Principal Product Manager, AI Assistant

Gusto

. Develop a deep understanding of small-business workflows inside Gusto .

Posted 9/23/2026full-timeUnited StatesLead💰 $179,000 - $260,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in product management with a focus on building trusted AI products, driving product vision, and making platform-level decisions. Proficient in collaborating with cross-functional teams to enhance user experience and expand product capabilities.

Highest-signal resume keywords

Product ManagementAI Product DevelopmentAPI StrategyUser Experience JudgmentCross-Functional Collaboration

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Product VisionProduct StrategyAI Quality AssessmentAPI DevelopmentPlatform ThinkingWorkflow UnderstandingTechnical Trade-offsNarrow Product ShippingScalable API StrategyConversational Assistant Development

Soft Skills

Leadership EngagementCustomer Value DeliveryAdaptabilityCommunication

Tools & Technologies

AI ToolsThird-Party ConnectorsMessaging Channels

Industry Keywords

Small-Business WorkflowsPayrollTime ManagementBenefitsCompliance

About the role

Key responsibilities & impact

Develop a deep understanding of small-business workflows inside Gusto
Lead the product vision and strategy for Gusto’s conversational assistant
Expand assistant tool and domain coverage across payroll, time, benefits, and compliance
Define the assistant’s ecosystem surfaces, including third-party connectors, messaging channels, and AI clients
Partner with engineering and data teams on API, MCP layer, first-party surface, and technical trade-offs
Partner with design and UXR to understand customer attitudes toward AI acting on their behalf
Ship narrow product slices quickly to deliver early customer value
Drive product and platform-level decisions in a high-visibility role

Requirements

What you’ll need

10+ years building as a product manager
Experience owning meaningful scope and driving broad product or platform-level decisions
Comfortable engaging directly with Gusto leadership and product leaders across the company
Understanding of building trusted AI products, including writing evals and assessing AI quality
Hands-on builder who prefers building over delegating
Comfortable spanning platform thinking and UX/experience judgment
Sharp perspectives on RAG, ontology, and scalable API strategy for agent-accessible systems
Comfortable with a fluid, expanding charter
Ability to actively engage with AI tools relevant to the role and grow AI fluency
Secure, reliable, and consistent internet connection when working outside a Gusto office

Benefits

Comp & perks

Competitive base pay
Health insurance
401(k)
Equity (RSUs)
Hybrid work arrangement
Equal opportunity employer
Reasonable accommodations for qualified individuals with disabilities and disabled veterans