Caddy
AI & Machine LearningDirect Rippling career site

Member of Technical Staff

Location
New York, NY · On-site
Job type
Full-time
Level
Mid-level
Listed
30 days ago

Skills & highlights for this role

  • TypeScript
  • full-stack development
  • scalable system design

Also useful

  • AI agent systems
  • context retrieval

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
  • About Company ---

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.

Read the original posting

From Caddy's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

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Common questions

Where is the Member of Technical Staff job at Caddy located?

This Member of Technical Staff position at Caddy is located in New York, NY (On-site). Always check Caddy's application page for specific state eligibility or relocation policies.

What qualifications are required for Member of Technical Staff at Caddy?

For the Member of Technical Staff role, Caddy highlights experience with TypeScript, full-stack development, scalable system design. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Member of Technical Staff position at Caddy?

This listing links directly to Caddy's Rippling application page. You can apply directly on Caddy's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Rippling application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.