Richard Miles
Chief Technology Officer
Richard is a startup CTO, software engineer, and security researcher with over eight years of experience designing, building, and scaling high-performance systems across cloud, on-prem, and hybrid environments. As technical co-founder of Assessorly, he architected and implemented the platform end-to-end, translating complex valuation, tax, and spatial data problems into a scalable, audit-ready SaaS product.
Richard began his career building distributed systems and backend infrastructure, developing a strong foundation in system design, performance optimization, and security-first engineering. He specializes in turning early-stage ideas into production systems, with deep expertise in cloud architecture, spatial data modeling, CI/CD automation, and full-stack development.
His technical background includes optimizing PHP at the C level as a PHP-SRC contributor, building real-time systems capable of sustaining 100,000+ requests per second, and engineering mission-critical healthcare infrastructure at McKesson supporting over $120B in annual transaction volume, where reliability and security were non-negotiable.
An active security researcher, Richard has been recognized in DEF CON competitions and ranked Top-10 in McKesson’s internal web hacking challenge. He brings a security-first mindset to system design, informed by hands-on experience in threat modeling, exploitation, and defensive engineering.
Today, Richard continues to drive Assessorly’s technical vision at the intersection of data engineering, valuation analytics, and cloud-native system design.