The opportunity
At Gusto, we're 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.
What you'll do
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.
What they're looking for
- 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.
- 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.
