Staff Product Designer, Contractors

Gusto • San Francisco, CA; New York, NY • 1m ago

Why This Job is Featured on The SaaS Jobs

This Staff Product Designer role sits in a mature SaaS product area where design decisions directly affect business critical workflows for paying and managing contractors. In the SaaS ecosystem, contractor management is a domain where product quality is measured in clarity, trust, and repeatability across many edge cases, making it a strong proving ground for platform level design leadership. The emphasis on an AI native design practice also reflects a broader shift in SaaS teams toward faster prototyping and tighter learning loops.

From a SaaS career perspective, the role offers sustained exposure to cross functional product development across product, engineering, data, legal, compliance, and support. That mix is especially valuable in SaaS because it builds the muscle for designing within real operational constraints while still improving usability and outcomes. Leading foundational shifts to an established product also develops durable skills in systems thinking, prioritization, and iterative delivery that translate across B2B platforms.

This role is best suited to a senior individual contributor who prefers owning a problem space end to end and influencing direction through craft and partnership rather than people management. It fits someone comfortable making decisions amid ambiguity, working across stakeholder groups, and treating AI as a practical part of daily design work, not a side project.

The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.

Job Description

About Design at Gusto

Design at Gusto is made up of over 80 creative, collaborative people who care deeply about our mission to empower small businesses and their employees. We're a cross-functional group that is always looking for opportunities to build understanding and empathy for the people who use Gusto. We don't care much about swim lanes and though we care deeply about quality and craft, we are never precious about it.

We work closely with cross-functional partners in Product, Engineering, Data, and Marketing to design, build, and ship experiences that make a real difference. We believe great design can make hard things possible, even delightful.

We are building an AI-native design organization — and we mean that seriously. We're looking for designers who are already working this way: using AI to prototype ideas quickly, shorten customer feedback loops, and ship quality UX directly to customers. This isn't a future aspiration — it's how we work now, and it's changing what the design role looks like at Gusto and across the industry.

About the team

Contractors play a huge role in our economy, and are becoming more prevalent every year. Contract work offers flexibility and independence for workers, and hiring contractors helps small business owners scale quickly and access specialized skills. Our Contractors team helps small and medium business owners (SMBs) hire, manage, and pay domestic and international contractors. We also help contractors manage their client engagements and build their own thriving businesses.

About the role

As a staff product designer, you’ll help bring our contractor products to maturity. You’ll be the IC design leader across this area, driving foundational shifts to our platform and customer experiences. This is a unique opportunity to make major experience changes to established, business critical workflows. As part of the cross-functional leadership team, you’ll drive the entire product development process from setting the long-term vision to strategic planning; all the way to launching new features and iterating on existing ones.

Here’s what you’ll do day-to-day

Drive end-to-end design strategy and execution across the contractors experience from discovery and visioning through iterative delivery and refinement.
Partner with product, engineering, research, data, legal, compliance, operations, and support to define problem spaces, align on priorities, and deliver solutions that meet both customer and business needs.
Translate insights from research and data into intuitive, scalable experiences that support a variety of customer workflows.
Champion thoughtful, inclusive design by participating in design reviews, sharing feedback, and contributing to design standards and platform quality.
Bring genuine AI fluency to your design practice, using it to prototype quickly, shorten feedback loops, and improve contractor experiences.
Mentor and support fellow designers by offering thoughtful critique, sharing knowledge, and contributing to design community initiatives across Gusto.

Here’s what we're looking for:

8+ years of product design experience with demonstrated impact in complex domains.
Proven ability to lead design direction at the product level and influence cross-functional partners.
Strong collaboration experience with partners in product, engineering, research, and data.
A portfolio that demonstrates high-quality interaction and visual design with thoughtful consideration for accessibility and end-to-end user experiences.
Comfort translating ambiguity into clear design decisions and outcomes.
Strong communication skills with the ability to align teams around shared goals.
Demonstrated AI fluency in your design practice. You're using AI to move faster, prototype more, and get to better decisions.

Compensation Details

At Gusto, we strive to provide rewards that empower employees to achieve their financial and personal goals. We offer competitive compensation packages with a strong emphasis on equity based compensation (ownership in Gusto). To learn more about Gusto’s compensation philosophy and benefits offerings please view our Total Rewards Approach page.

Our cash compensation range for this role is $146,000/yr to $183,000/yr in Denver & most remote locations, and $177,000/yr to $222,000/yr in San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

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