Principal Product Manager, AI Assistant

Jobtailor

California (MO)

Hybrid

USD 120,000 - 180,000

Full time

6 days ago

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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

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

Requirements

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

Core Competencies

Demonstrates expertise in product management with a focus on AI solutions for small businesses, emphasizing hands-on building, strategic decision-making, and collaboration with cross-functional teams. Proficient in developing product vision and driving initiatives that enhance user experience and operational efficiency.

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