Head of Engineering

We are an AI-first enterprise software company building intelligent infrastructure for organisations with complex contracts, recurring vendor spend, and high-volume financial operations.

Our platform deploys autonomous AI agents that connect contractual obligations to invoices, payments, and underlying financial systems. By automating the flow of information across traditionally siloed tools, we help large enterprises improve accuracy, reduce manual work, and prevent costly billing discrepancies.

The company is seed-stage, has experienced rapid early growth, and is expanding across customers and geographies. Our customer base includes major real estate owners and operators in the United States, Ireland, and Canada, collectively representing more than $75 billion in assets under management.

We are supported by experienced operators, entrepreneurs, and investors, including founders who have built and exited successful companies.

The Challenge

Large institutional operators often manage thousands—or tens of thousands—of assets through fragmented systems. Contract-management tools, accounts-payable platforms, invoice workflows, and finance systems were rarely designed to communicate effectively one another.

That fragmentation creates substantial operational friction:

• Teams spend significant time reconciling contract terms against invoices.
• Pricing adjustments, escalation clauses, and service-level obligations can be overlooked.
• Financial leakage compounds across large portfolios and recurring vendor relationships.

Our platform serves as an intelligence and automation layer across these systems. It extracts and interprets contract terms, applies commercial rules, verifies invoice accuracy, and flags or resolves exceptions before payments are processed—reducing the need for manual intervention.

Although the business initially focused on residential real estate, the underlying technology applies broadly to enterprises with complex vendor agreements and recurring spend. Relevant verticals include telecommunications, utilities, logistics, multi-location retail, and other asset-heavy or contract-intensive industries.

The Opportunity

The company has reached an important stage: the product is validated, customer adoption is increasing, and new capital has recently been secured to support the next phase of growth.

We are looking for a hands-on Head of Engineering to establish and lead the company’s technical direction as the platform, team, and customer base scale.

This person will own the engineering vision, make foundational architectural decisions, recruit exceptional technical talent, and ensure the company can deliver reliably for sophisticated enterprise customers.

This is a high-impact leadership opportunity with the influence and ownership typically associated with an early technical co-founder. You will work directly with the CEO and a small, experienced founding team, helping shape not only the product and architecture, but also the engineering culture and hiring strategy.

Core Experience

• Significant hands-on software-engineering experience, including shipping and operating production systems at meaningful scale.
• The technical depth to review code, challenge architectural choices, guide implementation decisions, and earn credibility with strong engineers.
• Experience in an early-stage or scaling startup environment, with an understanding of how to move quickly without compromising customer trust, reliability, security.
• A track record of building, hiring, and leading engineering teams, including setting a high talent bar and creating a culture of ownership and accountability.
• Experience developing production-grade AI-enabled products, including areas such as retrieval-augmented generation, LLM orchestration, model evaluation, quality monitoring, human-in-the-loop workflows.
• Background designing and operating data-intensive systems that reliably process large volumes of structured and unstructured information.
• Familiarity with enterprise software requirements including integrations, security, compliance, multi-tenancy, auditability, permissions, and operational reliability.

Preferred Experience

• Experience in fintech, proptech, legaltech, procurement technology, accounts payable, contract management, financial automation, or another document-heavy enterprise domain.
• A history of helping take a product from early customer traction into a more mature stage of growth and scale.
• Experience at a venture-backed or growth-stage company.
• Strong backend and infrastructure expertise, particularly in data pipelines, distributed systems, search, and workflow orchestration.
• Familiarity with technologies such as Node.js, TypeScript, PostgreSQL, Elasticsearch, AWS, and/or Google Cloud Platform.