Founding Software Engineer

Cypress

Running a business today means operating in one world and understanding in another. The owner lives in a stream of real-world events — deliveries, staffing, inventory, customers — context-switching into spreadsheets, dashboards, and reports to make sense of the data. These two realities never quite line up. Cypress collapses the distance between business reality and understanding.

We are building a generational company to enable the future of ownership. Our platform continuously models a business as it runs, constructing a living representation that agents can act on and owners can collaborate with. The result is something that hasn't existed before: businesses that understand themselves. This changes who can own a business, how those businesses are operated, and how far they can go.

Cypress Labs is backed by top-tier venture capital and a roster of angel investors with operational expertise. Founded by Spencer Wilson (MIT, Marshall Scholar, UCL neuroscience PhD, previously Ctrl-Labs and Trisk Bio) and Josh Hone (first commercial hire at bootstrapped Quorum, COO at venture-backed Column).

We're working in person in London.

The Role

We're building a system that autonomously constructs, refines, and reasons with mathematical models of real businesses, in order to simulate, plan, decide, and act. You'll bring this system to life by writing software across the entire stack, every day.

You'll work on whatever needs the most attention: infrastructure, data pipelines, integrations, agent orchestration, domain modeling. You'll work directly with early design partners (real business owners, real operations) to close the gap between what we've built and what they need. You'll inject your opinions into architecture and strategy alongside the founders.

What You Will Do

• Extend the core platform: event sourcing, domain modeling, agent orchestration

• Ship, operate, monitor, maintain production infrastructure

• Build AI agent capabilities: tool design, context assembly, sub-agent architectures, evals

• Integrate external systems: POS, accounting, labor scheduling, weather, banking APIs

• Onboard new merchants, diagnose issues, and translate operational needs into system capabilities

You Bring

• Experience shipping production software at an organization where craft and tempo are taken seriously. NB: we are open to a broad range of experience levels if your work speaks for itself and we see clear indications of high learning rate.

• Range across the stack. You've worked across backend, infrastructure, and data layers, and you're quick to grok the unfamiliar.

• Craft in code. Clean, concise, well-reasoned. Your instinct is to simplify.

• Systems thinking. You reason about how components interact, where state lives, how data flows, and what breaks under load or drift.

• Comfort with math. You don't need to be a mathematician, but stochastic differential equations, Bayesian inference, and Monte Carlo methods shouldn't scare you.

• AI-native engineering. You've built with LLMs beyond wrapper apps: systems where AI is tightly integrated with structured tools, domain logic, and feedback loops.

• High agency. Ambiguity energizes you to find clarity.

• Customer instinct. You're comfortably talking to business owners, dealing with messy real-world data, and translating evidence into engineering priorities.

Why Us

• Cypress is an unusually ambitious technical problem. Autonomously modeling real businesses, running in production, under real constraints. If you want to build agents that matter rather than demos, this is the place.

• Founding-team equity and direct ownership of the stack. You'll inject your opinions into every technical decision alongside the founders.

• Our team will stay small, and our ambitions will stay big. We aim for a high revenue-to-headcount ratio and a high-trust, high-ownership culture.

• Backed by a top-tier venture firm and an angel roster of experienced operators. Product is already working with early design partners.

Compensation

£100k to £155k base, depending on experience. Meaningful equity reflecting a founding role.

Apply

Apply through Ashby with a resume. If you have side projects, open source, or anything that shows how you think and build, include it.

Read our recruiting privacy notice for how Cypress uses your application information and how to exercise your privacy rights.

Compensation: £100K – £155K • Offers Equity

• • £100K – £155K • Offers Equity

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