[Remote] Head of PEO Sales

Note: The job is a remote job and is open to candidates in USA. Gusto is on a mission to grow the small business economy by providing essential services like payroll and HR. They are seeking a builder-minded sales leader to establish their PEO sales organization from the ground up, driving new revenue and converting existing customers.

Responsibilities

• Sell and build simultaneously. For the first 6–12 months, carry a personal book of business while building the team and infrastructure around you. This is a player-coach role that requires someone comfortable operating at both levels
• Design the sales motion from scratch. Define sales stages, lead routing, funnel metrics, and pipeline architecture in Salesforce. This org doesn't have a pre-built RevOps foundation — you'll build it
• Own the full talent lifecycle. Partner closely with Recruiting to define hiring profiles, run interviews, and select top PEO sales talent. Onboard new hires for fast ramp and continuously assess team capacity to stay ahead of headcount needs
• Build and leverage the channel ecosystem. Develop a point of view on broker, GA, and accountant referral channels. Even if you don't own these relationships day one, you'll be expected to shape the strategy and lay the groundwork for a scalable partner channel
• Convert the install base. Develop the playbook for converting Gusto's existing 500K+ payroll customers to PEO. Understand the unique motion, objections, and value proposition for in-base selling vs. cold-start prospecting
• Operate with selling season fluency. Understand and plan around PEO's concentrated selling window (Sept–Dec, with ~50–60% of new business landing Jan 1). Build team capacity, pipeline targets, and go-to-market rhythms accordingly
• Collaborate cross-functionally with Sales, Marketing, and Product leadership to identify market opportunities, drive pipeline, and help shape PEO product strategy
• Use data to drive decisions — from advisor skill development to team-level initiatives. Track, measure, and report on sales effectiveness; adjust programs as needed
• Lead with AI fluency. As a people leader at Gusto, you're expected to actively model and drive AI adoption across your team — not just as a user, but as a champion. This means leveraging AI tools to surface pipeline insights, accelerate coaching, improve forecast accuracy, and identify at-risk deals earlier. You'll help your team integrate AI into daily workflows (outreach, call prep, follow-up), experiment with new tooling, and share learnings across the broader sales org. We expect our leaders to stay ahead of the curve and bring a point of view on how AI can make the team meaningfully better
• Build a culture of excellence. Cultivate each individual's skill set and guide career pathing as they grow within the organization. Ensure the team maintains deep knowledge of PEO compliance, co-employment regulations, and applicable state and federal employment law requirements

Skills

• 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 ability to carry personal quota while simultaneously building team, process, and infrastructure
• Direct experience operating within PEO's Jan 1 selling cycle — Sept–Dec pipeline build, renewal dynamics, and capacity planning
• Experience developing or executing strategies to convert an existing customer base to a higher-tier or adjacent product
• Understanding of broker, GA, and accountant referral channels in the PEO or benefits space
• Experience building or significantly contributing to Salesforce pipeline design — sales stages, lead routing, funnel reporting
• 5+ years of people management in a sales organization, including direct involvement in recruiting and hiring
• Consistent track record of establishing and exceeding measurable goals
• Strong working knowledge of inbound and outbound sales methodologies in SMB SaaS or HCM/PEO environments
• Ability to work effectively across Sales, HR, Benefits, and Product teams; excellent interpersonal skills
• Demonstrated ability to evaluate, adopt, and champion AI and automation tools in a sales environment
• Salesforce.com (SFDC) experience required, including pipeline and funnel design
• Familiarity with HCM platforms and benefits administration tools

Benefits

• All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success.
• Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role).
• When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.

Company Overview

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