Strategic Advisor, ex-Technical Director
Executive Coach to Technology Leaders


After months of AI experimentation, executives are now asking tougher questions about the value being delivered. You sense that AI is speeding up what's possible for your products and your org, but faster doesn’t always mean ROI.
Executives want to know that you’re making the right decisions for AI to earn its keep in your company. It’s on you to decide where agent tooling is paying off and deserves continued investment—and where it doesn’t.
This is an executive-level intensive for CTOs/CPOs, Heads of and VPs of Engineering or Product, leaders setting AI direction and accountable for ROI across multiple delivery teams.
This four-hour workshop teaches you:
How to evaluate your AI investments as a portfolio of smaller bets rather than a monolithic spend
A technique that improves how you explain to your executives (and to your teams) where to continue to invest in AI
The ultimate money story for Engineering + Product + Design: How to translate measurable technical improvements into business impact language
This workshop is different because it provides tools to have the strategic discussions that build executive trust, not a “how to do math” financial analysis.
A four-hour deep dive into how you can ensure that your AI spend is worth the effort and resources
The practical executive definition of AI ROI, how it differs from traditional product ROI, and why a tidy number isn’t the end of the story
Why agentic AI is many small experiments in your organization rather than one big experiment, and why that’s helpful for accountable leaders
How to think like a strong business operator from a technology background–not just a technologist–using the Innovation Accounting framework
3 techniques to evaluate your AI investment portfolio: Think Like An Angel, 5 Finance questions, and the Thanos Snap
The Business Value Evolution Roadmap: connect the dots between the 3 types of data used in engineering organizations
Translate measurable technical improvements into business impact language
The ultimate money story that Engineering + Product + Design want to tell
People Want To Win: decision-making & communication technique to clarify which parts of the organization deserve continued investment in AI
The Plan and Prep technique to take advantage of executives’ attention and address the 3 underlying ROI questions with confidence
Solution swap: how to differentiate signal from noise in maintainability and burnout problems that could hurt productivity and drive up cost
How to lead a software organization that still has developers in 5 years
Why you need to continually refine the mental model of how executives think about Engineering
Recognize what “ROI” is shorthand for and the levers that drive impact. Leaders who fail to address the underlying *question-behind-the-question are at risk of being sidelined.
Apply a framework to rate how AI is used in your engineering organization and the full costs–money, time, energy, and lost opportunities. The higher the costs, the greater the expectations for value.
An engineering leader’s job is to build the business and set it up to win. Master the three elements of a compelling business narrative for your investment choices.
Unintended consequences are gradual and fuzzy, until you can’t ignore them. Learn from peers how to recognize early warning signs and address problems before they explode.

Former Technical Director | Strategic Advisor

Executive Coach to Technical Leaders
VPs of Engineering and CTOs who need an answer when an executive asks "what's the ROI of our AI adoption?"
Product leaders setting AI direction, making investment decisions, and accountable for customer outcomes across multiple delivery teams
This workshop is NOT for AI practitioners or champions who do not have budget responsibility
Live sessions
Learn directly from Allison Pollard & Paul Tevis in a real-time, interactive format.
Lifetime access
Go back to course content and recordings whenever you need to.
A Peer Community That Gets It
Senior engineering and product leaders from other companies facing the same challenges.
Dedicated Q&A with Allison and Paul
A separate Q&A session for top questions immediately after the session (also recorded).
Bonus content to go deeper and continue learning
Exclusive takeaway one-pagers, further reading, script bank, and more.
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Learn with your teammates
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Run a cohort for your org
A dedicated cohort with a custom schedule and curriculum, tailored to your team.
Book a private cohort$499
USD
12–4pm EST