Rick's leadership expertise focuses on effectively guiding organizations toward the successful realization of their objectives. From transformation strategy to delivery at scale, product operating models and agentic AI.
Dr. of Business Administration DBA · MBA · SA · A-CSM
Transformation · Delivery · Product · AI
Work with Rick
Short-term engagements, fractional leadership, and workshop intensives. Pittsburgh-based, remote-friendly.
Out now on Amazon®
More Clarity, Less Noise
by Rick Pollick
Two volumes — writings on mindset, people, process, product, data, and AI.
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Latest writing
How InvestmentThing works: a Claude strategist that proposes, a deterministic risk engine that overrules it, two brokers pretending to be one account, a second model that tunes the dials, and every expensive mistake I made getting there.
A practical walkthrough of building a systems atlas: the seven questions it has to answer, evidence based discovery instead of surveys, the schema that is the actual product, ownership as a social problem, decision records with a revisit condition, an interface where the relationships are the navigation, and the freshness protocol that keeps the whole thing alive after you stop looking at it.
Agentic AI is automating the base of the engineering pyramid, the junior work that teams were built on. That does not shrink your team evenly, it inverts it, pushing demand toward senior reviewers and architects while entry level roles collapse. Here is how to staff for the inversion without starving your own pipeline.
The context-engineering episode of Valuestream. Reliable AI agents fail on context, not prompts: what the model can actually see when it acts. The context budget, the four failure modes, and how to run context as a delivery discipline with version control, evals, ownership, and observability.
AI made writing code nearly free, but retiring it never got cheaper. That gap compounds into deprecation debt, a fast growing form of technical debt: dead paths, stale APIs, and un-migrated systems that quietly cap delivery throughput. Here is how to measure and govern it before it stalls your team.
Prompt engineering was never the real bottleneck. In production, agentic AI systems fail on context: what the model can actually see when it acts. Here is why context engineering is a delivery discipline, not a research problem, and how to run it with ownership, evals, and observability.
Apps
Built to make delivery, operations, and everyday life a little less boring.
Ezra
Design custom QR codes and get deep analytics — cheap.
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Football FantasyIQ
A full platform for fantasy-football insight — trends, projections, matchup intelligence, powered by the Sleeper API.
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AltaClario
Modern agile analytics for Jira & Azure DevOps — burndown, velocity, capacity, and release health in one workspace.
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Vantage
Gather every loyalty balance you have — value it all and turn it into trips.
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Overtone
Records all audio input and output with free transcription, summaries, and sharing — Mac and Windows today, iOS and Android coming.
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ShadoWatchr
Mac threat assessments and active defense in one place.
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Episode 5 — Live
Where value actually flows.
Episode 5: Context Is the Job. The context-engineering episode. Reliable AI agents fail on context, not prompts: what the model can actually see when it acts. A 2026 survey traced 57% of agent reliability failures to missing or inconsistent context, not the model. The context budget, the four failure modes, and how to run context like a delivery discipline. 22 minutes.
What people say
“Rick is dynamic, thoughtful, energetic, inventive, inspirational, articulate, consultative, and driven. He excels at breaking down complex challenges, driving transformation, and building team capability through innovative problem-solving.”
Mark Wuslich — Colleague - Product Manager & Scrum Master — UPMC Enterprises
Elsewhere
Select Technical Projects
Open-source code and experiments on GitHub.
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Linktree
Everywhere else to find Rick.
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Pittsburgh Technology Council
Regional tech community and programming.
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ProductTank Pittsburgh
Pittsburgh's product community — meetups, talks, and demos for PMs and product-minded folks.
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#PittAgile Meetup
Pittsburgh's local agile practitioner community.
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Portfolio Video
A short walkthrough of delivery leadership work.
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Get in touch
Advisory, fractional leadership, AI strategy, or just a coffee chat. Book a 30-minute slot, drop an email, or grab the resume.
