Principal PM, AI Assistant for Small Business

Jobtailor; California (MO); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Gusto seeks a senior product manager to own the product vision for its conversational assistant, building AI-enabled experiences for small businesses.

You will collaborate with engineering, data, design and UX research to expand coverage across payroll, time, benefits, and compliance while shaping third-party and first-party integrations.

Join a hands-on, cross-functional team focused on delivering fast value through iterative, narrow product slices and clear leadership guidance.

Qualifications

• 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.
• Belief in and enthusiasm for building AI for small businesses.
• Experience building trusted AI products, including writing evals and forming a point of view on AI quality.
• Hands-on builder who prefers building over delegating.
• Comfortable spanning platform thinking and UX/experience judgment.
• Knowledge of RAG, ontology, and scalable API strategy for agent-accessible systems.
• Comfortable with a fluid, expanding charter.
• Active engagement with AI tools relevant to the role and willingness to grow AI fluency.

Responsibilities

• 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 priorities across third-party connectors, messaging channels, AI clients, and first-party app surfaces.
• Partner with engineering and data teams on API, MCP, model, platform, 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 customer value early.
• Drive decisions with Gusto leadership and product leaders across the company.

Skills

Product Management

AI Product Development

API Strategy

UX Judgment

Leadership Engagement

Tools

AI Tools

MCP

UX Research

Messaging Channels

Conversational Interfaces

Third-Party Integration

Data Analysis

Platform Thinking

Job description

Gusto seeks a senior product manager to own the product vision for its conversational assistant, building AI-enabled experiences for small businesses.

You will collaborate with engineering, data, design and UX research to expand coverage across payroll, time, benefits, and compliance while shaping third-party and first-party integrations.

Join a hands-on, cross-functional team focused on delivering fast value through iterative, narrow product slices and clear leadership guidance.