Fractional CTO for Financial Services & Fintech Companies
Regulated financial technology has unique constraints: compliance requirements that shape architecture, data that cannot be lost, and audit trails that must be designed in from the start — not retrofitted. Experience across payroll, title insurance, utility billing, payments, and PE-backed fintech.
From payroll card systems to $5B title insurance infrastructure
At Ceridian — the payroll and HR technology company — I designed and built a debit-card-based financial management system for employees. That engagement required understanding the full technology stack of a payment product: card provisioning, transaction processing, balance management, and the regulatory environment that governs employee-facing financial products.
At NYSEG / Energy East — Fortune 500 #522, a New York State utility — I worked in a CIO-reporting capacity on financial systems for utility billing and operations. At First American Financial, then the world's largest title insurer, I served as Senior Enterprise Architect across a $5 billion conglomerate with 770 applications and a proprietary dataset covering 100 million US properties.
More recently, through the FNDRS PE platform, I have built AI-powered financial due diligence automation and RAG-based intelligence over financial documents — the technology layer that helps private equity firms move faster and with greater precision on acquisition decisions.
Six dimensions of financial services technology
Financial Platform Architecture
Designing the core technology platforms that power financial products — from payroll and HR systems to title insurance data infrastructure to credit union core banking integrations.
Payments & Cards Technology
End-to-end design and implementation of payment systems including debit card programs, transaction processing pipelines, and employee financial management platforms built to PCI compliance standards.
RegTech & Compliance Systems
Technology architecture for regulated financial environments — utility billing, title insurance, payroll, and credit union systems where compliance is not optional and audit trails are architecturally required.
AI for Financial Services
Fraud detection models, loan processing automation, AI-assisted financial document review, and RAG-based intelligence over large financial datasets. Practical AI applications where risk controls are part of the design.
Legacy Modernization
Utility billing systems, COBOL-era financial infrastructure, and proprietary platforms rebuilt for modern architectures — with the sequencing strategy that keeps core financial operations running throughout.
M&A Technical Diligence
Independent technology assessment for PE-backed fintech acquisitions. Evaluating platform architecture, data integrity, compliance posture, and integration complexity before the deal closes.
"Our industry of insurance is heavily regulated — Shawn Livermore understood that and delivered a powerful, secure, and compliant app."
The structural differences that make fintech architecture a specialty
Financial technology has compliance requirements that most software categories never face. PCI DSS for payments, state utility regulations for billing, RESPA and state licensing for title — these are not checkbox items. They determine how data flows, where it can reside, how long it must be retained, and who can access it.
PE-backed fintech companies face an additional set of pressures: a compressed timeline to demonstrate platform scalability, often a legacy architecture acquired through investment that was not designed for the growth expectations now attached to it, and investors who need to understand the technology risk in terms that connect to financial outcomes.
The AI opportunity in financial services is significant and practical: fraud detection that operates at transaction speed, loan processing automation that reduces manual review by 60–80%, document intelligence that extracts structured data from unstructured financial filings. The challenge is deploying these capabilities in environments with strict data governance requirements and zero tolerance for model errors that affect real financial outcomes.
A fractional CTO engagement in financial services means navigating all of this from direct experience — across payroll technology, title insurance, utility systems, and PE-backed fintech — rather than learning these constraints at your company's expense. For acquisition evaluation in financial services, see the M&A advisory practice. Reach out to discuss your platform.
Before the conversation — score your bank, insurer, or fintech for AI.
A 7-minute, 6-dimension AI readiness assessment built for financial services — model governance, fraud, compliance, AML/KYC, and legacy core realities baked in. Free, instant results.
Take the assessment →Fractional CTO for financial services and fintech
Direct experience across payroll technology, title insurance, utility financial systems, payments architecture, and PE-backed fintech AI — available as a fractional engagement.
