Senior Staff Service Designer

Gusto, Inc.•Toronto, ON

10d•$173,000 - $253,000•Hybrid

About The Position

This role focuses on making customer interactions more coherent, resilient, and understandable, especially as AI becomes a larger part of the customer experience. The Senior Staff Service Designer will work on a foundational team that is prototyping AI-assisted workflows to help product and operational teams consider servicing implications earlier in the development process. The goal is to address questions like “what happens if this breaks?” and “where does the customer go next?” during planning, rather than discovering them later through operational failure. The designer will be building with AI, not just designing around it, and will contribute to an AI-native design organization that uses AI for rapid prototyping, shortening feedback loops, and shipping quality UX.

Requirements

Credible inside a product cadence, shaping decisions within delivery pressure.
Ability to influence without authority by creating clarity on consequences and tradeoffs.
Skill in making complex service ecosystems understandable through representations that stakeholders can use for shared understanding.
Experience working with frontline and operational teams, incorporating their input into strategy.
Understanding of how customer experience is an outcome of interacting business systems (product, business rules, frontline teams, back office ops, external constraints).
Ability to design for the service implications of AI, including AI failure modes, uncertainty representation, routing between automated and human support, and preserving customer agency.
Judgment under ambiguity, moving work forward with incomplete data and unclear ownership across multiple domains.
Ability to design for operational sustainability, considering organizational capabilities, stewardship models, and learning mechanisms.
Strong communication skills to convey vision, concepts, and recommendations clearly to various audiences, including leadership.
8+ years of service design experience, including meaningful work within technology organizations alongside product, engineering, CX, and operational teams.
Experience helping teams make decisions and move work forward in fast-moving product and operational environments.
Demonstrated ability to make complex service ecosystems understandable through maps, models, frameworks, or other working representations.
Track record of influencing roadmap, operational, or investment decisions.
Experience designing or operating services where AI, automation, or algorithmic systems shaped delivery, including interactions with human teams and customer-facing experiences.
Experience working directly with frontline and back-office operational teams and incorporating operational realities into design work.
Understanding of how services are sustained over time through organizational capabilities (training, workflows, ownership models, support structures, measurement, continuous improvement).
AI fluency at the Integrator level, meaning AI is a regular, integrated part of how they work.
Ability to use AI for synthesizing inputs, exploring failure modes, modeling service behaviors, and considering operational implications.
Ability to critically evaluate AI-generated outputs and apply strong judgment.
Comfort 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.
Experience operating inside complex scaled technology organizations.
Experience with tools such as Claude, Claude Code, or similar agentic workflows.
Comfort prototyping AI-assisted workflows and using prompt-based approaches for structured analysis.
Ability to build reusable tools, frameworks, prompts, workflows, or approaches that others can adopt independently.

Responsibilities

Design complex customer journeys where coordination across people, systems, operations, and AI is critical.
Understand current journey operations, shape the intended service experience, and identify necessary operational capabilities for sustainable delivery.
Improve work routing between teams and systems and establish methods for measuring journey health.
Build tools and workflows to help product and operational teams consider service implications before launch, including failure modes, escalation processes, and customer next steps.
Enable adjacent practitioners (product designers, product operations managers, process improvement analysts) to apply service design methods through reusable tools, guidance, training, and support.
Foster cross-journey coordination and learning by helping teams work from shared patterns and operating assumptions.
Identify recurring failure patterns, shape reusable approaches, and improve organizational learning from service performance.