M & A Advisory
Starting with technology assessments to full due diligence and beyond—providing private equity groups with focused technology advisory engagements.
Unpack & crystalize acquisition targets
I've worked with private equity groups to gain clarity on product direction, technical architecture, and operational execution.
- Pre-acquisition technical due diligence — Evaluating codebases, architectures, and data models for scalability, maintainability, and modernization cost.
- Architecture-to-valuation translation — Converting technical health into financial impact, linking modernization and automation potential directly to EBITDA multiples.
- Post-acquisition integration planning — Creating enterprise diagrams and playbooks for merging acquired systems, data, and workflows into cohesive platforms.
- Modernization strategy for portfolio companies — Designing AI-first roadmaps that replace legacy systems with intelligent, cloud-native architectures.
100m+ dollars saved on acquisition due diligence
Proven impact across enterprise modernization, M&A, and technology leadership. From $100M savings to $20M+ transformations—see the outcomes.
M&A Due Diligence
Prevented a costly $100 million acquisition by leading deep technical due diligence for the world’s largest title insurance company.
The intellectual capacity and technical maturity of Shawn Livermore exceeded expectations.
Hands-on expertise, architecture, & leadership—for M&A.
Assessing and defining a clear roadmap that aligns tech decisions with business goals, along with the implications and potential of AI.
Evaluating the technical solution viability and quality across full stack : UI/UX, front-end, middle tiers, APIs, Databases, Caching, and more.
Prepare for investment or acquisition by ensuring architecture and code are audit-ready.
Help your developers work smarter, communicate better, and grow into mature teams.
Diagram, plan, and implement AI, automations, and solutions to accelerate and sustain growth.
Client success stories
Proven impact across enterprise modernization, M&A, and technology leadership. From $100M savings to $20M+ transformations—see the outcomes.
Enterprise modernization at scale
Led 30+ developers to rebuild flagship products for 2nd largest US property tax processor ($18B annually).
Holistic Software Architecture
Architected and led development teams for a legal automation software company, aquired for $50M.
Software Product Design for Title Ins Web App
Reimagined and redesigned multiple windows desktop apps into a new design of a single, unified, modern web app.
iOS Web App Design and Webservices
Front-end iOS design and back-end webservices architecture and development to support the new iOS app.
DevOps CI/CD Pipeline Implementation
Helped one of the fastest growing legal processing companies in the United States to automate its continuous integration / continuous deployment DevOps pipelines.
A practical and proven advisory model for fast-moving private equity deal flow.
My goal is to provide fractional technical leadership that fills the gap between founding team vision and scalable execution.
01
Assessment & Discovery
Understand target products/services, and technical challenges & opportunities.
02
Strategy & Roadmap
Align technical goals with market and funding milestones.
03
Architecture & Execution
Design, review, and guide implementation of scalable systems.
04
Team Development
Coach internal teams to operate with confidence and velocity.
05
Ongoing Advisory
Regular check-ins to guide strategic pivots and product evolution.
"Shawn was exceptionally helpful to our business. He understood our industry well and delivered on the promise of transformational results."
"Shawn's work touched numerous areas of the company. His intellectual capacity and technical maturity exceeded expectations."
"Shawn analyzed our systems, then designed, built, and scaled our flagship application from the ground up."
"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."
"Shawn is razor sharp and expert-level. Can't say enough good things about his work."
"I've worked with Shawn in multiple engagements over the last fifteen years. Shawn has a trusted network of diverse talent and always operates with integrity - highly recommended."
Frequently asked questions
What technical issues most commonly affect acquisition valuations?
The most impactful issues are undisclosed technical debt requiring immediate capital, architecture that cannot scale to the acquirer's use case, licensing or IP issues embedded in the codebase, and security vulnerabilities that create liability. Discovering these after close is expensive — identifying them before defines deal terms.
How quickly can a technical due diligence review be completed?
A standard assessment takes 2–4 weeks for a mid-market target. Accelerated timelines of one week are possible for focused reviews. The appropriate depth depends on deal size and what is at stake financially.
What does a technical due diligence report cover?
A review covers architecture assessment, codebase quality, infrastructure costs, team capability, security posture, and a risk register with estimated remediation costs. Findings are calibrated to inform deal terms — price adjustments, escrow provisions, or post-close remediation plans.
Can you assess AI capabilities as part of an acquisition review?
Yes. AI capability assessment covers the target's data assets, model inventory, governance maturity, integration architecture, and AI team depth. For acquirers evaluating AI-positioned companies, this has become a standard component of the diligence process.
How Strong Is This Acquisition’s Technology?
A buy-side scorecard for evaluating a target’s codebase, architecture, team, security, technical debt, and data before you sign.
Take the assessment →Related Reading
Technical Due Diligence
What a rigorous technology assessment covers, how findings translate into deal terms, and what buyers miss.
Technology Exit Preparation
The architecture, documentation, and risk remediation work that determines how a platform presents to buyers.
The Real Cost of Technical Debt
How to measure technical debt in business terms and build the case for paying it down systematically.