to be a verb, the secret to Amazon’s innovation process, how to deliver results despite setbacks, and much more.

Leaving Your Audience with:

  • Visionary Leadership Insight: Learn how Amazon transformed from a struggling bookseller to “the everything store” and the most interesting company of the digital era.
  • Scaling Innovation: Discover strategies for scaling the Amazon Marketplace.
  • Change Frameworks: Apply frameworks from “The Amazon Way,” “Think Like Amazon,” and “Big Bet Leadership” to lead organizational transformations.
  • Durable Leadership Principles: Understand the resilient leadership principles and tactics that navigated Amazon through its early challenges to industry dominance.
  • Cultural Impact: Explore how Amazon’s culture of customer centricity, innovation and accountability can be replicated to drive success in your own organization.

Think Like Amazon — What’s the Future of Your Industry and Ecosystem?

This presentation is tailored to business leaders and investors interested in forecasting and creating the future of their industry.

Drawing from his extensive experience at Amazon, the Bill and Melinda Gates Foundation, T-Mobile, and dozens of client strategy engagements, Rossman explores critical components and mega-forces leading to change. Attendees gain exclusive insights into applying these methodologies to their strategies, accelerating growth and enhancing competitiveness in an increasingly competitive and dynamic marketplace.

Rossman’s discussion extends beyond replicating tactics; he encourages a paradigm shift in thinking. Attendees will explore the ‘thinking in outcomes’ approach, outlining practical steps for conducting scenario planning. This keynote segment is designed to provoke thought, spur innovation, and drive home the importance of a customer-centric approach coupled with robust thought experiments. 

Concluding with a forward-looking perspective, Rossman guides the audience through scenario-planning exercises to predict and react to future industry trends and challenges. This proactive approach prepares leaders to navigate their businesses through potential disruptions and equips them to play a pivotal role in shaping their respective ecosystems. Participants will leave with a clear set of principles and techniques that, when implemented, can transform their organizations into agile, forward-thinking competitors ready to thrive in the future digital landscape.

Leaving Your Audience with:

  • Adopt Amazon’s Strategic Mindset: Embrace continuous innovation and customer obsession to redefine industry standards and enhance business growth.
  • Practical Innovation Strategies: Understand how to “think in bets” by solving wicked problems.
  • Future-Proof Your Business: Utilize scenario planning to anticipate and effectively respond to dynamic market changes.
  • Cultural Transformation: Foster a culture that supports customer centricity, agility, resilience, and constant learning to thrive in the digital era.

Championship Habits — Team Culture and Tactics for High-Performing Teams

Inspired by his professional and family journey, John Rossman introduces the pivotal concept of “Championship Habits.” This keynote delves into the critical practices that distinguish top-performing teams from the rest. Rossman explores how these habits can be systematically cultivated to enhance team performance and drive substantial organizational success.

Cultivating a Culture of Excellence and Customer-Centricity

Rossman argues that the foundation of any high-performing team is a robust and dynamic culture that prioritizes excellence, continuous improvement, and customer obsession. He discusses the importance of creating clarity and alignment around shared goals, the benefits of a proactive and engaged leadership style, and the critical role of feedback and communication in fostering a culture of accountability and transparency. The keynote outlines practical strategies for leaders to embed these values deeply within their teams, ensuring that each member is empowered and aligned with the team’s objectives.

Tactical Execution of Championship Habits

Moving from culture to application, Rossman provides a deep dive into the specific tactics that embody Championship Habits. These include establishing rigorous standards for performance, using metrics to gain operational excellence and insights, and maintaining high-velocity decision-making. Through real-world examples and case studies from his time at Amazon and other leading companies, Rossman illustrates how these practices are implemented in day-to-day operations and how they contribute to teams’ agility and effectiveness.

This keynote promises to redefine what it means to build and lead high-performing teams and provide participants with a practical and proven framework for implementing a dynamic and sustainable winning game plan. Attendees will be equipped with the tools to transform their team’s culture, execute championship-level tactics, and develop an adaptable approach that consistently delivers superior results.

Leaving Your Audience with

  • Empowered Team Dynamics: Strategies to cultivate a culture of excellence and accountability that empowers teams to achieve their highest potential.
  • Practical Execution Tactics: Actionable methods for applying Championship Habits to day-to-day team operations and decision-making processes.
  • Sustainable Performance Frameworks: Insights on building resilient systems that maintain high performance through changing markets and challenges.
  • Winning Game Plan Methodology: A comprehensive blueprint for creating and sustaining dynamic teams that execute and innovate under any conditions.

Reinventing Healthcare & Insurance Through Customer Centricity, Innovation & Leadership — The Amazon Way

Rossman offers a roadmap for revolutionizing these critical sectors through relentless customer centricity, robust innovation, and transformational leadership.

Rossman unpacks the essence of Amazon’s customer-centric approach, illustrating how this relentless focus can be adapted to the healthcare and insurance fields to significantly improve service delivery, patient and client satisfaction, and operational efficiency. He highlights case studies and strategies from “The Amazon Way”, showing how these can be directly applied to enhance interactions at every customer touchpoint, streamline processes, and reduce inefficiencies, all while maintaining privacy and compliance with industry standards.

Expanding on the themes from “Think Like Amazon,” Rossman dives into the ’50 1/2 ideas’ that are particularly relevant to digital transformation in healthcare and insurance. He explains how embracing a digital-first mindset and integrating cutting-edge technologies like AI and big data analytics can lead to innovative solutions that are cost-effective, highly scalable, and precisely tailored to user needs. Rossman challenges industry leaders to think differently about legacy systems and entrenched practices, promoting a culture of innovation.

The keynote culminates with strategic insights from “Big Bet Leadership,” where Rossman elucidates the importance of making calculated, bold moves to lead disruptive change effectively. He discusses how the principles of leadership that guided Amazon through its most critical bets can be employed to spearhead reform in healthcare and insurance. Audience members will leave equipped with a blueprint for embedding customer centricity at the heart of their operations, leveraging innovation to solve complex challenges, and leading change that anticipates the future of their industry.

Leaving Your Audience with

  • A Customer First Framework: Learn how to apply Amazon’s customer-centric methods to enhance patient and client satisfaction in healthcare and insurance.
  • Innovative Problem Solving: Integrate cutting-edge technologies and innovative practices to address complex challenges within the healthcare and insurance sectors.
  • Leadership in Disruption: Adopt bold leadership principles from “Big Bet Leadership” to effectively navigate and lead disruptive changes.
  • Strategic Digital Transformation: Utilize the ’50 1/2 ideas’ from “Think Like Amazon” to drive digital transformation that scales and adapts to evolving market needs.
  • Operational Excellence: Implement Amazon’s strategies to improve efficiency, reduce costs, and deliver superior service quality.

“The audience LOVED your presentation and they took away many key learnings that they hope can be applied moving forward.”



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John Rossman | Leadership Keynote Speaker & Author