Posting record
Open 13+ days
- Caddy's site dates the posting
- Ghostless first sees this listing
- Last checked: still up
How we know
It hasn't been reposted, listed twice, or left up unusually long, and the posting doesn't say it's a talent pool.
Ghostless records the day it first sees a posting, so a repost can't reset its age. This one was already up when Ghostless started tracking Caddy, so its true age is longer.
Last checked Nov 1, 2026.
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Upload your resumeWhat the posting discloses
Not stated: Pay, real vacancy, AI screening.
Why these three
Ontario requires postings from employers with 25 or more staff to state the pay, whether the vacancy exists, and whether AI screens applicants.
Some employers add pay only on their own site. Check the original posting before you rule it out.
Skills mentioned
About the role
About Caddy
At Caddy, we’re building software that makes AI feel simple, natural, and useful in the flow of everyday work. Most AI products today are powerful, but they still feel like tools for the technical 1%. They require the right prompts, the right setup, and too much manual context.
Caddy is building the next interface for AI: personal, proactive, and built for the way people already work.
We are backed by Matrix, Y Combinator and top tier angels.
Culture
We are a small, high-trust team. Everyone has a lot of ownership, a lot of autonomy, and a lot of responsibility. All current team members are former founders.
We work in person from our SoHo, New York office. We’re deeply bought into the same goal: building a product and company we’re proud to share with our friends, families, and the world.
We work hard. The pace is fast, the problems are messy, and the standards are not for everyone.
The Role
We’re looking for full-stack engineers who are extremely technical, product minded, and care deeply about craft.
- You will own large, ambiguous problems end-to-end: choosing the approach, building the system, shipping to users, and iterating based on data and feedback.
- Caddy sits at the frontier of memory, personalization, and proactive AI. You’ll work on problems that do not have obvious answers yet, from agent reliability, and context retrieval to user trust, integrations, and new interaction models.
- Experience with TypeScript
What we are looking for
- Systems Builder: You build scalable systems, not vibe-coded features. You think clearly about how problems evolve as usage grows, and you know when to move fast versus when to build the right foundation
- Strong opinions, loosely held: You care a lot about the work and the output. You’re direct, thoughtful, and willing to disagree, but it never gets personal.
- Determination: Startups are messy. The hours are not for everyone. You are excited by the intensity required to build something excellent, and you want to help build a generational company.
- Product Taste: You care about how the thing feels, not just whether it works. You notice details. You want users to feel like Caddy is simple, useful, and alive.
Process
- Phone screen
- Technical review
- Onsite review
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