AI Strategy Consulting: Workshop & Advisory
We help leadership teams stop guessing about AI and start building it with their own team. This is our Workshop & Advisory track: a diagnostic, a prioritized roadmap, and a scoped pilot. Fixed-scope, no fluff.
This is Track B. WiscAI offers two parallel engagement tracks. Track B - Workshop & Advisory (this page) helps your team adopt AI on their own work. Track A - Discovery → Build delivers AI as a working system. They run in parallel, not sequence - pick what fits, or run both.
Strategy is only useful if it leads to action
Every engagement starts with understanding your business, not selling you a framework. Here's what we do together.
AI Opportunity Diagnostic
A focused working session with your leadership team. We map your workflows, surface AI opportunities, score them by impact and feasibility, and build shared alignment on where to start.
1 weekPrioritized Roadmap
A clear sequence of AI initiatives, from quick wins to longer-term transformation. Scoped to your resources and your risk tolerance. Written to be executed, not filed.
1-2 weeksPilot Design
We design the first AI pilot with clear success criteria, technical requirements, and a realistic timeline. You go into it knowing exactly what "good" looks like.
2-4 weeksExecutive Alignment
We help you build the internal case: board materials, leadership briefings, change management framing. AI projects fail more often on adoption than on technology.
Fixed-fee diagnostics. Fixed-scope engagements. No open-ended billing.
What this looks like in practice
Two Wisconsin engagements where strategy turned into shipped AI systems.
Commercial Printing AI Transformation
A Wisconsin commercial printer came to us with a workforce problem: long-tenured staff approaching retirement, with decades of operational knowledge held in people's heads and no documentation behind it. We ran an AI diagnostic session, mapped the workflows at risk, and designed four concurrent AI projects: invoice generation automation, AP invoice OCR, smart accounting workflow, and print operations intelligence. All four projects are now underway.
Personal Lines Insurance Meeting Prep AI
A top-tier captive personal lines insurance agent in Wisconsin needed to compress 1.5 hours of per-prospect data gathering into minutes. We scoped the workflow, mapped the data sources, and built an AI meeting prep platform: document extraction turning policy declaration pages into structured coverage analysis, gap identification, and recommendation tiers across home, auto, umbrella, and life. Multi-state coverage engine, multi-seat team support. Live in production.
See how strategy engagements land in your industry
Each pillar page breaks down the two-lane opportunity map - internal/operational versus customer-facing or regulated - with real examples.
- Featured by Apple in Best New Apps & Updates (LilSense)
- Serving collegiate and professional programs, including an NCAA national championship team
- Founded Wisconsin's longest-running AI practitioner community (meeting weekly since 2024)
- Co-hosts the AI Leadership Breakfast Forum with Steve Cretney (EVP, Colony Brands)
Common questions
Is this WiscAI's Track B - Workshop & Advisory engagement?
Yes. This page describes Track B - Workshop & Advisory, WiscAI's team-enablement engagement: a 1-week diagnostic, a 2-4 week pilot working alongside the client team, and an optional monthly advisory retainer. Track A - Discovery → Build - is described at /how-we-work and is for organizations that want AI delivered as a working system instead of an enabled team. The two tracks run in parallel, not sequence; clients can engage either alone or both.
What does AI strategy consulting from WiscAI include?
AI strategy consulting from WiscAI typically includes: opportunity discovery across internal and customer-facing workflows, prioritization using a structured scoring framework (staff-time impact, data readiness, feasibility, risk and compliance, change load, measurability), a roadmap with sequenced initiatives, and a clear recommendation on what to build first.
How long is a typical AI strategy engagement?
WiscAI's flagship discovery engagement is three weeks, fixed scope and fixed fee. Longer strategic advisory relationships are available for organizations that want ongoing executive-level AI counsel after discovery.
Who is AI strategy consulting for?
It's for leadership teams - CEOs, COOs, CIOs, VPs of operations, and boards - who need to make defensible decisions about where AI fits in their organization, not just technologists experimenting with tools.
Does WiscAI only advise, or does it also build?
WiscAI does both. The same team that advises on strategy also ships production AI systems - which is why the advice is grounded in what's actually buildable, not slides. Clients can engage for strategy only, build only, or both sequentially.
Ready to find your AI leverage points?
Start with a 30-minute conversation. We'll tell you honestly whether we're the right fit.
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