I built CAPTAIN from nearly 40 years of seeing how enterprise deals are really won.
Big Picture Selling became Coalition Selling™. Coalition Selling became software.
Philosophy, methodology, software. One way of thinking, carried all the way to the deal.
Looking back over nearly 40 years in this industry, I realize that every major role was teaching me the same lesson from a different angle. Computer science taught me systems thinking. Product management taught me how products solve business problems. Business development taught me ecosystems. Enterprise sales taught me how organizations buy. Strategic partnerships taught me that companies rarely win complex deals alone. These were never separate disciplines. They were different views of the same enterprise system.
Out of those experiences came a belief I call Big Picture Selling: enterprise opportunities do not exist in isolation. Every significant deal lives inside a larger business system of customer objectives, executive priorities, partners, funding paths, technical dependencies, and competitive pressures. Great enterprise sellers naturally think this way. Big Picture Selling simply gives that way of thinking a name.
A philosophy is not enough on its own, so it became a methodology. Coalition Selling is the governed methodology for identifying, understanding, and activating the coalition surrounding an enterprise opportunity: the people, partners, relationships, and outside influences that shape whether an opportunity moves forward.
And a methodology is only as good as a seller’s ability to apply it on a Tuesday afternoon with a live deal on the line. So the methodology became software. CAPTAIN is the enterprise reasoning platform for Coalition Selling. It operationalizes Big Picture Selling and Coalition Selling by helping enterprise sellers uncover the invisible coalition behind every opportunity and recommending the next best action.
That thinking was built across nearly four decades in enterprise technology, including Workday, Salesforce, and Oracle. Along the way I launched co-sell programs with AWS and Google Cloud, built strategic alliances with PwC, KPMG, and Deloitte, and turned partnerships into engines of revenue growth.
CAPTAIN is not an AI story. The AI is an implementation technology. What CAPTAIN applies is governed enterprise reasoning: recommendations that are evidence-labeled, confidence-bounded, and auditable, so a revenue leader can see what each recommendation rests on and what remains unknown. CAPTAIN recommends, and the seller stays in control of every decision.
Colleagues and partners, in their own words.
“I’ve had the pleasure of working with Jody across dozens of sales campaigns, and his strategic approach consistently stands out. He has a keen ability to quickly identify opportunities and is agile in adjusting strategies based on real-time results. As a Systems Integrator, I’ve found his insights and adaptability invaluable to driving success. I look forward to continuing our collaboration on future initiatives.”
“Jody, you are the example of Workday's culture for sharing and caring. Your creativity is great. There is so much we are all doing across industries, and regions that sharing is key to ensure we leverage each other's best practices, and know what doesn't seem to be producing results! Thank you for being an open book to both proactively sharing and always being there reacting to answer questions. Thanks for being a great Workmate!.”
“Jody’s contributions to Workday were plenty, from helping us source/convert pipeline through the partner ecosystem, to establishing new strategic large scale partnerships with leading organisations. Jody cuts across complexity and noise and focuses on what must be accomplished. A true professional with an excellent track record of results.”
“Jody is one of the few individuals who can rapidly assess business or technical situations and think strategically about how all the pieces of the puzzle fit together. I had the good fortune of working with Jody early in my career where we partnered to win, service and maintain business at a fast paced start up. He was the consummate team player - humble, knowledgeable, patient and always willing to go the extra mile. We reconnected recently as my organization navigates the Workday partner ecosystem and as always, his ability to understand the strategic nature of the potential relationship is extremely impressive. Any organization - large or small - would be luck to have Jody among its senior executives.”
“I have worked with Jody Schiavo for many years at Oracle and I have not met a more creative or genuine person. Jody excels in building and executing cloud adoption and awareness programs across both broad sales organizations internally and Oracle’s external partner community. Jody is a leader who thinks outside the box and isn’t afraid to go after something in a new and fresh way. He is a constant innovator who brings a combination of intellect, creativity, and compassion to every engagement.”
See how CAPTAIN reasons across a complex enterprise opportunity.
Looking back over nearly 40 years in this industry, I realize that every major role was teaching me the same lesson from a different angle. Computer science taught me systems thinking. Product management taught me how products solve business problems. Business development taught me ecosystems. Enterprise sales taught me how organizations buy. Strategic partnerships taught me that companies rarely win complex deals alone. These were never separate disciplines. They were different views of the same enterprise system.
Out of those experiences came a belief I call Big Picture Selling: enterprise opportunities do not exist in isolation. Every significant deal lives inside a larger business system of customer objectives, executive priorities, partners, funding paths, technical dependencies, and competitive pressures. Great enterprise sellers naturally think this way. Big Picture Selling simply gives that way of thinking a name.
A philosophy is not enough on its own, so it became a methodology. Coalition Selling is the governed methodology for identifying, understanding, and activating the coalition surrounding an enterprise opportunity: the people, partners, relationships, and outside influences that shape whether an opportunity moves forward.
And a methodology is only as good as a seller’s ability to apply it on a Tuesday afternoon with a live deal on the line. So the methodology became software. CAPTAIN is the enterprise reasoning platform for Coalition Selling. It operationalizes Big Picture Selling and Coalition Selling by helping enterprise sellers uncover the invisible coalition behind every opportunity and recommending the next best action.
That thinking was built across nearly four decades in enterprise technology, including Workday, Salesforce, and Oracle. Along the way I launched co-sell programs with AWS and Google Cloud, built strategic alliances with PwC, KPMG, and Deloitte, and turned partnerships into engines of revenue growth.
CAPTAIN is not an AI story. The AI is an implementation technology. What CAPTAIN applies is governed enterprise reasoning: recommendations that are evidence-labeled, confidence-bounded, and auditable, so a revenue leader can see what each recommendation rests on and what remains unknown. CAPTAIN recommends, and the seller stays in control of every decision.
What People Are Saying
“I’ve had the pleasure of working with Jody across dozens of sales campaigns, and his strategic approach consistently stands out. He has a keen ability to quickly identify opportunities and is agile in adjusting strategies based on real-time results. As a Systems Integrator, I’ve found his insights and adaptability invaluable to driving success. I look forward to continuing our collaboration on future initiatives.”
— Head of Sales, Workday Professional Services Partner
“Jody, you are the example of Workday's culture for sharing and caring. Your creativity is great. There is so much we are all doing across industries, and regions that sharing is key to ensure we leverage each other's best practices, and know what doesn't seem to be producing results! Thank you for being an open book to both proactively sharing and always being there reacting to answer questions. Thanks for being a great Workmate!.”
— Executive at Workday
“Jody’s contributions to Workday were plenty, from helping us source/convert pipeline through the partner ecosystem, to establishing new strategic large scale partnerships with leading organisations. Jody cuts across complexity and noise and focuses on what must be accomplished. A true professional with an excellent track record of results.”
— Executive at Workday
“Jody is one of the few individuals who can rapidly assess business or technical situations and think strategically about how all the pieces of the puzzle fit together. I had the good fortune of working with Jody early in my career where we partnered to win, service and maintain business at a fast paced start up. He was the consummate team player - humble, knowledgeable, patient and always willing to go the extra mile. We reconnected recently as my organization navigates the Workday partner ecosystem and as always, his ability to understand the strategic nature of the potential relationship is extremely impressive. Any organization - large or small - would be luck to have Jody among its senior executives.”
— CEO and Founder
“I have worked with Jody Schiavo for many years at Oracle and I have not met a more creative or genuine person. Jody excels in building and executing cloud adoption and awareness programs across both broad sales organizations internally and Oracle’s external partner community. Jody is a leader who thinks outside the box and isn’t afraid to go after something in a new and fresh way. He is a constant innovator who brings a combination of intellect, creativity, and compassion to every engagement.”
— Oracle Peer