Director, Head of Software Engineering

Job Description:

HITT is seeking a Head of Software Engineering to build a modern, AI-native software engineering practice from the ground up. This is a senior leadership role for an engineering executive with a builder's mindset: someone who has seen firsthand how agentic, AI-enabled development is changing the way software gets made - and who knows how to turn that shift into a durable advantage for one of the nation's largest general contractors. They bring the vision, technical depth, and people leadership to define how software gets built at HITT as the firm scales.

Reporting to the Chief Information Officer, the Head of Software Engineering will establish HITT's agentic engineering practice from scratch - setting the technical vision, standing up lean, agile product teams, and creating the standards, workflows, and culture that let small teams of AI-fluent engineers deliver high-quality software at a pace traditional development organizations cannot match. This leader understands that tools are only half the story: lasting change comes from people, and they will be as invested in recruiting and developing talent as in technology itself.

The Head of Software Engineering is accountable for the structure and growth of the engineering organization, the delivery of applications and platforms that serve HITT's project teams and jobsites nationwide, and the development of a new generation of AI-enabled engineering talent - hiring builders who already work this way and training HITT's existing developers in new methods. The role partners closely with senior leaders across the firm and serves as a visible champion for the responsible, high-leverage use of AI in how HITT builds.

Responsibilities

Agentic Engineering Practice

• Design, launch, and lead HITT's agentic engineering practice from the ground up, defining the operating model, team structure, and software development lifecycle for AI-enabled delivery

• Establish standards, guardrails, and best practices for agentic development - including AI coding agents and assistants, prompt and context engineering, human-in-the-loop review, automated testing, and evaluation

• Select, implement, and evolve the AI development toolchain (coding agents, LLM platforms, orchestration frameworks, and integrations), reassessing regularly as the landscape advances

• Partner with the CIO on the enterprise technology, data, and AI roadmap, ensuring the engineering practice accelerates HITT's broader digital transformation

• Ensure the software the practice ships are reliable, fast, and usable in high-velocity, decentralized field environments with users of many backgrounds

Talent, Recruiting & Enablement

• Recruit and hire engineers and engineering leaders who thrive in lean, agile, AI-augmented teams, and position HITT as a destination for top AI-native engineering talent

• Design and deliver training and enablement programs that upskill HITT's existing developers in AI-enabled development methods: from hands-on workshops and pairing to internal playbooks and certification

• Build a deep talent bench and clear career paths within the engineering function to ensure succession for senior roles

• Foster a culture of experimentation - fail fast and pivot - while managing risk responsibly

Delivery & Engineering Excellence

• Bring structure, accountability, and delivery discipline to the software engineering function, balancing execution (≈60%) with innovation (≈40%)

• Implement lean, agile delivery practices built on small batches, rapid iteration, continuous integration and deployment, and measurable outcomes

• Engineer security, quality, and compliance into every product, in alignment with HITT's zero trust cybersecurity strategy and NIST-aligned frameworks

• Define engineering KPIs and provide ongoing transparency to the executive team on velocity, quality, adoption, and business value delivered

• Leverage external partners strategically while avoiding over-reliance on consultants, building enduring in-house engineering capability

Executive Leadership & Cross-Functional Influence

• Serve as a strategic advisor to executive and operational leaders on what modern, AI-enabled software development makes possible for the business

• Partner with operations, virtual design and construction (VDC), preconstruction, and corporate functions to identify high-value opportunities for custom software, automation, and agentic workflows

• Represent HITT's engineering practice externally, in recruiting, industry forums, and the broader technology community, to attract talent and partnerships

• Champion responsible AI use, model governance, and data stewardship across the software portfolio

Qualifications

• Bachelor's degree in Computer Science, Software Engineering, or a related field; advanced degree preferred

• 12+ years of progressive software engineering experience, including 5+ years leading engineering teams or organizations; experience building a team, practice, or product organization from scratch is strongly preferred

• Current, hands-on experience with AI-enabled and agentic software development, including AI coding agents and assistants (e.g., Claude Code, GitHub Copilot, Cursor), LLM APIs, agent frameworks and orchestration, retrieval-augmented generation, and evaluation practices

• Demonstrated success recruiting strong engineers and training existing developers in new tools, methods, and ways of working

• Proven track record leading lean, agile teams that ship, balancing innovation with operational discipline in a complex enterprise

• Deep grounding in modern software engineering practice: cloud-native architecture, APIs and integration, CI/CD, DevSecOps, and test automation

• Strong product sense and user empathy; experience delivering software for field-based or operational users (construction, engineering, manufacturing, logistics) is a plus

• Executive-level communication and presentation skills; able to build conviction with C-suite audiences and translate deep technical topics for business leaders

• Financial and vendor management acumen, with experience owning budgets and managing platform and tooling ecosystems

In accordance with Virginia Senate Bill 215 (SB 215), the base salary range for this position is:

$130,000.00 - $210,000.00

Compensation in other cities and states may vary. HITT Contracting offers a competitive total benefits and compensation package including performance-based bonuses, premium health care coverage including vision and dental, employer-matched 401(k), wellness reimbursement program, paid holidays and time-off, and other voluntary benefits and leave types. The determination of salary is based on the candidate's individual professional experience, qualifications, education, skills, and training.