Hi, I'm Shawn Livermore

I've spent nearly 3 decades helping companies make better technology decisions—from Fortune 500 enterprises to high-growth startups. Whether it's preventing costly mistakes, modernizing legacy systems, or implementing AI strategy, I bring clarity and execution to complex technical challenges.

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The journey

My path into technology started with curiosity and evolved through solving real problems. In the late 1990s and early 2000s, I worked with Fortune 500 companies like H&R Block, Kelley Blue Book, and First American Title—learning how large organizations think about technology, risk, and change in complex, high-stakes environments.

At First American Title, I was responsible for technology strategy across 900 software engineers and 770 applications. When we were evaluating a $100 million acquisition, my technical investigation revealed fundamental problems that led us to walk away from the deal. That experience taught me that my job isn't to tell people what they want to hear—it's to help them make better decisions.

In 2011, I founded an online marketplace that I grew from zero multiple millions in revenue. Raising venture funding, making payroll, and having real skin in the game fundamentally changed how I think about technology decisions. I returned to consulting with a different perspective—supporting Carvana through their $2B valuation and IPO, and leading enterprise modernization at LERETA, the 2nd largest payment processor of its kind in the United States, (5 year, $20M project).

I've learned that most technology problems are actually people, process, or communication problems in disguise. My job is to cut through the complexity, align stakeholders, and create clear paths forward—incorporating AI at all possible opportunities.

Looking forward, my focus has been on AI and how it intersects enterprise architecture for mid-sized organizations. I've been helping companies expand their teams, platforms, and infrastructure to properly and comprehensively leverage AI in this golden era we are now in.

Technology leadership journey across nearly 3 decades

Carrying the AI and technology vision for organizations who need a fractional CTO or fractional CAIO.

2024 - 2026

Now leveraging AI and nearly 3 decades of senior level technology leadership experience to help businesses as a fractional CTO and fractional CAIO.

Fractional
AI
CTO
CAIO

2020 - 2024

Sr. Enterprise Architect | LERETA

Led $20M modernization for 2nd largest US property tax processor ($18B annually). Managed 30+ developers across 2 flagship product rebuilds.

FinTech
Legacy Modernization

2017-2020

Principal Architect | Simpluris

Chief architect for class action settlement administration company. Full solution design, architecture, and team leadership.

FinTech
Legal
Architecture

2016-2017

Inventory Data Team Lead & Solutions Architect | Carvana

Architected vehicle inventory data systems processing for $2B valued company. Supported IPO process and partner integrations.

Pre-IPO
Team Lead

2011-2016

CEO & Founder | Ziptask

Built SaaS platform from $0 to $2M revenue. Raised 6 rounds of venture funding. Complete platform architecture and business development.

Startup Founder
Venture Capital

2009-2011

Chief Enterprise Architect | First American Title

Saved the client $120M through M&A technical due diligence. Led architecture for world's largest title insurance company with ~900 engineers and 770 applications.

Fortune 500
Fintech
Digital Transformation

2006-2009

Enterprise Architect | Oakwood Worldwide

Oversaw all IT architecture for 3,000-employee global organization. Integrated 80+ applications across multiple continents.

Global Enterprise
Fintech
Real Estate

2000-2006

Solutions Architect | Multiple Fortune 500s

Led technology implementations for H&R Block, Kelley Blue Book, WellPoint, CompUSA, PacifiCare, Blue Shield of CA, and many others. Built reputation as trusted enterprise architect.

Consulting

Impact by the numbers

Nearly 3 decades solving complex technology challenges at scale—from preventing costly mistakes to delivering multi-million dollar transformations.

Protected Value

$100M+

Advised on a 100m+ acquisition through technical due diligence at the #1 title insurance company in the United States

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Projects Delivered

$20M+

Multi-year enterprise modernization initiatives successfully executed at scale for mid to large organizations

Engineers Led

900+

Managed and influenced across Fortune 500 engineering departments organizations

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Philosophy

"I believe technology leadership is about making complex decisions with incomplete information, then having the conviction to follow through. It's about translating between boardrooms and engineering teams, between business objectives and technical constraints. Most importantly, it's about honesty—telling clients what they need to hear, not what they want to hear. My success is measured by your outcomes, not my billable time."

"I have worked with Shawn and I know his talent and leadership can have an enormous impact in a consulting engagement. I have seen it first-hand."

Pete Klein
Software Development Manager, Microsoft

Amazon top 10 best-selling technology author

Authored three books on .NET software development and interactive design. Authored a top-10 list business non-fiction book on succeeding in the tech industry.

Book cover for 'Average Joe' by Shawn Livermore, featuring a detailed illustration of a brain wearing black glasses on an orange background, with the subtitle 'Be the Silicon Valley Tech Genius' and a quote from Sean Ellis.
Amazon Top 10 Best-Seller

The Amazon top-10 best-selling book in 3 categories covers numerous tech entrepreneurial founders and software developers, and the exciting brands or products that they created.

Cover of the book Professional WPF Programming featuring a black and white photo of a man and the WPF acronym in large yellow text.

Professional WPF Programming

This book gives you the tools and code to master WPF—from creating rich graphics to improving performance, security, and enterprise design.

Cover of the book ASP.NET 2.0 instant results showing three men above the title with authors Imar Spaanjaars, Paul Wilton, and Shawn Livermore listed below.

ASP.NET Instant Results

ASP.NET 2.0 Instant Results lets you quickly build dynamic web pages with 12 ready-to-use projects and full source code.

Ready to transform your technology?

Whether you need strategic CTO guidance, AI implementation, or enterprise modernization—let's talk.

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