2–4 Week Strategic Engagement

TRAILS Strategy Sprint

From scattered AI interest to a board-defensible AI portfolio — in 30 days

A structured engagement that takes your organization from "we should do something with AI" to "1–3 validated bets with a 90-day roadmap, success metrics, and kill/scale criteria."

Starting at $15,000

The Challenge

Your organization knows AI is important. You may have run pilots, invested in tools, or seen your team get trained. But:

Multiple AI ideas in flight but no framework to prioritize them

Pilots that generated activity reports instead of business outcomes

Can't articulate to leadership why one AI bet is better than another

Competitors are shipping while you're still 'evaluating'

Every vendor says their tool is the answer — but the answer to what, exactly?

The gap between 'AI-curious' and 'AI-capable' keeps widening

Your team built prototypes but nobody knows which ones deserve real investment

Board or leadership wants a plan — and 'we're exploring' isn't cutting it anymore

How TRAILS Drives the Sprint

The Accelerants (Sprint focus)

Reveal

Find the AI opportunities tied to real business impact.

Act

Build the 90-day plan and launch the first bet.

The Stabilizers (Sprint foundation)

Trust

Establish guardrails early.

Learn

Build the Traffic Light Model from day one.

Sprint Structure

Week 1

Discover

— TRAILS Diagnostic

AI readiness assessment, current initiative audit, stakeholder interviews, opportunity landscape mapping

TRAILS Diagnostic Report — where you stand today

Week 2

Prioritize

— Use-Case Triage

Score opportunities against business impact, feasibility, risk, strategic fit. Pressure-test assumptions.

Use-Case Scorecard — ranked and validated

Week 3

Plan

— Roadmap Build

90-day plan with 1–3 defensible bets, success metrics, resource requirements, kill/scale criteria, executive narrative

90-Day AI Roadmap + Executive Briefing Deck

Week 4

Launch (optional)

— Initiative Kickoff

Launch the first bet with the team, set operating cadence, assign ownership, establish feedback loops

Running initiative with clear ownership and cadence

What You Get

TRAILS Diagnostic Report

A comprehensive assessment of your AI readiness across all six TRAILS dimensions.

Use-Case Scorecard

Every AI opportunity scored and ranked against business impact, technical feasibility, risk, and strategic alignment.

90-Day AI Roadmap

1–3 validated bets with success metrics, resource requirements, dependencies, and milestones.

Kill/Scale Criteria

Traffic Light Model built into every bet. Clear thresholds for double down, adjust, or stop.

Executive Briefing Deck

A board-ready narrative for internal sell-through.

Governance Baseline

Foundational guardrails for data, privacy, and tool usage.

Why This Isn't Another AI Strategy Deck

Decision Framework, Not Slide Deck

You're not buying a document — you're buying decision discipline.

Kill/Scale Discipline Built In

Every bet has a Traffic Light. No more zombie pilots.

Operator-Built

Flexible Blueprint

Designed to adapt as AI models, tools, and your market evolve.

Speed to Value

Direction in 2–4 weeks, not 2–4 months.

Investment

Sprint Lite

$8,000 – $12,000

Duration: 1 week

Best for: Teams that know their landscape but need focused triage + roadmap

Includes: Use-case scorecard, 90-day roadmap, executive briefing

Buyer approval: Single stakeholder

Strategy Sprint

$15,000 – $25,000

Duration: 2–3 weeks

Best for: Most organizations — full diagnostic, prioritization, and planning

Includes: Full TRAILS Diagnostic + everything in Lite

Buyer approval: Single stakeholder

Sprint + Launch

$25,000 – $30,000

Duration: 4 weeks

Best for: Organizations ready to launch the first bet before the Sprint ends

Includes: Everything in Sprint + Week 4 initiative kickoff and cadence setup

Buyer approval: Single stakeholder (light executive sign-off for $25K+)

The Math

Scenario	Investment	Outcome	Return
One validated bet ships	$15,000	Avoided $200K+ in failed pilot spend by killing 2 weak bets early	13x return (savings)
Two bets reach production	$25,000	$500K in operational efficiency gains within 12 months	20x return
Portfolio approach scales	$30,000	$1M+ in new revenue/savings from AI-powered workflows	33x+ return

Frequently Asked Questions

What Happens After the 90-Day Plan?

The next question is: how do you scale this across the enterprise?

TRAILS Operating System

Scale AI adoption across your business

Ready to Get Your Direction Locked?

Every Sprint starts with a free 30-minute strategy call.