As the second founding engineer at Context Systems, you will build the infrastructure that maps every email, matter, and commitment into a unified AI context layer. Working alongside second-time founders, you’ll own the full stack, from frontend to specialized AI systems, ensuring AI tools start with deep, persistent knowledge rather than from scratch.
Founding Engineer at Context Systems
Join Context Systems as the second founding engineer building the 'context layer' for the legal industry. Backed by Daniel Gross and founded by a team of second-time founders, you'll work at the absolute frontier of AI context engineering to transform how law firms handle massive unstructured data. This is a rare opportunity to join a high-velocity team of serial entrepreneurs in London, where you will own the full-stack architecture of a system that provides a perpetual understanding of client interactions. We offer significant equity and high autonomy in a high-urgency environment for builders who value craft and rapid execution.
What's the next step?
Jack finds you jobs at companies like Context Systems. Talk to Jack to get considered for roles that fit what you're great at.
Location
London, United Kingdom
Compensation
Not Disclosed + Equity
Company
Context Systems
Role overview
Context Systems is the context layer for law firms – a perpetual AI operating system that runs in the background, understanding every email, matter, and commitment so that by the time a lawyer talks to their agent, it already knows everything. We’re backed by Daniel Gross and just came out of stealth. Our tagline is “a firm that forgets nothing” – we give law firms answers to questions like “what is my Associate working on?” and “have we dropped the ball on anything this week? Unlike AI tools that start each task as a stranger, Context Systems gives every AI tool the full picture before work begins. Each matter a lawyer works on feeds back into the system, making it more accurate and more personalised to that firm over time. We work with firms like Presidio (#17 globally for ECVC, with a team of just 40).
What you will do
- Architect and build the full-stack infrastructure for a perpetual understanding engine that processes massive volumes of unstructured legal data.
- Develop and integrate AI systems that bridge the gap between raw document context and the tools law firms use daily.
- Own significant product features from conception to deployment, collaborating directly with the founding team in a high-autonomy, high-urgency setting.
Who this is a fit for
- You are an AI-native full-stack engineer who leverages tools like Cursor and Claude Code to maintain extreme shipping velocity.
- You have a proven track record of shipping high-quality code, evidenced by side projects, open-source contributions, or previous founding experience.
- You prioritize “slope over intercept,” demonstrating a rapid learning curve and the ability to solve complex engineering challenges without being reliant on specific frameworks.
Why this role is remarkable
- Join a high-velocity team of second-time founders backed by Daniel Gross, moving from stealth to scaling a frontier AI product.
- Receive a generous equity package, significantly higher than typical startup benchmarks, reflecting your status as a core founding member.
- Work in a radical honesty environment with zero ego, where your engineering decisions directly shape the architecture of context engineering for legal tech.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
Jack’s an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack’s network.
If your profile’s a match and Context Systems wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.