Senior Product Designer

Medal, Highlight, & General Intuition•New York City, NY

13d•Onsite

About The Position

Highlight is a cutting-edge AI desktop assistant that sees and hears what you see and hear, designed to enhance productivity by seamlessly integrating with your workflow. We empower users to interact with any application using text and voice commands,, eliminating the need to switch between tools. We raised $13M from Conviction and Khosla. The Role We’re hiring a Senior Product Designer with technical skills to own visual craft and product design at Highlight. You’ll help define how people interact with AI beyond chatboxes, and your work will be visible immediately in the product. If successful, your designs will be the reason people screenshot Highlight, share it, and talk about how innovative it feels. You’ll take raw interaction ideas, half-formed concepts, and functional wireframes and turn them into interfaces that feel inevitable, futuristic, and obsessively polished. This role is about execution at the highest level: pixels, motion, transitions, hierarchy, and interaction details that make complex AI systems feel simple, powerful, and delightful. You’ll work directly with product, and engineering to bring new interaction models to life fast – often going from idea to high-fidelity prototype in hours, not weeks. This is a hands-on role. You’ll design and prototype constantly, push the team toward higher taste and sharper decisions, and set the bar for what “great” looks like in AI-native software. Note: this is an on-site role, requiring five days a week in our San Francisco or NYC office.

Requirements

You have shipped products users obsess over
You are exceptional at turning rough interaction concepts and wireframes into polished, production-ready interfaces
You can’t get enough of micro-interactions, animation, and interaction details that elevate the entire product
You are deeply plugged into state-of-the-art UI and actively experiment beyond existing design conventions
You’ve independently designed and shipped work at the level of the Dia (Mac) onboarding, Lapse (iOS), or corner maps (iOS). That level of craft and product judgment is the baseline for this role. Familiarity with work like this is expected.
You can prototype advanced interactions quickly, and are either technical yourself or fluent with tools like Cursor or Claude Code to realize ideas without waiting on others
You have experience with designing AI-native interaction patterns
You send us your work and it clearly wows us
Ownership mentality (no task is too small for you) – it’s all hands on deck here and we need everyone rowing the boat.
Excellent communication skills and a collaborative mindset – we’re extremely lean so we’re looking for a team player who works well with others.
Type-A tendencies: maybe you’re extremely detail-oriented. Or maybe you take pride in shipping high-quality products. Whatever it is you do, you give it your all.
Must be based in or willing to relocate to San Francisco or NYC – although we’re flexible with days off & schedules, we have a 100% in-office culture during the week.
Hustle is expected, grit is required.

Responsibilities

Own visual and interaction quality across Highlight’s product
Regularly talk to users, find creative solutions to their problems, and incorporate them into your designs
Partner closely with the Head of Design to translate interaction concepts, product direction, and rough wireframes into confident, opinionated, high-fidelity UI
Collaborate daily with engineers to bring polished interfaces, motion, and micro-interactions into production
Rapidly prototype AI-native interaction models, through click dummys and in code, often moving from idea to testable prototype within hours
Design and refine micro-interactions, animations, transitions, and layout systems that make complex AI behavior feel intuitive and delightful
Push beyond existing UI conventions and help define new patterns for how users interact with AI systems
Set and uphold a high bar for visual craft, consistency, and accessibility across the product