Senior Staff Product Designer, Growth Monetization

About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy. 

About the Role: As a Principal Product Designer for Growth Monetization on the Expansion team, you will lead design efforts that drive revenue growth and product adoption across Gusto’s ecosystem. You’ll define pricing, purchasing, bundling, upsell, and cross-sell experiences, ensuring that customers can easily discover, purchase, and expand their use of Gusto’s offerings.

You’ll work closely with cross-functional partners in Growth, Expansion, Product, Marketing, Engineering, Data Science, and Revenue to create seamless awareness to purchase and adoption flows. This role requires strong systems thinking, expertise in e-commerce and pricing design, and an ability to balance business goals with customer experience.

If you thrive in designing high-impact, growth-focused experiences that enhance acquisition, retention, and expansion, this role is for you.

About the Team: The Growth team at Gusto is dedicated to helping customers find, adopt, and engage with our products meaningfully. Our approach prioritizes a user-centric design ethos, ensuring that growth initiatives are backed by value and trust. As a key contributor, you’ll join a collaborative environment with Engineers, Product Managers, Data Scientists, and strategic Marketing and Business partners, focusing on critical touchpoints in the customer journey.

Here’s what you’ll do day-to-day:

• Design and optimize monetization experiences that improve conversion rates, revenue, and product adoption. This includes pricing pages, checkout flows, bundling, and in-product upsells.
• Develop a unified purchasing experience that enables customers to seamlessly upgrade, expand, or modify their plans across multiple touchpoints.
• Create scalable frameworks for pricing, packaging, and expansion to ensure consistency and usability across all monetization touchpoints.
• Partner with Design Systems teams to establish reusable UI patterns for monetization that integrate seamlessly into Gusto’s product ecosystem.
• Use experimentation and data-driven design to refine monetization flows, leveraging A/B testing, behavioral analytics, and qualitative insights to drive decisions.
• Collaborate with cross-functional teams, including Growth PMs, Revenue, Sales, and Customer Success, to align monetization strategies with business and customer needs.
• Advocate for customer-centric pricing and monetization strategies, ensuring that upsells and expansions enhance—not disrupt—the user experience.
• Shape the long-term vision for monetization design, balancing iterative improvements with a bold, future-state experience for Gusto’s customers.
• Holistic service design: Design with marketing, sales, and customer support needs in mind so you can deliver a cohesive and logical flow from first contact to activation.
• Commitment to craft: Maintain a high standard of excellence in UX, systems-thinking, service design, and content design, ensuring all solutions are both functional and elegant.

Here’s what we're looking for:

• 10+ years of experience in full-stack product design, with expertise in growth, monetization, e-commerce, and pricing strategy.
• Proven track record of designing and optimizing monetization flows such as pricing, checkout, cross-sells, and upsells for B2B SaaS or consumer platforms.
• Strong understanding of growth principles, behavioral psychology, and customer decision-making.
• Experience working on multi-product ecosystems, ensuring seamless upgrade and expansion experiences.
• Ability to lead complex projects, balancing business needs with customer-centric design principles.
• Expertise in A/B testing, behavioral analytics, and research-driven experimentation.
• Proficiency in content design, crafting clear, concise, and actionable in-product copy to support user success.
• Strong collaboration and communication skills,