Enterprise Strategy · Digital Transformation · AI

Sean-William
Goodale

VP-level strategy executive. Former McKinsey · VMware · Verizon. I build and lead strategy functions at the intersection of enterprise transformation and AI.

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Career Arc
VZ
Verizon
Senior Director, Corporate Strategy
VM
VMware
Director, Corporate Strategy
MK
McKinsey & Company
Engagement Manager, Management Consulting
About

Most strategy fails because it never survives contact with execution.

Sean-William Goodale

My career has been built in the gap between strategy and execution — where ambitious plans meet the reality of large organizations and complex technology.

I spent six years at McKinsey advising Fortune 500 executives on digital transformation and large-scale technology modernization. At VMware and Verizon, the work shifted from advising to owning outcomes — translating strategy into enterprise programs that change how companies operate.

Across these roles I’ve evaluated nine-figure growth opportunities, designed operating models for new enterprises, stood up companies through carveouts, and built the AI operating model frameworks organizations use to turn emerging capabilities into measurable business value.

“Strategy is the easy part. Aligning leadership, technology, and execution fast enough to matter — that’s where the real work happens.”

AI will not transform companies by itself. Leadership, incentives, and operating models determine whether technology becomes leverage or just another expensive experiment.

Areas of focus
Enterprise Strategy
Digital Transformation
AI Adoption
Growth & Commercial Strategy
How I operate
Calm under ambiguity
Bridge between business and technical
Execution-oriented from the start
Structured, not rigid
Career Positioning

VP and Head of Strategy roles at AI and enterprise technology companies. Selectively advising on AI strategy, digital transformation, and corporate strategy.

Get in touch →
Education
University of Chicago Booth
MBA · Strategic Management & Economics
Exchange: IIM Bangalore · Dean’s Honor List
Northeastern University
BS Business Administration · Minor: Computer Science
Case Studies

Selected work

01Where Capital Meets Conviction
Verizon
Digital Channel Investment Case
Financial ModelingROI Strategy
Built the quantified $50–75M investment thesis for digital channel upgrades — modeling NPV, ROI, and payback across conversion scenarios to secure executive approval.
$437M NPV
At base case conversion lift
Verizon
Fleet Operations Transformation
Cost ReductionData & BI
Led enterprise fleet transformation — benchmarking, KPI framework, and business case identifying significant OpEx savings and asset right-sizing.
20% OpEx
Savings identified; ~4.3K vehicles for divestiture
VMware
Enterprise Value Expansion Strategy
Corporate StrategyM&A
Developed the strategic framework to double VMware’s enterprise value — presented to leadership and Broadcom CEO Hock Tan ahead of acquisition.
2× EV
Target over 3–5 year horizon
02Intelligence as Infrastructure
Verizon
Customer Churn Reduction
AI / MLSales Strategy
Redesigned churn tooling from broad marketing flags to precision targeting for frontline Sales — enabling focus on the top 1–5% highest-risk accounts.
Top 1–5%
Highest-risk accounts targeted
VMware
Telemetry-Driven Customer Success
Data StrategyRecurring Revenue
Converted product telemetry data from 10K monitored enterprise customers into actionable sales insights — building a commercial expansion engine.
10,000+
Enterprise customers on data-driven model
McKinsey
Data & AI Commercialization Framework
AI / AnalyticsInnovation Pipeline
Designed a five-stage commercialization framework to evaluate and fund analytics and AI innovations at a $27B+ global pharma and lab technology company.
$50–100M
Revenue opportunity on first concept advanced
03Complexity as the Starting Point
McKinsey
National Hospital System Integration
M&A IntegrationHealthcare
Led IT integration analysis across the largest US healthcare network by revenue — 700 facilities, 142 hospitals — identifying $150M in technology synergies.
$150M
Technology & operational synergies
McKinsey
$3B Energy Infrastructure Carve-Out
Carve-OutOps Stand-Up
Developed the strategic blueprint for NRG → GenOn divestiture — 46 power plants across 12 states. Enabled full operational launch within 18 months.
$3B
Transaction value · $50M outsourcing deal structured
McKinsey
Fortune 50 CIO Transformation Roadmap
IT ModernizationExecutive Enablement
Designed a 100-day onboarding and execution roadmap for an incoming CIO inheriting a $4.3B modernization initiative at a major aircraft manufacturer.
$4.3B
Technology portfolio prioritized & sequenced
Writing

Perspectives on
strategy & AI

01
AI Leadership
Mar 18, 2026
Conducting Your AI Symphony
On the difference between leading your AI symphony or passively joining the audience
Read →
02
AI Strategy
Mar 11, 2026
Building with AI feels a lot like the Film Memento
On the memory problem, the breadcrumb solution, and what it actually takes to compound your AI investment over time
Read →

Published on Substack — subscribe for future pieces

Contact

Let’s connect

Strategy, AI, and transformation — if that’s the work, let’s talk.

Actively exploring VP and Head of Strategy roles at AI and enterprise technology companies. Selectively available for consulting engagements in AI strategy, digital transformation, and corporate strategy.

Email [email protected]
LinkedIn linkedin.com/in/seanwg
Substack swgoodale.substack.com
Phone (857) 205-2047