Greenhouse ·
full-timePrincipal Product Manager, AI Assistant
Gusto · Denver, CO - Hybrid; New York, NY - Hybrid; San Francisco, CA - Hybrid
Gusto provides a platform for small businesses to manage payroll, benefits, and HR operations. As a Principal Product Manager for the AI Assistant, you will lead the vision and strategy for the company's conversational AI tools. This role involves deep collaboration with cross-functional teams to identify manual workflows that can be automated, enabling small business owners to manage complex tasks like payroll and benefits with greater efficiency. You will be responsible for defining the behavior and capabilities of the AI assistant, ensuring it provides reliable, high-value support while maintaining the trust required for financial and HR-related decision-making. The position requires a candidate who is comfortable working in an ambiguous, fast-paced environment and possesses a strong technical understanding of AI models, API design, and product architecture. You will be expected to act as a hands-on builder, prototyping solutions and integrating AI directly into the core user experience to solve real-world problems for small business customers. This role is well-suited for an experienced product leader who is eager to drive AI-native product development and thrives in a lean, outcome-oriented team structure.
Education
- Batch: 2024
- Level: Bachelor's degree
- Courses: B.E
Key Skills
Notes
0-1 year experience eligible.
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. By the Numbers: Named #1 best software for small business of 2024 by G2 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing Over $500M in annual revenue The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs There are 6.2M employers in the US, 98% have fewer than 100 employees (1) 550,000 new businesses are created each year in the US (1) What Product Management is like at Gusto: Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools automating what slows teams down and amplifying what makes them creative and high-performing. We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care. We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence. We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto. About the CoreX AI team: CoreX AI builds and powers AI experiences that make Gusto the best teammate for small businesses. Our largest AI bets embed directly in small business workflows whether that's answering a quick question or handling the task itself. Our customers trust us with their payroll, their employees' benefits, and their money decisions where mistakes have real, immediate consequences. We give small businesses trusted and powerful AI tools that supercharge how they work. We're at an inflection point across everything we own, and we're looking for a product leader ready to accelerate our AI bets as we build toward that future. This is a role for builders who can work across Gusto, reason about API design and model behavior as comfortably as customer experience, and bring hands-on experience building with AI. About the Role: You'll define how Gusto's conversational assistant works, behaves, and earns customer trust and how small businesses use it to get real work done across payroll, benefits, HR, and beyond. Develop a deep understanding of how small businesses actually work inside Gusto today the workflows they run, where they get stuck, and the work they'd hand off if they could Lead the product vision for Gusto’s conversational assistant that gives small businesses superpowers, and turn it into a coherent strategy a sharp perspective on where the assistant earns real value, and what we build first Expand what the assistant can actually do. You'll partner with domain teams to grow tool and domain coverage across payroll, time, benefits, and compliance, and hold the bar on quality as coverage grows measured in real actions customers complete, not conversations they have Define how we show up in our customers’ ecosystem and the surfaces where work naturally happens third-party connectors, messaging channels, and AI clients and decide what earns priority against the depth we have in the app Partner with engineering and data teams on technical trade-offs: how we expose Gusto's capabilities to agents through our API and MCP layer, how the assistant embeds into our first-party surfaces, and where we take on debt to move faster Partner with design and UXR to understand how customers actually feel about AI acting on their behalf, and use that to shape how we build Move fast. Speed is our top priority, and you'll set a pace that reflects it shipping narrow slices that get customers value early rather than waiting on the complete build Here’s what we're lo
Skills for this role
Required skills
Also mentioned in the listing
| Role | Principal Product Manager, AI Assistant |
|---|---|
| Company | Gusto |
| Location | Denver, CO - Hybrid; New York, NY - Hybrid; San Francisco, CA - Hybrid |
| Compensation | Not disclosed |
| Posted | 2026-09-29 |
| Deadline | Rolling |
Typical process for this type of role
A general guide — the exact steps for this specific listing may vary; check the original posting for details.
- 1ApplicationSubmit your resume through the apply link.
- 2ScreeningRecruiter reviews your background against the role.
- 3AssessmentA technical test, assignment, or coding round, depending on the role.
- 4Interview(s)One or more rounds with the hiring team.
- 5OfferOffer letter with compensation and start date.
Before you apply
0/4Principal Product Manager, AI Assistant at Gusto: frequently asked questions
- Who can apply for the Principal Product Manager, AI Assistant role at Gusto?
- The listing asks for Bachelor's degree (B.E); graduating batches 2024; freshers are welcome.
- What skills does the Principal Product Manager, AI Assistant role require?
- The listing highlights AI. Show each of these in a project or past role on your resume.
- What is the salary for this role?
- Gusto has not stated compensation in the listing. Check the original posting or ask during the application process.
- Is the Principal Product Manager, AI Assistant position remote, hybrid or onsite?
- The listing marks this role as hybrid, with Denver, CO - Hybrid; New York, NY - Hybrid; San Francisco, CA - Hybrid as the location.
- What is the application deadline?
- Gusto has not listed a fixed deadline, so apply early in case the opening is filled.
- How do I apply for the Principal Product Manager, AI Assistant role?
- Use the Apply button on this page. It opens the original listing on job-boards.greenhouse.io, where you submit your application with the company.
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