Chris Cosgrove

Chris Cosgrove leads product at Gusto as Chief Product Officer and Head of Small Business Platform, overseeing tools for small businesses. He previously led Square’s invoices and bill-pay business as a general manager and worked on data products at Quotient Technology.

Career

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PatientNow

Sep 2026 — Present

Advisor

Gusto

Aug 2025 — Present

Chief Product Officer & Head of Small Business Platform

Square

Jan 2023 — Mar 2024

General Manager

Quotient Technology

Jan 2014 — Apr 2016

Group Product Manager — Data Products

Accenture

Jun 2006 — Dec 2013

Manager

Products & media

gusto.com

Bringing business context and action into Claude

Chris explains how Gusto’s connector uses payroll, people and time data to prepare business tasks, with owners reviewing actions before they take effect.

gusto.com

Gusto Fall Showcase 2026: Helping Small Business Owners Start, Run, and Grow

An overview of new Gusto products and features for business formation, compliance, payroll, and automation.

Writing

gusto.com

More Ways to Run Payroll and Stay Ahead of Compliance, Now in the Gusto Plugin for ChatGPT

How the Gusto ChatGPT plugin can help prepare payroll, address compliance tasks, and automate small-business administration.

Writing

gusto.com

Gusto App Now Available in ChatGPT: A New Era of AI for Small Businesses

An introduction to using Gusto data in ChatGPT to answer payroll questions, analyze trends, and run payroll for select customers.

Writing

gusto.com

Gusto Now Works Where You Do: Introducing Gusto in Claude and Slack

How eligible customers can access Gusto data and run payroll from Claude and Slack.

Writing

gusto.com

Introducing Scheduling in Gusto: Plan and Manage Your Team’s Time in One Place

A look at Gusto’s scheduling feature, including coordinating shifts with time tracking, time off, and payroll.

Writing

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Chris Cosgrove

PatientNow

Gusto

Square

Quotient Technology

Accenture

Products & media

Bringing business context and action into Claude

Gusto Fall Showcase 2026: Helping Small Business Owners Start, Run, and Grow

More Ways to Run Payroll and Stay Ahead of Compliance, Now in the Gusto Plugin for ChatGPT

Gusto App Now Available in ChatGPT: A New Era of AI for Small Businesses

Gusto Now Works Where You Do: Introducing Gusto in Claude and Slack

Introducing Scheduling in Gusto: Plan and Manage Your Team’s Time in One Place

Curated Lists

List Inclusions