About the role
You’ll be our second engineer, working directly with Caddy’s founders on core architecture, product direction, and execution. If you’re excited about real-time systems, agentic workflows, and building a product you’ll use every day, you’ll have outsized impact here.
You will own large, ambiguous problems end-to-end: from choosing the approach to shipping new features, operating them in production, and iterating based on user feedback.
We work in person out of our SoHo office.
What we’re looking for
- Obsessed with building a product that not only our users love, but that you love and want to use every day
- Can make and defend thoughtful product and technical tradeoffs
- Thrive in ambiguity and default to ownership
- Care about correctness, performance, and user experience
- Move fast and with intention
- Strong opinions, loosely held
What you’ll do
- Own core systems for real-time voice → intent → action workflows
- Design APIs/services for long-running, stateful agent tasks
- Ship user-facing features with strong quality and polish
- Improve reliability, observability, and performance as we scale
- Help set product direction and company culture as the team grows
Our tech stack
Our tech stack is pragmatic and evolving. We care more about strong fundamentals than specific tools.
- TypeScript (required)
- Swift, Objective-C (bonus)
About Caddy
Caddy is building the next interface for AI — a personal, proactive AI teammate that lives in iMessage and works on your behalf across the tools you use every day. Instead of requiring complex prompts or technical setup, Caddy learns how you work and acts autonomously, handling everything from drafting email responses to managing your calendar, Slack, Notion, and more.
Their mission is to make AI feel simple, natural, and useful in the flow of everyday work. While most AI products today still feel like tools for the technical 1%, Caddy is building software that's accessible to everyone — from startup founders to people in theater — without downloading an app or learning a new interface.
Culture
Caddy is a small, high-trust team where everyone has significant ownership, autonomy, and responsibility. All current team members are former founders. The culture is intense, fast-paced, and deeply ownership-driven with a strong emphasis on product craft, speed, and in-person collaboration.
The team works in person from their SoHo, New York office, typically six days a week. They're deeply bought into the same goal: building a product and company they're proud to share with their friends, families, and the world.
Caddy is backed by Y Combinator, Matrix Partners, and prominent angels. The founding team previously built Loom's AI and core product.
Other roles at Caddy
Job details
Salary
$120,000 - $180,000
Equity
0.5% - 1.3%
Location
New York, NY
Experience
0+ years
Funding
Total raised
$500K
Last stage
Seed
Investors
What happens next.
No applications, no recruiter spam. Just the intro.
Confirm the fit
A few questions to make sure this role is the right shape for you. Two minutes.
I pitch you to the company
I write the intro, send it to the founder, and handle the back-and-forth.
A meeting lands on your calendar
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.