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Product Designer @ High-Growth Accounting AI Startup
Chicago, IL
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Role: Product Designer (Agent-Native UX)

Location: New York City, NY (Flatiron — On-Site, 5 Days/Week)


Our client is an AI-native enterprise software company building agent-driven systems that execute real, high-stakes professional workflows. Their platform enables humans and AI agents to collaborate inside production environments, redesigning how complex work is completed, verified, and trusted.


Backed by top-tier investors and operating with exceptional speed, they are scaling rapidly while defining a new interaction paradigm between humans and autonomous systems.


Position Overview:

The Product Designer will report directly to the founders and product leadership and will define how humans and AI agents collaborate through interfaces that are both visible and invisible.


This is not incremental design work. You will design systems for a future where AI reasons in real time, breaks traditional UX assumptions, and dynamically assembles interfaces in production. You will prototype, ship, and iterate continuously—often designing 12–18 months ahead of what exists today.


This role is ideal for a systems-oriented designer who ships quickly, thinks from first principles, and thrives in high-bandwidth, in-person collaboration.


Key Responsibilities:

  • Build Agent-Native Experiences
  • Design interactions between users and autonomous agents across multiple product surfaces
  • Invent agent-ready UI primitives that can be dynamically composed in real time
  • Partner closely with engineering to integrate agents into live workflows
  • Ship experiences where humans and AI agents meaningfully collaborate
  • Develop Deep User Empathy
  • Perform real domain-specific work inside the product to understand workflows firsthand
  • Learn how users build trust, manage risk, and make decisions in high-stakes environments
  • Validate designs with real users doing real work
  • Shape Long-Term Product Vision
  • Work directly with founders to sketch the product vision multiple years out
  • Translate abstract strategy into shipped, production-ready experiences
  • Own the design roadmap in alignment with company priorities
  • Learn at Warp Speed
  • Rapidly master new domains, evolving LLM capabilities, and emerging AI-native UX patterns
  • Convert insights into decisive design choices within days—not months


Qualifications:

This role is for a designer who is equal parts builder, thinker, and executor.


You likely fit if you:

  • Have 4–8 years of experience designing complex SaaS or AI-driven tools
  • Have owned at least one 0→1 product launch end-to-end
  • Think from first principles and enjoy rebuilding systems from the ground up
  • Actively prototype with LLMs and use AI tools daily in your workflow
  • Move from rough sketches to high-fidelity Figma independently
  • Ship in weeks, not months, and are comfortable iterating in production
  • Are NYC-based and excited about a 5-days-in-office environment


This role is not for you if:

  • You need remote or hybrid flexibility
  • You prefer structured environments with established patterns
  • You prioritize perfection over shipping
  • You have limited hands-on experience with AI tools in design
  • You want a strict ~40-hour workweek or clearly bounded scope


What they offer:

  • Market-competitive salary for a Series A stage company
  • Meaningful equity at an early inflection point
  • Full health, dental, and vision coverage
  • 401(k) with company match
  • Unlimited PTO plus a full week off at the end of the year
  • Professional development budget
  • High-ownership role with direct founder access
  • A beautiful NYC office and a deeply collaborative, in-person culture


Interested?


If you’re reading this thinking “this is exactly me”, please DM me on LinkedIn!🔗

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