Operator-Led
Technical Diligence
Buy-Side Diligence · Sell-Side Representation · Post-Close Execution
The operator deal teams call when the stakes are too high for Crosslake or West Monroe. I represent private equity in software transactions—buy-side and sell-side—where technical risk, platform debt, or hidden COGS can derail value. I lead technical diligence end-to-end, serve as the technical counterparty to buy-side diligence teams, and where required, execute the first 90 days post-close to ensure the investment thesis survives contact with reality. To date, every diligence client has elected to retain me post-close—even when I advised that no remediation was required.
What I Do
Buy-Side Technical Diligence
- Lead technical diligence for software and tech-enabled acquisitions
- Identify platform risk, cost leakage, and scalability constraints
- Translate findings into underwriting-grade inputs and remediation plans
Sell-Side Technical Representation
- Pre-sale technical assessment mirroring a buyer's diligence lens
- Data room documentation that frames technical debt in investment language
- Technical representation during diligence calls—reduce retrade risk and diligence drag
Post-Close Execution
- Principal-led remediation where risk or value creation is material
- Aggressive cloud cost reduction
- Security and authentication rewrites
- Infrastructure modernization
AI & Modernization
I deploy AI where it creates durable product and operational advantage—not as a standalone initiative. This includes tuning open-source models on client-owned infrastructure and embedding them directly into production applications: onboarding automation, document ingestion, recommendation engines, agentic workflows. I establish foundational AI capabilities that teams continue building independently after my engagement, consistently compressing multi-quarter modernization efforts into materially shorter timelines.
Selected Outcomes
Delivered within 30 days post-close
- Built an AI-native document ingestion engine that compresses what was previously 45 days of manual processing into one business day—automating classification and extraction across 100K+ legacy documents
- Reduced CloudFront costs by 60% and compute by 40%, directly expanding EBITDA
- Built modern Firebase authentication powering a Flutter-based mobile app for 2.5M users
- Deployed enterprise-grade web application firewalls across portfolio companies—closing security gaps that had persisted since inception, delivered in weeks
- Delivered cloud-native, self-service SSL white-labeling capability inside a legacy codebase
- Complete network re-architecture and production deployment after years of internal stagnation
- Zero-downtime region migration from us-west-1 to us-east-1
- Business continuity planning plus implementation of cross-account, multi-region disaster recovery
- Identified and resolved a recursive request loop outside the scope of a post-close engagement, cutting web traffic by over 50% and eliminating corresponding downstream costs including observability and logging
How I Operate
Three Principles
Hands-on-keyboard expertise across modern tech stacks and cloud platforms. I assess core IP, architecture, scalability, and team capability with engineering precision—delivering investment clarity where traditional advisors see only complexity.
I identify critical risks and quantify value-creation levers with enough precision for underwriting—without pretending to scope full remediation before gaining access and authority. Clear enough to price, honest about what remains unknown until Day One.
One operator, end-to-end. The principal who runs diligence runs remediation—never brokered to juniors or a separate delivery team. No handoffs, no knowledge loss.
Background
Direct Access
Capacity is capped at three concurrent mandates to preserve principal-led execution.
For new mandates: include target ARR, deal stage (LOI / exclusivity / signed), and anticipated close date.
Latest Insights
Writing on PE, Technology & Value Creation