VP of Software Engineering

About the Role

You will lead software engineering at Nooks and own the technical vision for everything we build. That covers three things: the software we deliver under government contract, the platform our site teams and internal functions run on, and the AI strategy that shapes both. AI is not a side initiative here. It is in the products that win us contracts, and Nooks intends to be an industry leader in how we leverage modern AI. You will report to the CEO, sit on the executive leadership team, and set direction rather than receive it. You will be building the function while running it. The team is small today, the operating model is yours to define, and the plan for how it scales is a deliverable rather than a given. Priorities will shift as contracts land and as the business grows into new sites and new lines. You will need to hold a durable technical direction while making short-term calls with incomplete information, and you will be expected to bring answers instead of waiting for them.

Key Responsibilities

Engineering Organization and Delivery

• Lead, develop, and scale a software engineering organization accountable for delivery, quality, security, reliability, and operational outcomes based on internal and external customers
• Define the operating model that moves the team from project-based execution to outcome-based ownership, with clear intake, prioritization, and delivery cadence.
• Build a strong team through deliberate hiring, training, and retention, developing the engineers you have while adding the capabilities you need.
• Establish engineering metrics and reporting that give the executive team real visibility into velocity, quality, AI adoption, and business impact.

AI Strategy and Adoption

• Own the AI strategy across Nooks, spanning the AI capabilities in our delivered products and the integration of AI into how the company works.
• Drive measurable AI adoption across internal functions, accountable not just for shipping capability but for changing how teams actually operate.
• Rebuild how Nooks captures, structures, and retrieves institutional knowledge so expertise scales beyond the people who hold it.
• Own AI governance for the software portfolio, including data handling, model use, and evaluation, coordinating with IT/Cyber where network security apply.

Government Contract Delivery and Capture

• Own delivery against awarded software contracts, including scope, schedule, technical quality, and customer confidence in our capabilities.
• Run awarded work as a managed line with visible economics, owning cost, staffing, and utilization against the commitment (and EBITA expectations).
• Represent Nooks engineering and AI capability directly to government customers, in delivery reviews and in pursuit conversations.
• Support Growth on software pursuits by shaping technical approach, staffing models, and cost inputs, and by converting delivered work into past performance Nooks can compete on.

Internal Technology Strategy, Platform, and Investment

• Set the technology strategy and architecture roadmap for everything the team builds, including systems that may deploy into customer environments.
• Own the platform our site teams, Operations, and internal functions depend on to manage our spaces, our members, and our customer contracts.
• Make and defend build-versus-buy decisions, integrating commercial systems where they fit and building only where Nooks gains real advantage.
• Build the business case for engineering investment, including headcount, tooling, and vendor decisions, and manage the portfolio against it.

What Success Looks Like in This Role

Software delivery is predictable enough that leadership stops asking for status and starts asking what else the team can take on, with awarded work running against known economics rather than best effort. AI shows up in workflows that measurably change, and in product capability the customer can see, with tangible adoption you can point to rather than describe. The platform our site teams use is in production and reducing work, not sitting in a roadmap. Growth brings you into software pursuits early because your input changes whether Nooks bids and how it prices, and government customers treat you as the credible technical voice for the company. The executive team relies on you for the technology and AI direction of the business, and the plan for how the function scales exists, is funded, and is being executed.

Cross-Functional Expectations

You will work with the CEO on technology and AI direction, with Growth on pursuits and customer engagement, with Operations and the site teams who depend on what you build, with IT/Cyber to manage network and infrastructure dependencies, and with Product on where physical and digital offerings meet. Operations for what your team ships are yours, run in partnership with IT/Cyber. You will also work with Finance on the economics of delivered work and the case for engineering investment. Externally you will hold technical relationships with government customers and manage the vendor and partner ecosystem across the software stack.

The Skillset

• 8+ years in software engineering with progressive leadership responsibility, including ownership of a full engineering or software product function.
• Experience leading software delivery to the USG, with direct exposure to federal customers and the constraints that come with them.
• A Command of modern AI practice, including large language models (LLMs), agentic frameworks, retrieval-augmented generation (RAG), orchestration, and AI governance.
• Experience owning delivery economics, including cost, staffing, and utilization against a fixed commitment, and built the business case for technology investment.
• Experience building and leading an engineering organization, including operating model, hiring, and the shift toward outcome-based delivery.
• Demonstrable experience managing customer and cross-functional relationships at the executive level.

Preferred:

• Experience in defense, national security, or another regulated environment with clearance, compliance, or controlled-data constraints.
• Software capture experience, including technical approach and cost input on federal proposals.
• Experience delivering software for field-based or operational users.
• Active security clearance.

Eligibility & Clearance

Candidates must be authorized to work in the United States. An active security clearance is preferred. All candidates must be eligible for and committed to obtaining and maintaining a U.S. government security clearance as a condition of employment.