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. Read more about Design at Gusto.

About the Role:

We’re looking for a product designer to join our Time Tools team, a key area of growth for Gusto. As a core design contributor in this product area, you’ll partner closely with PM, Engineering, and Data peers to shape high-priority initiatives. You’ll be responsible for designing experiences that help small business owners and their employees manage time with confidence and ease.

This role offers the opportunity to own major product initiatives end-to-end—from uncovering customer needs to shipping polished, performant, and accessible experiences. You’ll collaborate with other designers on the team, contribute to our design system, and help elevate the craft quality of our product.

Time Tools is also at the forefront of how AI shows up in Gusto's products. Scheduling automation, compliance flagging, and PTO recommendations are all areas where AI outputs will increasingly inform real decisions for small business owners and hourly workers—and where getting it wrong has direct consequences. We're looking for a designer who brings a clear, considered point of view on how to design these experiences: when to surface AI, when to require human judgment, and how to communicate uncertainty in ways people can actually act on.

About the Team:

Time and Attendance is our flagship in a suite of add-ons designed to complement Gusto Payroll. The add-on helps small business owners track time, create and share schedules, manage attendance, and seamlessly sync hours to payroll—all within the Gusto platform. The team’s scope includes:

• Time tracking: Allow employees to log hours via web, app, or kiosk, supporting flexible work arrangements like remote and flextime.
• Scheduling: Create and manage employee schedules, accommodating shifts, availability, and shift swaps.
• Time off policies and requests: Automate time off management, support complex PTO policies, and ensure compliance with labor laws.
• PTO balances: Keep track of employee time off with automatic updates that sync vacation and sick days with payroll and calendars.
• Project tracking: Manage projects with tools for tracking time spent on tasks, analyzing progress, and adjusting workloads.

Here’s what you’ll do day-to-day:

• Define the experience framework for how small business owners and hourly workers interact with time data, including where automation should handle decisions, where humans need to stay in control, and how to surface errors without creating compliance risk.
• Design for AI within the product itself—ideally including scheduling recommendations, PTO automation, and compliance alerts—establishing clear patterns for surfacing AI outputs, keeping humans in control of high-stakes decisions, and communicating errors in ways that protect workers and employers alike.
• Design and refine multi-surface experiences (web, mobile, kiosk) that meet the needs of both managers and employees.
• Partner with PM, Engineering, and Data to define problem spaces, set priorities, and deliver customer value.
• Champion our design system and evolve it through contributions that improve platform cohesion.
• Balance long-term vision with near-term execution, navigating ambiguity and adjusting scope as customer needs evolve.
• Provide thoughtful critique and mentorship to peers, helping elevate craft quality across the team.

Here’s what we're looking for:

• You have 8+ years of product design experience, with a portfolio demonstrating accessible, performant, and thoughtful end-to-end design across web and mobile.
• You design with AI as a core material—prototyping recommendations, defining human override patterns, and handling failure modes responsibly. You set clear criteria for when AI-generated outputs should be trusted, surfaced, or overridden, and partner cross-functionally to establish principles for fairness, transparency, and control.
• You partner with PM and Engineering to shape priorities, translate them into clear roadmaps, and drive clarity through complex, ambiguous problem spaces.
• You uncover and synthesize customer needs—particularly for small businesses and hourly workers—into actionable design insights that inform product direction.
• You've designed complex systems or compliance-heavy workflows—ideally in SaaS, HR, or productivity tools—and can balance early-stage adoption with long-term system design.
• You scale quality through reusable patterns, thoughtful critique, and a passion for helping small businesses and their employees thrive.

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.

About the Role:

We’re hiring a Staff Product Designer for our Benefits team to design and launch a new product offering at Gusto. Our focus in Benefits is simple: help small businesses and their employees get access to better quality care at more affordable rates—in other words, we make benefits work harder for small businesses.

Benefits is a notoriously complex space, full of confusing choices, high stakes, and fragmented experiences across employers, employees, carriers, and brokers. In this role, you’ll partner closely with Product Managers, Engineers, Data Science, CX, Operations, and Sales to turn that complexity into experiences that feel clear, human, and trustworthy—from end-to-end journeys to the underlying systems that power them.

This is an opportunity to shape a new part of Gusto’s Benefits offering and deliver meaningful, tangible impact for small businesses and the people who rely on them.

About the Team:

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.

Here’s what you’ll do day-to-day:

• Lead 0→1 discovery and design for a new Benefits product offering—from problem framing to MVP definition—grounded in real employer + employee workflows.
• Design end-to-end service experiences across employer, employee, and internal ops workflows—identifying where AI can reduce complexity while keeping decisions clear and controllable.
• Design AI-assisted decision moments that help customers choose and act with confidence. 
• Design the system that makes AI safe and scalable: define objects, rules, states, and exception paths plus guardrails for when AI should defer to humans.
• Make data legible and operational: shape the information model and UX so humans and AI can collaborate—clean inputs, clear outputs, and structured handoffs that reduce errors and rework.
• Build product feedback loops that improve AI quality over time: define success metrics, evaluation signals, and human-in-the-loop review patterns to continuously tune guidance, routing, and automation.
• Design in code to ship faster: use AI-assisted dev tools (e.g., Cursor, Claude Code) to prototype and deliver production-quality UI, collaborating tightly with engineering and shaping reusable patterns.

Here’s what we're looking for:

• You partner cross-functionally to define human-in-the-loop workflows, and set principles for fairness, privacy, and trust. 
• You design with AI as a core material—prototyping, refining prompts, and integrating AI behaviors that adapt responsibly to user context. You guide teams in balancing automation with transparency and control. 
• You redesign service blueprints where AI plays an active role—automating routine workflows, predicting needs, and escalating complex cases to humans with transparency and context.
• You define area strategy using measurable bets and experimentation; partner with Analytics and AI teams to track and evaluate impact.
• You scale quality through reusable patterns, thoughtful critique, and mentorship; balance exploration with delivery.
• You influence cross-functional strategy across teams; resolve complex trade-offs and guide design through ambiguity.
• You coach across teams, build onboarding and training programs, and raise the bar for craft and systems thinking.

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.

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.

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 role:

We’re hiring a Principal Product Designer to lead AI design across Gusto.

This is one of the most senior individual contributor design roles at the company. You’ll define how AI works, behaves, and earns trust across the Gusto platform – starting with Gus, our AI conversational assistant, and expanding into AI-powered workflows embedded in payroll, benefits, HR, and beyond. You’ll shape the interaction model, UX principles, and product direction for AI across Gusto. You will work with senior Product and Engineering leaders to define our AI portfolio. You will develop important AI features that customers will consider and you’ll ship high-impact, customer-facing AI capabilities that help our customers get their work done faster and more effectively, while building their trust in Gusto. These features will help customers finish their tasks faster and build their trust in Gusto.

This role is both strategic and hands-on. We’re looking for someone who can set a long-term UX vision for AI and turn it into real, shipped product that meaningfully improves how small businesses get work done.

Here’s what you’ll do day-to-day:

• Define and evolve the UX vision for our Gus conversational assistant and AI experiences across the Gusto platform.
• Lead and ship Tier 1 AI initiatives from early concept through launch and iteration.
• Design full AI-powered workflows – shaping how users provide input, how model outputs are validated and acted on, and how the experience handles risk, uncertainty, and failure.
• Partner closely with AI Product and Engineering leaders to translate complex technical constraints into intuitive, credible user experiences.
• Establish scalable AI interaction patterns and design principles that teams across Gusto can adopt.
• Write and iterate on prompts in collaboration with engineering, PM, and content design.
• Use AI tooling to accelerate exploration and prototyping, customer feedback loops, and shipping to customers.
• Mentor designers on the AI team and coach designers across Gusto who are shipping AI features.
• Advocate for high-quality, responsible AI experiences across Design and R&D.

Here’s what we're looking for:

• Proven AI product impact: You’ve shipped LLM-driven product experiences to production and can demonstrate measurable impact on adoption, efficiency, or user trust.
• Systems-level thinking: You’ve designed complete AI workflows – not just chat interfaces – and can speak fluently about failure modes, guardrails, user control, and transparency.
• Strategic product influence: You’ve defined UX direction at a portfolio or company level and influenced roadmap, scope, and sequencing decisions in partnership with senior PM and Engineering leaders.
• Technical fluency: You’re comfortable collaborating with highly technical AI engineers. You understand concepts like retrieval, context management, latency, and model reliability, and can translate them into robust UX decisions.
• Builder mindset: You ship. You prototype. You iterate. You’re not interested in defining principles without turning them into real customer impact.
• Organizational leadership: You have enhanced team work quality. You achieved this by coaching team members, setting new standards, and building solid partnerships across different functions.

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 $204,000/yr to $238,000/yr in Denver & most remote locations, and $240,000/yr to $280,000/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.

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:

The Retirement team at Gusto builds financial products and services that help bridge the retirement gap for small business owners and their employees. With 401(k) plans designed to be affordable, easy to manage, and easy to understand, Gusto is working to make retirement accessible to small businesses and teams that have historically been underserved by the 401(k) market.

We’re a collaborative group that values creativity, transparency, and a deep respect for our craft. We hold ourselves to a high bar and actively support one another so that we can do our best work. Our process incorporates using AI in our daily workflows to move faster, explore ideas, and increase our impact. From building tools that help individuals navigate their financial future to new retirement offerings, the Retirement team plays a central role in contributing to Gusto’s mission. 

About the Role:

We’re hiring a Staff Product Designer to partner with Product, Engineering, Data (and Research) to shape strategy, align partner teams, and create a cohesive, high-trust retirement experience across the employer and employee journey. You’ll operate as the design lead for your projects—co-owning priorities, success metrics and driving alignment across Retirement and key partner teams (Payroll, Benefits, Support/Ops). Your scope will include:

• Improving both setup and account management to boost confidence, adoption, and retention to reduce contact rate and confusion.
• Creating a more connected journey between payroll and retirement by designing across the seams of product, operations, and support—where the hardest and most interesting problems live.
• Designing flexible, scalable patterns across Retirement, integrating seamlessly with adjacent payroll and benefits touchpoints. Apply discerning design judgment to determine when and how to effectively incorporate AI to enhance the experience.

If you’re energized by ambiguous problem spaces, high-trust financial experiences, and designing workflows that make complex decisions feel clear and confident—this role is for you.

Here’s what you’ll do day-to-day:

• Strategic Vision & Partnership: Partner with Product Management to define the customer problems to solve, the strategy to solve them, and the measurable outcomes that matter—across activation, engagement, and retention.
• Data and research informed iteration: Collaborate with Data and Research to understand funnel drop-offs, behavior over time, retention drivers as well as define success metrics and iterate based on what you learn.
• Design Leadership & Ownership: Drive the full design process for shipped experiences—scoping and sequencing work, prototyping, testing, and delivering MVP → iteration → longer-term improvements.
• Trust + compliance design: Translate regulatory/tax-driven requirements into clear flows, content, and UI patterns that build trust without overwhelming customers.
• Communication & Storytelling: Craft compelling product narratives that align cross-functional stakeholders around the problem, strategic options, and tradeoffs, clearly explaining the reasoning behind design decisions and outcomes.
• Elevating Craft & Mentorship: Provide thoughtful critique and mentorship to design peers; raise the quality bar across the organization. Be an innovation driver with using and designing for AI.
• System Advocacy & Evolution: Champion the design system and contribute patterns/components that improve cohesion and quality.
• AI-Accelerated Prototyping & Learning: Use AI to move quickly from concept to customer-tested artifact — building clickable, high-fidelity prototypes that generate real signal faster than traditional methods allow. Bring a clear point of view on where AI enhances the customer experience, not just your workflow, and help raise the team's fluency through your example.

Here’s what we're looking for:

We’ve found that a low ego, a growth mindset, and a bias for action go a long way here. 

• 8+ years in product design, with a portfolio showing end-to-end shipped work and the impact it drove
• High bar for craft across interaction design, information architecture, and visual design—especially for complex, form-heavy workflows
• Bonus: Experience in regulated/high-trust domains (fintech, taxes, insurance, healthcare, benefits/retirement)
• Demonstrable AI fluency in your design practice — not just familiarity with tools, but evidence of AI changing how you prototype, test, and ship. We'll ask you to show this, not just describe it.
• Comfort moving between design and code — whether that means shipping UI improvements directly, working closely in the codebase with engineers, or using AI-assisted tools to close the gap between prototype and production.
• Comfortable operating in ambiguity and shaping messy inputs into clear goals, tradeoffs, and shipped outcomes
• Bonus: Comfortable tackling content design aspects (making complex concepts understandable)
• Building strong partnerships with Product, Engineering, and Data to prioritize, execute, and iterate
• Systems thinker who designs solutions that scale beyond one-off screens and hold up across a product ecosystem
• Bonus: Have contributed to growing a Design system with components or patterns
• Bring a clear point of view, engage in constructive feedback, and help teams align quickly by clarifying tradeoffs and driving decisions forward
• Track record leading multi-workstream initiatives across teams—setting direction, unblocking partners, and shipping measurable improvements

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.

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.

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 $172,000/yr to $215,000/yr in Denver & most remote locations, and $202,000/yr to $253,000/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.