Leo Hart

Chief Technology Officer at Showpad

Canton, Massachusetts, United States

About Leo Hart

Leo Hart is Chief Technology Officer at Showpad. Location: Canton, Massachusetts, United States.

CTO and engineering executive with 25+ years leading large-scale software organizations through modernization, turnaround, and growth. Proven track record of transforming delivery economics, scaling high-performing teams (200+ engineers), and leveraging AI, DevOps, and cloud platforms to accelerate time-to-market while materially improving reliability. Highlights: ● P&L responsibility of up to $30 million, annually. Executive leadership across $150 million organizations ● 25+ years software delivery and support experience ● 20+ years in Agile/DevOps transformation Specialities: ● Engineering org transformation & scaling (startup –> enterprise) ● AI-enabled development, DevOps, cloud and microservices ● Startup, turnaround, M&A and change leadership ● Scaled Agile delivery (Scrum, XP, Kanban, SAFe, LeSS) ● Hands-on software architecture, design and development (DDD, CQRS) ● Financial services, healthcare & software product background

Skills

  • Machine Learning
  • Artificial Intelligence (AI)
  • Network Security

Additional experience

  • Chief Technology Officer

    IntelyCare

    November 2022 – March 2026

Education

  • BS, Saint Michael's College
  • Braintree High School