Head of Software Engineering

Boston, Massachusetts

Addison Group
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Location: On-site, 5 days/week Downtown Boston, MA Reporting into CTO


We are conducting a confidential search for a Head of Engineering to lead the next phase of growth for a cutting-edge technology company operating at the intersection of commercial and defense software. As we target $100M in ARR within the next three years, this leader will play a mission-critical role in:


  • Hiring, leading, and retaining top-tier engineering talent while consistently elevating team performance.
  • Driving the full lifecycle of a new class of predictive, dual-use software-from prototype to production-supporting both commercial and defense verticals.
  • Launching and scaling products across complex domains, from contested logistics to missile defense.

Key Outcomes (First 18-24 Months)

  • Scale the engineering team from 15 to 50+ (backend, frontend, ML, etc.), raising technical excellence and team cohesion.
  • Drive product velocity by transitioning 5-10 prototypes into full production across diverse and demanding environments.
  • Deliver enterprise-grade reliability (>99.5% uptime) and accelerate integration with external systems.
  • Oversee deployment into high-security environments (e.g., IL-5/IL-6), supporting compliance initiatives including CMMC and FedRAMP.
  • Represent U.S. Engineering in high-stakes customer engagements and serve as the technical voice in business development.

Ideal Candidate Competencies

  • Domain Understanding: Experience building and scaling platforms for defense or complex operational domains. Comfort working with tactical users and senior decision-makers.
  • Engineering Excellence: Proven track record of owning full-stack development across both greenfield (0 to 1) and scaling (1 to n) efforts. Strong background in cloud and edge deployments.
  • Leadership: Natural leader with a builder's mindset. Demonstrated ability to grow and mentor high-performing engineering teams.
  • Communication: Able to clearly articulate product and technical vision to a diverse set of stakeholders-from engineers to military leaders.

Date Posted: 28 April 2025
Job Expired - Click here to search for similar jobs