Head of Engineering (Contract-to-Hire)

About Bundle

Bundle builds AI-powered software for the construction supply chain - a $2.3 trillion industry that still largely runs on phone calls, PDFs, and spreadsheets, where the overwhelming majority of projects run over time and over budget because materials don't show up right.

We've already proven the model. Our materials marketplace is live and revenue-generating on 8-figure annual transaction volume, running a catalog of 300,000+ SKUs with proprietary B2B pricing. That's the foundation. What comes next is bigger: an AI-powered takeoff and quoting product, and a broader push to automate the parts of the supply chain that no one has managed to make work — estimating, code compliance, catalog intelligence, supplier communication, and quoting for custom skus.

We're a small, venture-backed team (Urban Innovation Fund, Slauson & Co., Alumni Ventures). Learn more about our mission at www.bundle.build and www.bundletakeoff.com

Why this role exists

We're hiring the person who will lead the technical side of the next evolution of the company.

The mandate is forward-looking. Our takeoff product and the AI-heavy work around it are where the business is going, and we need a technical leader to own that direction: to decide what we build, to build it, and to turn our early AI workflows into a real product surface that customers depend on. The existing marketplace already works and generates revenue - your job there is to keep it healthy and stable in the background, not to rebuild it. The energy goes into what's next.

This is not a role where you join an established engineering org and pick up a well-trodden corner of the codebase. You'll be the senior technical owner working alongside one senior offshore engineer and directly with the founders, with unusual influence over technical direction and unusual proximity to the decisions that determine where the company goes. If you want to help shape a company's next chapter from the inside - and you're excited by AI applied to a massive, un-modernized industry - there are few better seats.

What you'll own

Lead the next evolution of the product. Own the technical direction of our takeoff and quoting product and the AI-driven supply chain work around it.

Own and expand the AI/automation layer. We already run LLM-driven workflows for product data enrichment, catalog matching, supplier communications, and quote processing, exposed in part through an MCP server. This is the heart of where we're going, and there is enormous room to expand what's automated and turn it into durable product.

Be the technical voice in business decisions. Advise the founders on what's feasible, what it costs, and what we should and shouldn't build as we expand. Help set the technical strategy for the next phase, not just execute it.

Keep the platform healthy. Our live marketplace transacts real money every day. Production stability, incident response, deployments, monitoring, and the load-bearing integrations (supplier data feeds, payments, email, CRM, delivery tracking) need to keep running smoothly - pragmatically and without drama - so the team's attention stays on what's next.

Absorb the existing system. Understand the current system and enable the current products to maintain themselves as much as possible while you push forward.

What we're looking for

Required

• 7+ years building and running production web applications, with meaningful time as a senior or lead engineer
• Production experience with LLM-based features — prompt design, structured output, evaluation, and a realistic sense of where models work and where they don't. You've shipped AI into real products, not just prototyped with it.
• A builder's instinct — you're energized by defining and shipping new product, and you can lead technical direction, not just take tickets
• Strong Python, with deep production Django experience
• Solid AWS experience — you can navigate our infrastructure, deploy, debug, and manage cost without a DevOps team behind you
• Relational database fluency (PostgreSQL) — schema design, query performance, migrations on live data
• Ability to work independently, prioritize ruthlessly, and communicate clearly with non-technical founders
• Comfort inheriting an existing production system and stabilizing it enough to build on top of - you can keep something running while you focus on what's next

Valuable

• Model Context Protocol (MCP) or agentic tooling experience
• Search and catalog infrastructure at scale — entity resolution, fuzzy product matching, deduplication
• Modern JavaScript/TypeScript front-end work (React / Next.js)
• Mobile app experience (we ship iOS and Android)
• Async task processing (Celery or similar) and background job reliability
• Payments and financial workflows (Stripe or equivalent), including the correctness and reconciliation demands that come with money
• Third-party API integration work at volume (Google Workspace, CRM, logistics/tracking providers)
• Monitoring and error tracking (Sentry or equivalent) and a genuine instinct for operational hygiene
• E-commerce, marketplace, B2B procurement, or supply chain domain background
• Construction or building products industry exposure

Who this is right for

You want to build. You're excited by AI applied to a huge, un-modernized industry, and you want to be the person informing what gets built and then making it real. You're comfortable being the most senior technical person in the room and equally comfortable saying "I don't know yet, give me a couple days." You're pragmatic about the parts that just need to keep working — you'll keep the existing system stable without letting it consume you — because your attention belongs on what's next. You like breadth: an LLM pipeline one day, product direction the next, a production issue the day after. You're motivated by ownership and impact more than by title or team size.

Who this is not right for

If you need well-defined tickets, an established platform team, or a mature engineering process, this will frustrate you. If you only want to maintain what already exists and have no interest in defining and shipping new product, this isn't the role — the whole point is leading what comes next. And if your instinct on inheriting a codebase is to rewrite it from scratch, we're not a fit — we need someone who can keep an imperfect system serving customers while building the future on top of it.

Compensation and Benefits

• $120,000 - 150,000 annual salary
• Competitive equity package on conversion to full-time hire
• 401K retirement plan
• Health, vision, dental insurance
• WFH annual stipend

How to Apply

Submit an application on Wellfound with:

• A short note on something you built or a technical direction you led — ideally involving AI/LLMs in production — what you set out to do, and how it turned out
• Your resume or LinkedIn
• Your preferred engagement structure and availability