Senior Staff Service Designer

Gusto•Chicago, NY

9d•Hybrid

About The Position

A customer running payroll doesn’t 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 aren’t — when it’s 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. You’ll join a team that’s 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 you’ll 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.

Requirements

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. You're comfortable when leaders decide differently than you'd 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. You've 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 don’t 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
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.
AI fluency is core to this role. We expect candidates to enter at the Integrator level on Gusto’s 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.

Nice To Haves

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.

Responsibilities

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.