Technology Assessment
Before a modernization program, a fundraise, or a major platform investment, you need to know what you actually have. A technology assessment answers that question directly — code, architecture, team, and data — before commitments are made.
The $20M modernization program that started with an assessment
At LERETA — the second-largest property tax processor in the United States, handling $18 billion in annual tax disbursement volume — the four-year modernization engagement started with an accurate picture of what existed. Not what the documentation said existed. What actually ran in production, what was coupled to what, and where the real risk was in moving any of it.
That initial assessment shaped a $20M program. Sequencing decisions that looked arbitrary from the outside were determined by technical dependencies discovered during assessment — systems that could not be migrated in the order the business wanted, because the order the business wanted would have taken down $18B in tax processing for major US mortgage servicers.
At First American Financial — the world's largest title insurer at the time of the engagement — the same assessment discipline applied to M&A targets. One independent technology review of a nine-figure acquisition target led the company to walk away. The actual technical state of the target did not match the deal thesis. That is what accurate technology assessment looks like when applied to real financial stakes.
The most important thing an assessment surfaces is not what teams know is broken — it is what they have stopped seeing because they have worked around it so long. Every platform has assumptions baked into it that no longer hold. Finding those assumptions before a major investment is the whole point.
Six dimensions of a technology assessment
Code & Architecture Review
A direct read of the codebase and architecture: quality signals, patterns in use, technical debt load, test coverage, and where the real fragility lives versus where documentation says it lives.
Scalability & Performance Analysis
Can the platform hold at 5× or 10× current load? Identifying bottlenecks, architectural ceilings, and the specific constraints that cap growth before they become production incidents.
Security Posture Evaluation
Dependency audit, access control review, authentication and authorization architecture, exposed surface area, and the security debt that accumulated while the team was shipping features.
Team & Process Assessment
Key-person risk, documentation quality, development process maturity, on-call practices, and whether the team that built it can maintain and evolve it at the pace the business requires.
Data Infrastructure Audit
Data model quality, pipeline reliability, schema hygiene, migration history, and whether the data architecture can support the analytics and AI use cases on the roadmap.
Technology Roadmap Gap Analysis
Comparing stated roadmap against actual technical feasibility. Identifying what is achievable on the current platform versus what requires architectural change before it can be delivered.
"Shawn Livermore's expertise in our industry and technology stack was incredibly effective, and I'm certain our projects would not have succeeded without his involvement."
What a technology assessment engagement looks like
A clear sequence from access to executive briefing — typically two to three weeks end-to-end. An assessment without an account of what actually exists is just documentation of what people believe. Reach out to discuss a technology assessment engagement.
Days 1–2
Scope & Access
Align on the purpose of the assessment — pre-modernization, pre-fundraise, acquisition diligence, or new CTO onboarding — and establish access to code repositories, infrastructure documentation, and team interview schedules.
Weeks 1–2
Technical Review
Direct review of the codebase, architecture documentation, infrastructure configuration, data models, and third-party dependencies. Team interviews to surface the gap between what documentation describes and what actually runs in production.
Concurrent
Analysis & Synthesis
Identifying patterns, risks, and dependencies that are not visible in any single layer. The assessment connects code quality to architectural scalability to team capability to data integrity — surfacing cross-cutting risks that only emerge when the layers are read together.
Output
Opportunity Matrix
A robust, comprehensive matrix of AI and modernization opportunities spanning all areas of the business — migration paths, automation candidates, and modernization priorities ranked by feasibility, value, and sequencing risk.
Deliverable
Findings Report
Written assessment covering current state, confirmed risks, prioritized remediation paths, and the specific technical constraints that should shape any roadmap or investment decision that follows. Written for both technical and executive audiences.
Final
Executive Briefing
Structured walkthrough of findings with the leadership team, connecting technical findings to business implications — what the assessment revealed in terms of the decisions that follow: whether to proceed, what to address first, and what the identified technical risk means in financial terms.
Know what you have before you commit
Technology assessment from an enterprise architect with direct experience at LERETA ($20M modernization), First American (nine-figure acquisition reviews), and Kelley Blue Book (11 enterprise applications).
