Founding Product Engineer

The Opportunity

Commercial construction is a $2.4T industry still run on spreadsheets, WhatsApp threads, and gut instinct. Shackleton is changing that, building the first AI operating system for commercial general contractors and automating everything from bid management to field execution to financial close.

We know this industry because we have lived it. Our founding team built and scaled Ernest, a self-performing general contractor, to $30M ARR before building Shackleton on top of what we learned. That operator credibility is our unfair advantage, and it is why we win.

We closed our seed round led by Battery Ventures with participation from Trust Ventures, Correlation Ventures, Brick and Mortar Ventures, Act One Ventures, Motivate Partners, Brainstorm VC, and Thayer. Now we are hiring our founding US engineer to deepen the product and prove the engine at scale.

The Role

This is the first US-based engineering hire on a team of 10, including engineers, designers, and QA. You will not be one of many engineers slotting into an existing org with a backlog handed to you. You will work directly with the CPO and founding team to take ambiguous, high-leverage problems and ship them end to end.

Because you are early and customer-facing, the role is deliberately two-sided. You will build the core product, and you will go deep with our early enterprise customers, owning the integration and converting real field and ops pain into product. If you want to define both the product and the engineering culture of a company at the ground floor, this is the seat.

What you will own

• Build end to end: own features from design through deployment, taking undefined problems and breaking them into shippable solutions with minimal scaffolding.
• Architect the foundation: make and influence the technical trade-offs that will compound for years, providing system-wide context for future technology choices
• Multiply with AI: drive full-cycle product development through LLM harnesses (i,e Claude Code/ Codex), from spec to execution to testing, and build the internal tooling that lets the whole team do the same.
• Set the standard: advocate and enforce engineering best practices, then encode them into reusable automation rather than tribal knowledge.

What We Are Looking For

Engineering background

• Experience: 5 years developing user-facing web applications, with production experience across the stack.
• Technical mastery: Experience in React and TypeScript on the front end, and production experience with Go and PostgreSQL on the back end. Mobile experience is a plus.
• Ambiguity management: a proven ability to navigate undefined problems and break them into actionable solutions with minimal guidance.
• Architectural vision: demonstrated ability to make or influence critical technical trade-offs with long-term implications.

AI-native engineering

• Code harness fluency: hands-on experience using agentic coding tools such as Claude Code and Codex beyond prompts, using loops, goals, skills, agents and subagents
• Automation building: experience creating skills, agents, and sub-agents that automate and accelerate full-cycle engineering workflows
• Judgment over output: you know where AI accelerates you and where it does not, and you review, test, and own everything that ships under your name. 

Product and customer sense

• Product thinking: a strong track record of shipping features that measurably improve the customer experience, with a desire to own outcomes rather than tickets.
• Customer instinct: experience working directly with customers and customer operations to accelerate product thinking, and genuine willingness to sit in the field with general contractors to understand the problem before building.
• Domain curiosity: construction is complex. You dig into the product, the industry, and the customer's world without being told to. Construction or proptech experience is a plus, not a requirement, and we will teach the domain.

Who you are

• Builder mentality: you get energy from creating, not just maintaining. You have shipped things end to end and set up your own tooling and process.
• High ownership: you do not wait for a PM, a designer, or a manager to unblock you. You desire to be in an environment where you are empowered to figure it out.
• Coachable but opinionated: you bring an informed point of view and push back constructively, then execute once a decision is made.
• Low ego, high standards: you will do unglamorous work when it is what the stage demands, because you understand what is at stake.

Why Now

Construction has been one of the last major industries to see meaningful software adoption, and that is changing fast. We are at the beginning of a multi-decade shift, we have the operator credibility to win trust in a relationship-driven market, and we are building an engineering team that uses AI as a force multiplier from the first hire forward. You will set the technical foundation and the culture that every engineer after you inherits.

If you build end to end, treat AI as a core part of how you work, and want to shape both the product and the customer alongside it, this is the seat.