# Technical Due Diligence *by: [Scott Booher](https://www.linkedin.com/in/scottbooher/)* Scott has led or contributed to more than 20 technical due diligence engagements across healthcare, publishing, and consumer products — in both senior staff and consulting roles. Evaluation scope has ranged from platform IP valuation and IT strategic plan validation to compliance program assessment, leadership evaluation, and technology vendor review. ### What Makes This Different The most valuable technical due diligence isn't a compliance checklist — it's a strategic read of whether the technology can support what the business needs to do next. That requires judgment built over time, not just a framework. - **25+ years of senior IT and operational leadership** in growth-stage and enterprise healthcare organizations — with the pattern recognition that comes from having seen many of these situations before. - **A former healthcare CIO/CTO perspective.** Having purchased healthcare technology and led organizations through diligence from the other side, Scott brings immediate credibility and a buyer's-eye view to every engagement. - **Deep familiarity with modern healthcare platform architecture.** Today's digital health companies rely on complex orchestrations of external services, APIs, open-source components, and cloud infrastructure. Scott evaluates these environments not just for what they are today, but for what they'll cost to maintain, scale, and keep compliant — and whether the architectural choices are defensible or will require costly rework. - **A structured, efficient approach.** Each engagement begins with a templatized foundation that is quickly tailored to the specific target, client priorities, and transaction context — ensuring capital efficiency for the client and a respectful, low-disruption experience for the target organization. ### Illustrative Due Diligence Outline #### Factors Shaping the Work Plan - Scope of review (technology, operations, or both) - Technology depth of the business (technology-enabled vs. technology-centric) - Number of products and services to evaluate - Industry vertical, regulatory environment, and competitive landscape - Documentation available prior to site engagement - Management team review in scope? #### Design Goals - Complement client financial analysis and commercial review - Make efficient use of site time — split teams and focus areas where possible - Keep Key Considerations front-of-mind throughout: what does the client most need to know? - Maintain a collegial, low-disruption engagement style with the target - Hold an ownership mentality throughout the work #### Illustrative Deliverables - Executive Summary with key findings and recommendations - Site Agenda Findings and Key Considerations - Technology stack: appropriateness, scalability, and risk - IT budget: current investment levels and estimated future requirements - IT organization SWOT, leadership assessment, and resource needs - Platform's ability to support projected sales targets - High-level Competitive Analysis (from publicly available information) - Addenda: target company documentation, detailed meeting notes #### Product and Service Review - Product overview, evolution, and demo - Product strategy, sales goals, and metrics - Product SWOT: current gaps, limitations, and future plans - Principal competitors and differentiation - PDLC processes and release maturity - Customer-specific customizations and commitments - Pipeline and upcoming commitments - Strategic partners, external dependencies, and terms #### Operations Review - Operations overview, staffing, and key processes - Technology dependencies supporting operations - Recruitment, training, and retention practices - Client/customer service processes and technology dependencies - Scaling operations to support sales growth, including CapEx and OpEx requirements #### Technology Organization Review - Key leaders, accountabilities, and org structure - Budget detail, spend categories, and forward estimates - Shared infrastructure across products - Business and IT interaction and interdependencies - Governance processes - IT strategic plan maturity - Security, disaster recovery, and compliance posture #### Detailed Product Technology Review - Architectural history and key design decisions - Scalability, reliability, and performance posture - Roadmap and release schedule - Technology stack overview, rationale, and future strategy - SDLC maturity: requirements management, release schedule, quality processes - Technical debt: scope, anticipated write-offs, and planned remediation - Team structure, skill sets, and core vs. outsourced capabilities - External dependencies: partners, terms, SLAs, and historical performance - Platform's ability to support projected growth > [!tip] Contact Scott > > [email](mailto:[email protected]) > >[linkedin](https://www.linkedin.com/in/scottbooher/)