Full Time Conversation Design Jobs (NOW HIRING)

About Gusto
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. With teams in Denver, San Francisco, and New York, we support more than 500,000 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 Design at Gusto
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. We're a cross-functional group that is always looking for opportunities to build understanding and empathy for the people who use Gusto. We don't 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. We're 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 isn't a future aspiration - it's how we work now, and it's changing what the design role looks like at Gusto and across the industry.
About the Role:
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.
About the Team:
The Unified Service Platform team builds the experiences that establish how Gusto customers get help - across self-service, in-product guidance, multi-channel support, and the AI and human experts behind all of it. You'll lead a team of three designers (product and conversation design) within a cross-functional group of engineers, PMs, and data partners, designing for both the small business owners who rely on Gusto and the experts who serve them. Design on USP is a strategic function - embedded in product direction from day one, not brought in at the execution stage.
Here's what you'll do day-to-day:

• 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.

Here's what we're looking for:

• 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.

Compensation Details
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 Gusto's compensation philosophy and benefits offerings please view our Total Rewards Approach page.
Our cash compensation range for this role is $204,000/yr to $238,000/yr in Denver & most remote locations, and $240,000/yr to $280,000/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.
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, Gusto's 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 it's 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.
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