Job Overview
Location
Denver, CO;Las Vegas, NV;Atlanta, GA;Chicago, IL;Phoenix, AZ;Toronto, Ontario, CAN - Remote
Job Type
Full-time
Category
Sales
Date Posted
April 14, 2026
Full Job Description
đź“‹ Description
- • Head of PEO Sales at Gusto, Inc. is a founding leadership role responsible for designing and launching Gusto’s Professional Employer Organization (PEO) sales organization from the ground up, leveraging the company’s existing base of 400,000+ small business customers as a key growth engine.
- • Day-to-day responsibilities include carrying a personal book of business while building the team and infrastructure, defining sales stages and pipeline architecture in Salesforce, owning the full talent lifecycle (hiring, onboarding, coaching), developing channel strategies with brokers and accountants, converting existing payroll customers to PEO, planning around the seasonal PEO selling cycle (Sept–Dec), collaborating cross-functionally with Sales, Marketing, and Product, using data to drive decisions, leading AI adoption across the team, and cultivating a culture of excellence with deep PEO compliance knowledge.
- • The role sits within Gusto’s sales organization and reports to sales leadership, working closely with HR, benefits, payroll, and product teams to deliver a seamless customer experience and shape PEO product strategy. Gusto supports over 400,000 small businesses nationwide with payroll, health insurance, 401(k)s, and HR solutions, and is committed to building a workplace that reflects the people it serves.
- • In this role, you will have the opportunity to architect a new sales motion from scratch, establish scalable processes and infrastructure, directly impact revenue growth through new and existing customer conversion, develop leadership and team-building expertise in a high-growth SaaS environment, gain deep fluency in PEO compliance and co-employment solutions, and become a recognized leader in AI-enabled sales practices while advancing your career at a mission-driven company focused on small business success.
🎯 Requirements
- • 5+ years of experience in PEO sales, with direct experience standing up a PEO sales org or building a sales team 0→1 in a high-growth environment
- • Proven player-coach ability to carry personal quota while simultaneously building team, process, and infrastructure
- • Experience developing or executing strategies to convert an existing customer base to a higher-tier or adjacent product, with familiarity in in-base PEO conversion motions
- • 5+ years of people management in a sales organization, including direct involvement in recruiting and hiring
- • Salesforce.com (SFDC) experience required, including pipeline and funnel design; familiarity with HCM platforms and benefits administration tools preferred
🏖️ Benefits
- • Competitive base pay, benefits, and equity (RSUs) as part of Gusto’s Total Rewards philosophy
- • Opportunity to work remotely from Denver, CO; Las Vegas, NV; Atlanta, GA; Chicago, IL; Phoenix, AZ; or Toronto, Ontario, CAN
- • Hybrid office model with expected in-office presence 2–3 days per week at physical locations in Denver, San Francisco, or New York City
- • Commitment to AI fluency and adoption, with support for leveraging AI tools to enhance sales effectiveness and team performance
- • Access to professional development, career pathing, and a culture of excellence focused on skill growth and long-term impact
Skills & Technologies
About Gusto, Inc.
Gusto is a cloud-based payroll, benefits, and human resources platform for small and midsize U.S. businesses. It automates payroll processing, tax filing, workers' compensation, health insurance, 401(k), time tracking, and employee onboarding while ensuring compliance with federal, state, and local regulations. Founded in 2011, the company serves over 300,000 customers and integrates with accounting, banking, and productivity applications to streamline back-office operations.
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