Your code passes. Or it doesn't.

I help SaaS founders fix what's under the hood before investors, acquirers, or their own growth exposes it.

  • 20+ years in regulated SaaS
  • Led platforms serving 1.5M+ users
  • Multiple successful exits
  • HIPAA, FERPA, COPPA experience

Technical debt doesn't kill companies. Surprises do.

Investors bring in technical reviewers. Acquirers run code audits. Enterprise buyers ask for SOC2 and architecture docs. If your platform isn't ready, you find out at the worst possible moment: when the deal is on the line.

I've seen $10M acquisitions nearly collapse over undocumented infrastructure. Series A rounds delayed six months because of security gaps nobody surfaced. Enterprise contracts lost to competitors who could answer the compliance questions.

And for earlier-stage founders, the surprise comes differently. You built something that works. Users are growing. Then you hit the wall where the prototype can't keep up, and every new feature makes the foundation more fragile. The jump from prototype to platform is where most technical debt is born, and where it's cheapest to fix.

The founders who avoid these situations aren't lucky. They're prepared.

How I Help

Fixed-scope engagements. Clear deliverables. No hourly billing.

Technical DD Assessment

For founders preparing for fundraising or enterprise sales.

  • Codebase and architecture review
  • Security and compliance gap analysis
  • Technical debt inventory with risk ratings
  • Executive summary for non-technical stakeholders
  • 90-minute walkthrough call

Timeframe: 10-15 business days

Acquisition Technical Prep

For founders entering due diligence with a buyer.

  • Full technical DD assessment
  • Documentation package for acquirer questions
  • Remediation roadmap with priorities
  • Technical interview prep
  • On-call support through DD

Timeframe: 4-8 weeks

From Prototype to Platform

For teams whose prototype works but won't scale.

  • Architecture and scalability assessment
  • Security and technical debt review
  • Remediation roadmap with effort estimates
  • Documentation of findings and recommendations
  • Walkthrough sessions to review findings

Timeframe: 1-4 weeks

Fractional CTO Retainer

For companies needing ongoing technical leadership.

  • Weekly strategy calls
  • Architecture and decision support
  • Team mentoring and code review
  • Hands-on coding when needed (Node, C#, JS/TS)
  • Board/investor communication

Timeframe: Monthly engagement

Beyond the Title - Life Coaching for Tech Leaders

Who are you outside of work? Find what you actually enjoy. Design the next chapter intentionally. Coaching from someone who's lived it.

Learn more about coaching

Who I Am

I started my career in the U.S. Air Force, including a deployment to the Middle East. When I got out, I went after a degree in physical therapy, but the insurance side of healthcare pushed me toward technology instead. I became a network admin, then a developer, then a senior developer. Nearly every tech role I've held has been in EdTech, eLearning, or coaching platforms in regulated industries.

One of my early career-defining roles was at HealthStream, where I was part of the team that rewrote their core platform. When I joined, their stock was trading under a dollar. Today they're a publicly traded healthcare SaaS company doing nearly $300 million in annual revenue.

In 2008, I joined SimplyDigi as an early technical leader with significant equity. I was core to the platform's growth from the ground up, scaling it to over 600,000 users before we sold to Vector Solutions. At Vector, I led the consolidation of six acquired platforms into a unified SaaS architecture serving over 1.5 million users. At eLuma, I cut defects by over 90% and reduced cloud costs by 80%.

I've been fully remote since 2008, splitting time between Tallahassee, FL and Costa Rica.

Every company I've worked with has been in regulated environments: K-12 EdTech, healthcare-adjacent systems, coaching platforms handling sensitive data. I know what it takes to build systems that survive compliance scrutiny.

Beyond technical work, I also coach tech leaders through life transitions. Sometimes the system that needs fixing isn't the code.

  • Led LMS platforms serving 1.5-2M users
  • Technical due diligence experience on both buy and sell side
  • Deep expertise in HIPAA, FERPA, and COPPA compliance

Let's Talk

Book a 30-minute call to discuss your situation. No pitch, no pressure. We'll figure out if I can help.

Prefer email? Reach me at info@henryirvin.com