Enter a job title or keyword

Senior Staff Service Designer

Gusto


Job Location:

Chicago, IL - USA

Monthly Salary: Not provided by the employer
Posted: 4 June 2026 (30+ days ago)
Application Deadline: 1 September 2026
Vacancies: 1 Vacancy
The job posting is outdated and position may be filled

Job Summary

About Gusto

At Gusto were 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 500000 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. Learn more about our Total Rewards philosophy.


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 the Role:

A customer running payroll doesnt experience the product CX and AI as separate things. They experience one service made up of many teams systems and handoffs working together. When those handoffs are well designed the experience holds up. When they arent when its unclear who owns an escalation what happens when the AI gets something wrong or how an exception moves between systems and teams the customer absorbs the cost.

As AI becomes a larger part of the customer experience the design challenge changes. More of the experience now depends on how work moves between AI systems product experiences and human teams. This role focuses on making those interactions more coherent resilient and understandable both for customers and for the teams operating the service behind the scenes.

Youll join a team thats already operating with strong executive support and an active body of work across onboarding escalation design journey measurement and AI-enabled service delivery. This is the second IC hire on a foundational team growing from two to three during a major shift toward AI-enabled service experiences.

What makes this role different from many service design roles is that youll be building with AI not just designing around it. The team is prototyping AI-assisted workflows that help product and operational teams think through servicing implications earlier in the development process so that questions like what happens if this breaks and where does the customer go next get addressed during planning not discovered later through operational failure.

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. Were a cross-functional group that is always looking for opportunities to build understanding and empathy for the people who use Gusto. We dont 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. Were 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 isnt a future aspiration its how we work now and its changing what the design role looks like at Gusto and across the industry.

Heres what youll do day-to-day:

  • Complex customer journeys where coordination matters most. Cross-cutting journeys where outcomes depend on coordination across people systems operations and AI and where breakdowns are costly. The work includes understanding how these journeys operate today shaping the intended service experience identifying the operational capabilities needed to deliver it sustainably improving how work routes between teams and systems and establishing how journey health is measured over time.
  • AI-assisted service design workflows. Building tools and workflows that help product and operational teams think through service implications before launch: What happens if something fails How does escalation work Where does the customer go next How will teams know whether the experience is performing well
  • Distributed practice enablement. Helping adjacent practitioners including product designers product operations managers and process improvement analysts apply service design methods in their own domains through reusable tools guidance training and support.
  • Cross-journey coordination and learning. Helping teams work from shared patterns and operating assumptions so customers experience Gusto as a coordinated service rather than disconnected systems. This includes identifying recurring failure patterns shaping reusable approaches and improving how the organization learns from service performance over time.

Heres what were looking for:

  • Credible inside a product cadence. You shape decisions from within delivery pressure not by running parallel workshops or alignment programs. You understand how product organizations make decisions and can operate inside that rhythm.
  • Influence without authority. You help stakeholders see consequences and tradeoffs by creating clarity not by pitching or evangelizing. Youre comfortable when leaders decide differently than youd recommend. You respect decision rights.
  • Makes the complex legible. You take a messy multi-team service system and create representations that teams can reason about together. The artifact is a tool for shared understanding not a deliverable to hand off.
  • Works with operational reality. Youve spent meaningful time with frontline and operational teams and use that input to inform strategy. You understand that customer experience is an outcome of how business systems interact product business rules frontline teams back office ops external constraints.
  • Designs for the service implications of AI. You think through what happens when the AI gets it wrong how uncertainty should be represented to customers how work routes between automated and human support and how to preserve customer agency. You treat AI not just as a workflow tool but as a delivery component that changes how the service behaves.
  • Judgment under ambiguity. You move work forward when the data is incomplete ownership is unclear and the problem spans multiple domains.
  • Designs for operational sustainability.You understand that good services dont sustain themselves. Beyond shaping the experience itself you think about the organizational capabilities stewardship models and learning mechanisms needed to help teams deliver and evolve the service successfully over time.
  • Strong communicator. You communicate vision concepts and recommendations clearly to a variety of audiences including leadership creating alignment and motivating action without jargon

Experience:

  • 8 years of service design experience including meaningful work inside technology organizations alongside product engineering CX and operational teams.
  • Experience helping teams make decisions and move work forward inside fast-moving product and operational environments.
  • Demonstrated ability to make complex service ecosystems understandable through maps models frameworks or other working representations that stakeholders can navigate discuss and build on together.
  • Track record of influencing roadmap operational or investment decisions through strong judgment clear framing and thoughtful articulation of tradeoffs and implications.
  • Experience designing or operating services where AI automation or algorithmic systems shaped how work was delivered including how those systems interacted with human teams and customer-facing experiences. Candidates without direct AI experience should demonstrate strong judgment about how technology changes service delivery and organizational behavior.
  • Experience working directly with frontline and back-office operational teams and incorporating operational realities into service and experience design work.
  • Understanding of how services are sustained over time through organizational capabilities such as training workflows ownership models support structures measurement and continuous improvement.
  • Adjacent experience in research analytics systems design operations or human-in-the-loop services is valuable.
  • Experience operating inside complex scaled technology organizations is strongly preferred.

AI Fluency:

AI fluency is core to this role. We expect candidates to enter at the Integrator level on Gustos AI Fluency Framework meaning AI is a regular integrated part of how they work rather than an occasional experiment.

For service design specifically this includes using AI to synthesize cross-functional inputs explore failure modes model service behaviors and think through operational implications such as routing escalation ownership and exception handling. At this level AI fluency also includes helping others work more effectively by sharing methods building reusable workflows and contributing to team capability.

The strongest candidates are building reusable tools frameworks prompts workflows or approaches that others can adopt independently. We also value discernment: the ability to evaluate AI-generated outputs critically recognize when analysis is incomplete or misleading and apply strong judgment rather than accepting outputs at face value.

Experience with tools such as Claude Claude Code or similar agentic workflows is helpful along with comfort prototyping AI-assisted workflows and using prompt-based approaches for structured analysis. Candidates are not expected to be engineers but should be comfortable building and experimenting with AI-enabled ways of working.

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 Gustos compensation philosophy and benefits offerings please view our Total Rewards Approach page.

Our cash compensation range for this role is $173000/yr to $215000/yr in Denver & most remote locations and $203000/yr to $253000/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.

#LI-DNI

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 Gustos 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 its 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. Gusto considers qualified applicants with criminal histories consistent with applicable federal state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject toGustos Applicant Privacy Notice.


Required Experience:

Staff IC


About Company

Company Logo

Unlock maximum tax savings with minimal effort. Gusto tax specialists help you claim eligible expenses and get the credit your business deserves.

View Profile View Profile