Head of PEO Sales

About Gusto

At Gusto were on a mission to grow the small business economy. We handle the hard stuff payroll health insurance 401(k)s and HR so owners can focus on their craft and their customers. With teams in Denver San Francisco and New York we support more than 400000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay benefits and equity (RSUs) because everyone who helps build Gusto should share in its success. Offer amounts are determined by role level and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

About the Role:

Gusto is searching for a builder. Not a manager of an existing PEO sales team a founder-minded sales leader who will design the motion write the playbook hire the team and carry a personal book of business in the early months. This is a 01 opportunity to establish Gustos PEO sales org from the ground up and were looking for someone who is energized by that challenge.

You will drive new PEO revenue by selling Gustos co-employment solution to both prospects and our existing base of 400000 customers Gustos single biggest competitive advantage over legacy PEOs. The pace is fast the market opportunity is real and were looking for someone who will bring experience creativity and a genuine passion for building to the table every single day. You align with our company values and have a knack for building for the long haul. If youre excited to roll up your sleeves lead by example and architect something from scratch lets talk.

About the Team:

You will be the founding leader of Gustos PEO sales the first 612 months youll operate as a true player-coach personally closing deals while simultaneously building the team tooling and infrastructure around you. Youll define the ideal customer profile build out the sales stages and pipeline architecture in Salesforce and establish the channel strategy (including broker and accountant referral partnerships) that will drive scalable new business over time.

This team will serve as Subject Matter Experts on PEO guiding prospects through complex buying decisions and partnering closely with HR benefits and payroll counterparts to deliver a seamless customer experience. Your biggest unfair advantage: Gustos existing install base. Like the best scaled PEOs a meaningful share of your pipeline will come from converting existing payroll customers and youll be the one to design and build that on-ramp.

Heres what youll do day-to-day:

• Sell and build simultaneously. For the first 612 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 doesnt have a pre-built RevOps foundation youll 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 dont own these relationships day one youll be expected to shape the strategy and lay the groundwork for a scalable partner channel.
• Convert the install base. Develop the playbook for converting Gustos 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 PEOs concentrated selling window (SeptDec with 5060% 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 youre 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. Youll 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 individuals 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.

Heres what were looking for:

• PEO Expertise: 5 years of experience in PEO sales with direct experience standing up a PEO sales org or building a sales team 01 in a high-growth environment. Were prioritizing builder profiles over tenure in a mature org.
• Player-Coach Experience: Proven ability to carry personal quota while simultaneously building team process and infrastructure. This is not a pure management role in the early stages.
• Selling Season Fluency: Direct experience operating within PEOs Jan 1 selling cycle SeptDec pipeline build renewal dynamics and capacity planning. This is a key screen for PEO-specific operating experience vs. generic HCM.
• Install Base Conversion: Experience developing or executing strategies to convert an existing customer base to a higher-tier or adjacent product. Familiarity with in-base PEO conversion motions is a strong plus.
• Channel Strategy: Understanding of broker GA and accountant referral channels in the PEO or benefits space. Ability to develop a POV and lay groundwork for scalable partner-sourced pipeline.
• RevOps & Pipeline Architecture: Experience building or significantly contributing to Salesforce pipeline design sales stages lead routing funnel reporting from an early-stage starting point.
• Management Experience: 5 years of people management in a sales organization including direct involvement in recruiting and hiring.
• Results-Oriented: Consistent track record of establishing and exceeding measurable goals.
• Sales Acumen: Strong working knowledge of inbound and outbound sales methodologies in SMB SaaS or HCM/PEO environments.
• Collaboration: Ability to work effectively across Sales HR Benefits and Product teams; excellent interpersonal skills.
• AI Leadership: Demonstrated ability to evaluate adopt and champion AI and automation tools in a sales environment. Comfortable going beyond personal usage setting expectations building habits and holding the team accountable to AI-enabled ways of working.
• Technical Proficiency: (SFDC) experience required including pipeline and funnel design; familiarity with HCM platforms and benefits administration tools preferred.

Our target on-target earnings (OTE) compensation for this role is $256667/yr to $280000/yr in Denver & most remote locations and $292133/yr to $318000/yr for San Francisco & New York. This OTE is structured with a target 60% base pay and 40% commission pay with an uncapped commission structure. Final offer amounts and the exact base/commission split are determined by multiple factors including candidate location experience and expertise and may vary from the amounts listed above.

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). The same office expectations apply to all Symmetry roles Gustos subsidiary whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office a secure reliable and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because its the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race color religion national origin age sex (including pregnancy childbirth or related medical conditions) marital status ancestry physical or mental disability genetic information veteran status gender identity or expression sexual orientation or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories consistent with applicable federal state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey please fill out this form and a member of our team will get in touch with you.

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