At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff – payroll, health insurance, 401(k)s, and HR – so owners can focus on their craft and their customers.

With teams in Denver, San Francisco, and New York, we support more than 400,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) – because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

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.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic.

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Responsibilities

• Strategic Design Leadership: Create and drive an end-to-end UX strategy for the Ads Platform that aligns with Reddit's mission.
• Product-Led Growth: Lead the design of features that drive self-service adoption, such as in-platform insights, recommendations, and advanced reporting insights.
• Organizational Scaling: Lead and manage a high-performing team of designers, fostering a culture of mentorship and craft excellence.
• Cross-Functional Impact: Partner deeply with Product and Research to drive platform-wide initiatives, ensuring that complex ad technology,such as Ads APIs, billing, and CRM tools,is accessible and user-centric.
• Operational Excellence: Own the quality of the advertiser experience and the efficiency of the design organization by enhancing design systems and high-impact delivery workflows.
• Executive Influence: Effectively communicate and influence at the executive level, serving as a subject matter expert on ad tech industry trends and user behavior.
• Change Management: Exhibit a 'Reddit-first' attitude, showing the ability to quickly pivot design functions to support rapidly changing business priorities and advertiser needs.

Qualifications

• Experience: 10+ years of relevant design experience, with at least 5+ years managing teams of 10+ designers.
• Ad Tech Expertise: Deep functional knowledge of ads management platforms, including Campaign and Creative Management, Reporting/Insights, and Advertiser Growth or similarly complex sales or enterprise systems.
• Visionary Portfolio: A world-class portfolio demonstrating design strategy and systems for complex, professional-grade platforms at scale.
• Strategic Acumen: Proven experience driving company-wide initiatives (like AI-driven automation or business model shifts) with significant business impact.
• Ambiguity Leadership: Ability to build solutions from first principles in ambiguous situations and elevate the performance of the entire Leadership Team.
• User Empathy: A strong sense of empathy for the advertiser journey, balanced with a drive to ship the best possible product.

Benefits:

• Comprehensive Healthcare Benefits and Income Replacement Programs
• 401k with Employer Match
• Global Benefit programs that fit your lifestyle, from workspace to professional development to caregiving support
• Family Planning Support
• Gender-Affirming Care
• Mental Health & Coaching Benefits
• Flexible Vacation & Paid Volunteer Time Off
• Generous Paid Parental Leave

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