Tom Hewitt

People-First Engineering Leader | Building High-Performing Teams | Advocate for Culture and Trust

Montverde, Florida, United States

About

Seasoned Software Engineering leader with 25+ years of experience building and scaling high- performance SaaS platforms. Proven success coaching and empowering cross-functional Agile teams, delivering secure and scalable cloud applications, and continuously improving engineering outcomes. Deep expertise in aligning product and engineering goals, modernizing architecture, and fostering a culture of quality, ownership, and customer-centric thinking. Skilled in software development, Agile frameworks, CI/CD, DevOps automation, cloud infrastructure, and outcome-driven leadership.

Experience

  • VP of Engineering at HomeSource Systems
    Jul 2025 - Present · 1 yr

  • iPipeline (14 yrs)
    • AVP - R&D
      Jun 2020 - Jul 2025 · 5 yrs 2 mos

      Head of Life Insurance Value Streams. Served as VP of Development and strategic leadership for multiple product lines. Head of R&D for the Evolve Platform service Successfully oversaw over 150 feature releases within 2 years by applying rapid release and deployment techniques, including zero-downtime deploy methods and low-impact rollback planning. Champion and evangelist for Agile methodologies.

    • Senior Director - R&D
      Jan 2020 - Jun 2020 · 6 mos

      Head of Development for company’s annuity order entry system, “Affirm”. Ensured planning and development of annuity withdrawals, exchange order processing and book of business pre-population functionalities in line with defined time and budget constraints. Enhanced functionality and performance specification by implementing next-generation API-first access points Delivered better response time up to 80% by executing performance improvement for SaaS API system.

    • Director R&D
      Jan 2018 - Jan 2020 · 2 yrs 1 mo

      Oversaw system rewrite of term insurance quoting system while maintaining commitment of time and budget. Provided exceptional support and implementation with ownership of feature-flagging tool, “LaunchDarkly”. Transformed authentication system replacement infrastructure from RSA to Ping Identity.

  • Senior Developer at avelo
    Sep 2007 - Jul 2011 · 3 yrs 11 mos

    Member of development team on Mortgage Systems and Originations (MSO) platform. Expert in mortgage system application processing and workflow. Worked onsite at our customer, Nationwide Building Society in the capacity of "Support Lead" for 18 months.

  • Analyst / Programmer at Chelsea Building Society
    Aug 1996 - Sep 2007 · 11 yrs 2 mos

    Member of Core System development team, responsible for development and maintenance of business critical systems for a small banking company. Expert in regular, savings and mortgage account systems with full auditing and overnight system processing.