NYC: Product Designer, Benefits (Visual UI leaning)

@ high-growth benefits / payroll tech company helping SMBs

Location: 2 days/week onsite in NYC, with sweeping river views!

Comp: $127,000 to $160,000 base + pre-IPO equity

Sorry, no visa transfers available at this time.

The client:

Chances are, if you've worked for a startup or an established small-to-medium-sized business, you're probably already familiar with our client!

They're a late-stage, b2b2c Benefits / Payroll tech company with great name recognition in the tech space.

They’re also in an exciting stage of massive growth, and as a part of that growth, they’ve embraced AI in an intelligent way, both within their own Design process, and instilling AI into the products they make.

They provide SMBs, including many in the tech industry, high-quality, enterprise-level health insurance and payroll tools that smaller businesses and their employees wouldn’t otherwise have access to.

They also have an incredible culture, rooted in honesty, openness, integrity, friendliness, no-ego, and inclusion. “Collaboration” isn’t just a word on a cheesy poster in their hallways; it’s their values at their core.

It’s truly a dreamy place to work, and this is a golden opportunity to join a high-impact Benefits team working on some of the most meaningful, human, and complex parts of the product experience.

Their cred:

Fortune magazine named them to their Best Workplaces in New York list 5 times, and they’re also on BuiltIn’s list of “NYC Best Large Companies to Work For.”

They’ve been in business for 10+ years and are an important player in the $40B HR Tech industry. They’re secured $160M in funding from top VCs including Bain, Thrive, Union Square Ventures.

Their star is rapidly rising; it’s a great time to get in the door! They continually expand into global markets and have grown consistently and intelligently year over year, including during times when many other companies were laying people off.

They’re currently at 1300 total employees, with 35+ Designers, and have doubled their Product org in the last 2 years.

What's happening there in Design:

We've known their VP of Design for many years and adore him. Since he joined this company 2+ years ago, he's steered Design into one of the most influential disciplines in the company, with reach and impact that extends well beyond the org chart.

He thinks expansively about the present and future of Experience Design, pushing past the screen and into the full gestalt of the user journey, whether that person is a customer or a colleague.

They are using AI quite a bit, in intelligent ways, both in their own Design process, as well as making AI-enabled tools. They gravitate towards designers who embrace new technology and have gotten their feet wet building with AI.

The Role:

They're looking for a full-time Product Designer to help scale their Benefits experience.

While the role is full stack UX / UI, they’re looking for someone with an especially lovely Visual UI aesthetic, with a real sense of craft.

The ideal candidate is on the more seasoned end of Midlevel, ie, 4-5 years of experience and can work fairly autonomously, yet highly collaboratively.

The Benefits team’s mission is to provide peace of mind to admins, members, and their families. They help businesses access enterprise-level benefits they may not otherwise be able to offer, including high-quality health insurance, financial wellness support, and resources for major life events and unexpected moments.

This is a role for a strong, thoughtful Product Designer who can move between big-picture systems thinking and polished UI execution. You’ll work on complex, content-heavy, highly regulated workflows, and translate them into experiences that feel clear, simple, and trustworthy.

You’ll be designing for dual workflows across the same ecosystem, including admin experiences and member experiences. That means understanding how one decision or interaction can affect multiple user types, and how to create coherence across both sides of the experience.

Strong visual craft really matters here. You should have a refined sense of UI, typography, layout, interaction detail, and brand expression, and be able to bring complex experiences to life in a way that feels elegant, usable, and consistent.

You should also be someone who shares work early and often. This team values designers who are open, collaborative, curious, and actively looking to make the work better through critique, feedback, and partnership.

You'll be:

Designing across the full product development lifecycle, from discovery and conceptual thinking through delivery, launch, iteration, and refinement

Partnering closely with Product, Engineering, Research, Marketing, Data Science, and other Designers to define problems, explore solutions, and deliver high-quality work

Conducting and collaborating on user research, usability testing, data analysis, rapid prototyping, and experimentation

Creating polished, high-craft UI and interaction designs in Figma

Using AI tools as part of your design workflow, or bringing a strong working knowledge of how tools like VISO, Figma Make, Claude Code, and related platforms can support modern design practice

Working with and contributing to their design system, with an eye toward consistency, quality, scalability, and efficiency

Sharing work in design sessions, actively seeking feedback, and contributing thoughtful critique to help elevate the broader team

What They're Looking For:

4+ years of Product Design / UX Design experience designing web and mobile-based applications

Strong visual design and UI craft, with solid UX skills too, and excellent attention to detail across layout, hierarchy, typography, interaction patterns, and brand expression

Experience designing complex, content-heavy, or regulated workflows, ideally in benefits, healthcare, insurance, fintech, HR tech, or a similarly complex product environment

Experience designing for multiple user types within the same ecosystem, especially admin and member/customer workflows

Strong communication and collaboration skills; comfortable working closely with - and building world-class relationships with! - PMs, Engineers, Researchers, Data Scientists, Marketers, and other cross-functional partners

Working knowledge of AI design tooling and how it can support design exploration, prototyping, workflow acceleration, or product thinking

A portfolio of real-world product design work, with case studies that clearly show the problem, your process, design decisions, final outcomes, and business or user impact

Bonus points for:

Experience in healthcare, benefits, insurance, marketplaces, or other highly regulated / multi-sided product environments

Portfolio examples involving enrollment flows, benefits selection, onboarding, eligibility, or similarly complex decision-based workflows

Experience designing for products with international needs, including localization, compliance complexity, or global user considerations

Location:

2 days/week onsite in NYC, with sweeping river views!

Comp:

$127,000 to $160,000 base + equity in the form of pre-IPO options

Benefits:

World-class health insurance, flexible PTO, a dog-friendly office, 16-week parental leave, full or partial coverage for Citibike, Talkspace, and fitness memberships, ERG groups, continued learning resources, wellness room, and more.

TO APPLY:

Apply here online, or email us at team@joanneweavergroup.comteam@joanneweavergroup.com with your resume, portfolio, openness to 2x/week onsite in NYC, and desired comp range.

We'll get back to you if this looks like a good fit for you!

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$1,000 Referral Bonus!

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