Customer Experience, Service & Success

Big Bet Leadership AI Boosts High-Stakes Business Decision-Making

New AI-powered digital advisor accelerates digital transformation and value creation by integrating AI with proven business frameworks as published in Big Bet Leadership: Your Transformational Playbook for Winning in the Hyper-Digital Era by John Rossman
Big Bet

Business transformation advisory firm Rossman Partners has released a core AI-enabled business advisory tool and service with the launch of Big Bet Leadership GPT. The specialized AI advisor guides and expedites strategic analysis, communication and execution using the principles outlined in Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era, the 2024 book co-authored by John Rossman, early Amazon executive, keynote speaker and founder of Rossman Partners, and Kevin McCaffrey, a former T-Mobile and Google Strategy Leader.

Leveraging OpenAI technology, Big Bet Leadership GPT turbocharges the ability of business executives and entrepreneurs to make high-stakes business decisions with confidence and clarity. By creating a powerful analysis and creative agent combined with the book’s structured frameworks, innovation techniques and other reinvented strategies, it further accelerates the ability of business leaders to excel at a critical part of their job—creating competitive advantage and sustained business value through transformations.

To optimize use of Big Bet Leadership GPT, Rossman Partners has also made available for download engineered prompts, designed to speed and sharpen the ability to successfully put in place tactical elements from the book, including:

  • The What Sucks Memo—addressing critical pain points and challenges within an organization or project, candidly reporting what isn’t working, where the biggest risks lie and what obstacles might derail progress.
  • The Outcome Definition Memo—defining what success looks like for a Big Bet initiative, ensuring the entire team is aligned on the desired impact, key metrics of success and how the outcome supports broader strategic goals.
  • The Outcome Financial Memo—quantifying the financial implications and goals of a Big Bet initiative, it complements the Outcome Definition Memo by providing a financial lens through which the success of the project can be measured.

The prompts can be used in conjunction with additional resources, including a Big Bet Leadership Journal, a Big Bet Preflight Scorecard, Big Bet Leadership Workshops and more.

The resources and advisory services offered by Rossman Partners have helped a growing number of business leaders across numerous industries meet and exceed aggressive targets. Among them, Jim VanderGiessen, owner and president of equipment designer and manufacturer ProChiller, credits Rossman with helping spur the creation of their QUAD 22 Series of dairy chiller systems, which have a higher chilling capacity, are more energy efficient and are 25% cheaper to manufacture than leading market alternatives.

“John challenged me to think more critically, to create a differentiated value proposition and customer experience and tackle our cost structure,” said Mr. VanderGiessen. “His unique combination of know-how and business-ready tools add enormous value and have prepared me and my leadership team to tackle this important work ourselves in the future.”

He added, “There is no way a firm our size could have afforded to engage a traditional leading management consulting firm to do this work. John has found a way to bring the highest quality strategic expertise to the middle market.”

“In creating the universe of Big Bet Leadership tools, we asked ourselves the kinds of questions we typically ask our clients—how do we create a differentiated category of business transformation advisory services which dramatically improves the impact while being an order-of-magnitude more accessible than leading strategic advisors?” said Rossman. “Our answer was a unique playbook designed to guide senior executives to be systematic at high-stakes, high-risk strategies—what we call Big Bets—combined with an AI advisor and toolkit, and our experts available on a flexible basis. With this approach, we believe our value ratio is, at a minimum, 10X that of legacy management consulting.”

Rossman added, “Our focus on solving complex, meaningful problems, aligning our compensation with outcomes and our innovative delivery approaches combine for a true partnership, independent thinking and advice.”

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