Head of Design, Unified Service Platform

Gusto, Inc.•Quinte West, ON

13d•$204,000 - $280,000•Hybrid

About The Position

Gusto's Unified Service Platform (USP) is the infrastructure behind how small businesses get help when it matters most — AI-driven support, multi-channel service, and the human expertise that steps in when AI isn't enough. We're looking for a Head of Design to lead the design team behind it and set the bar for what AI-native service design looks like at Gusto. This is a people-leadership role. You'll lead, coach, and grow a small, high-caliber team of three designers — spanning product design and conversation design — and you'll be accountable for the quality, direction, and delivery of design across the platform. You'll also be the design voice on the USP quartet, peer-to-peer with PM, Engineering, and Data leaders — authoring strategy in ambiguous spaces and spearheading cross-functional convergence. And it's a genuine player-coach role: alongside leading the team, you'll stay hands-on on the highest-leverage design work yourself. If you want to build and lead the team defining AI-native service design — at the exact moment the category is being invented — this is that role.

Requirements

Experience managing and growing product designers — you've led a team, developed designers, run performance and growth, and built a healthy team culture. Managing across disciplines (e.g., content/conversation design alongside product design) is a well-developed plus.
Design leadership in ambiguity — you set direction and a high craft bar, co-own strategy with cross-functional peers, and hold a position when the right answer is unpopular.
AI-product judgment in consequential domains — you've shipped (or led teams that shipped) AI-mediated experiences in production, and can speak to uncertainty, errors, graceful failure, and human override.
Service design depth — real journey mapping and blueprinting on two-sided products with operational handoffs, not workshop exercises.
Hands-on AI fluency — you use AI-native tools yourself and can raise your team's fluency; you perceive AI as part of the craft, not separate from it.
12+ years of design experience, including 5+ years managing designers, with clear ownership of shipped work in a B2B SaaS environment.

Responsibilities

Lead, coach, and grow a team of three designers (product + conversation design) — own their development, careers, performance, and craft growth, and create the conditions for them to do their best work.
Own design direction and quality across USP — set the vision and the bar, and be accountable for the team's outcomes, not just its output.
Stay hands-on where it matters most — as a player-coach, prototype and design the hardest flows and quartet-level artifacts yourself, not just review them; flex your hands-on time down as the team grows.
Represent design on the USP quartet — co-lead product direction with PM, Engineering, and Data leaders; author strategy and POV in ambiguous spaces; drive convergence and close decisions.
Set the standard for AI-native service design. This includes how trust, uncertainty, graceful failure, and AI-human handoffs show up on the platform. You will identify when AI outputs are ready to ship, when a human is needed, and when outputs should not be sent out at all.
Guide service design end-to-end — journey mapping, blueprinting, and operational handoffs for a two-sided product — through your team.
Champion an AI-native design practice — model and expect fluency with AI-native tools (Claude Code, Cursor, and comparable agentic tools) as part of the craft, and raise the floor for how the team designs.
Partner on hiring and team building as the team grows.