NYC: (4) Senior Product Designers @ mission-geared HR Tech company

Shape the Future of Benefits + Payroll for SMBs!

Location: 2–3 days/week hybrid onsite in FiDi (NYC) with sweeping bay views

Comp: $166-214K base + equity (pre-IPO options) + unlimited PTO 

Visas: Sorry, no visa sponsorship or transfers available at this time

Our client, a thriving, established Benefits / Payroll tech company focused on empowering small to medium sized businesses (SMBs), is hiring multiple Senior Product Designers across several interconnected product and service experience areas.

It’s a great opportunity to be exposed to multiple project areas at once - it’s more bang for your interviewing buck!

You’ll join a thoughtful, design-mature, ~50-person Experience Design team led by one of our favorite VP Design leaders. He’s highly respected, deeply human, sharp, funny, and skilled at building a design culture where craft, systems thinking, service design, and real cross-functional partnership matter.

This is a broader Senior Product Designer search, which means that you’ll have the opportunity to learn about multiple problem spaces and be considered for the areas where your strengths, interests, and experience can create the strongest long-term impact.

It’s a mutual selection process: the company will get to understand how you think, work, and design across complexity, and you’ll get a fuller view of the range of product and service experiences being shaped across the company before the final match is made.

About the company:

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 Benefits / Payroll platform tech company in an exciting stage of substantial but responsible growth, with great name recognition. They provide SMBs, including many tech startups, high-quality, enterprise-level health insurance, payroll, payments, and HR tools that smaller businesses and their employees wouldn’t otherwise have access to.

They’re known for a standout culture rooted in honesty, openness, integrity, friendliness, no-ego, and inclusion. “Collaboration” isn’t just a word on a cheesy poster in a hallway. It represents their values at their core.

Their cred:

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

They’ve been in business for 14 years and are an important player in the HR Tech industry. They’ve secured significant funding from top VCs including Bain, Thrive, FirstMark Capital, and Union Square Ventures.

They’ve expanded into global markets, grown consistently and intelligently year over year, and are adding a broader suite of products to their already well-known core platform.

What’s happening there in Design:

They brought in their first-ever VP Experience Design, who we’ve known for years and absolutely trust. His arrival was a strong signal of the company’s growing investment in Design and respect for the discipline.

We’ve helped this VP grow his teams over many years and have seen firsthand how much his designers trust him. He’s empathic, strategic, supersmart, and a real thought leader. Plus, he has a great sense of humor, which makes for a super enjoyable work vibe! 🙂

Design here is increasingly focused on the full service experience: not just isolated screens, but the interconnected frontstage and backstage moments that shape how employers, employees, internal teams, partners, and systems all work together.

This is a great environment for designers who understand that experience goes beyond interface, and that design value often comes from helping teams make better decisions. The most successful designers here are systems thinkers who can design across connected steps, workflows, operational realities, and product touchpoints, while still bringing strong craft and attention to detail.

The work on deck:

You may work on experiences connected to benefits, payroll, payments, purchasing, employer / employee workflows, internal operations, service layers, compliance, or other deeply interconnected parts of the platform.

Some work may be more customer-facing. Some may be more operational. Much of it touches both. That’s part of what makes the work interesting here: the company designs for complex, integrated human / software service delivery, where products, people, policies, workflows, and business needs all connect.

What you’ll get to do in this role:

• Design across the full product development lifecycle, from discovery through launch, adoption, measurement, and iteration
• Work on complex, interconnected product and service experiences that support SMB employers, their employees, and the internal teams who serve them
• Collaborate closely with partners in Product, Engineering, Research, Data, Content, Marketing, Operations, Support, Compliance, and other design areas
• Map complex workflows, information structures, user journeys, service moments, and dependencies across systems
• Use research, data, experimentation, and stakeholder input to understand user behavior and frame design problems clearly
• Create flows, wireframes, conceptual models, prototypes, high-fidelity UI, interaction patterns, and design-system-informed solutions
• Use artifacts and storytelling to build shared understanding, align non-design audiences, and guide teams toward clear decisions
• Contribute to a design culture where designers show work early and often, give thoughtful critique, care about craft, and balance user needs with business and technical constraints
• Think about AI not just as a tool, but as a material in the product experience: how it works, where it adds value, what logic sits behind it, and how it can help teams create better software and service experiences

The ideal candidate has:

• 6+ years of relevant Product Design experience, with strong UX and visual UI craft
• Experience designing complex B2B, B2B2C, enterprise, SaaS, FinTech, HR Tech, Benefits, Payroll, EdTech, HealthTech, or similarly workflow-heavy products
• Experience designing for complex, integrated human / software service delivery, ideally across multiple user types, systems, or operational layers
• Strong systems thinking and the ability to understand how one product decision affects the broader experience
• Experience with service design, journey mapping, workflow mapping, information architecture, or visual modeling of complex concepts
• A portfolio that shows launched product work, clear problem framing, collaboration process, final solutions, and measurable outcomes where possible
• Equal comfort moving from ambiguous discovery into concrete flows, prototypes, and polished UI
• Strong visual design craft, including typography, hierarchy, layout, interaction patterns, and attention to detail
• Ability to use qualitative and quantitative research and data to inform design decisions
• Experience contributing to or extending design systems
• Strong communication skills and comfort explaining design rationale and tradeoffs to cross-functional partners
• A collaborative, low-ego working style and the instinct to share early, invite feedback, and keep work moving
• Curiosity about AI and how it is changing both design workflows and the products designers are creating

Nice to haves:

• Experience designing for SMBs or small business owners
• Experience with insurance, fintech, benefits, payroll, HR tools, compliance, payments, healthcare, or other regulated / high-trust product areas
• Experience designing some or all of the following: service workflows, internal or admin tools, operational products, products with heavy customer support / operations dependencies
• Experience launching AI-enabled product, not just executing AI-assisted prototyping work
• Information architecture skills

TO APPLY:

Apply here online, or email us at team (at) joanneweavergroup.com with your resume, portfolio, openness to 2–3x/week onsite in NYC, and desired full-time comp range.

We'll get back to you if it looks like a strong match!

Not for you but know someone great in NYC?

$1,000 Referral Bonus!

If you know fantastic Midlevel or Senior Product Designers in NYC that you think could be great for this client, please drop their name to us via team (at) joanneweavergroup.com

We give up to a $1,000 referral bonus for the long-term placement of your peeps, and lots of thanks!