Head of PEO Sales
Gusto, Denver, CO, United States
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 0→1 opportunity to establish Gusto's PEO sales org from the ground up, and we're looking for someone who is energized by that challenge.
You will drive new PEO revenue by selling Gusto's co‑employment solution to both prospects and our existing base of 400,000+ customers — Gusto's single biggest competitive advantage over legacy PEOs. The pace is fast, the market opportunity is real, and we're 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 you're excited to roll up your sleeves, lead by example, and architect something from scratch, let's talk.
About The Team You will be the founding leader of Gusto's PEO sales function. In the first 6–12 months, you'll operate as a true player‑coach – personally closing deals while simultaneously building the team, tooling, and infrastructure around you. You'll 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: Gusto's existing install base. Like the best scaled PEOs, a meaningful share of your pipeline will come from converting existing payroll customers – and you'll be the one to design and build that on‑ramp.
Here’s What You’ll Do Day‑to‑day
Carry a personal book of business while building the team and infrastructure around you.
Design the sales motion from scratch, defining sales stages, lead routing, funnel metrics, and pipeline architecture in Salesforce.
Own the full talent lifecycle, partnering closely with Recruiting to define hiring profiles and onboard new hires.
Build and leverage the channel ecosystem, developing a point of view on broker, GA, and accountant referral channels.
Convert the install base, developing the playbook for converting Gusto's existing 500K+ payroll customers to PEO.
Operate with selling season fluency, planning around PEO’s concentrated selling window (Sept–Dec, with ~50–60% of new business landing Jan 1).
Collaborate cross‑functionally with Sales, Marketing, and Product leadership to identify market opportunities and help shape PEO product strategy.
Use data to drive decisions, tracking, measuring, and reporting on sales effectiveness.
Lead with AI fluency, modeling and driving AI adoption across your team.
Build a culture of excellence, guiding career pathing and deepening knowledge of PEO compliance, co‑employment regulations, and related laws.
Here’s What We're Looking For
PEO Expertise – 5+ years in PEO sales, with direct experience standing up a PEO sales org or building a sales team 0→1. Prioritize builder profiles.
Player‑Coach Experience – proven ability to carry personal quota while building team, process, and infrastructure.
Selling Season Fluency – experience operating within PEO’s Jan 1 selling cycle.
Install Base Conversion – experience developing or executing strategies to convert an existing customer base.
Channel Strategy – understanding of broker, GA, and accountant referral channels in PEO or benefits space.
RevOps & Pipeline Architecture – experience building or contributing to Salesforce pipeline design.
Management Experience – 5+ years of people management in a sales organization, including 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.
Collaboration – ability to work effectively across Sales, HR, Benefits, and Product teams.
AI Leadership – demonstrated ability to evaluate, adopt, and champion AI and automation tools.
Technical Proficiency – Salesforce.com experience required; familiarity with HCM platforms and benefits admin tools preferred.
Compensation
– Our target on‑target earnings (OTE) for this role is $256,667/yr to $280,000/yr in Denver & most remote locations, and $292,133/yr to $318,000/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.
Office expectations
– Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees 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, Gusto's subsidiary, whose physical office is in Scottsdale. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.
Gusto values diversity and 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. 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.
Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
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You will drive new PEO revenue by selling Gusto's co‑employment solution to both prospects and our existing base of 400,000+ customers — Gusto's single biggest competitive advantage over legacy PEOs. The pace is fast, the market opportunity is real, and we're 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 you're excited to roll up your sleeves, lead by example, and architect something from scratch, let's talk.
About The Team You will be the founding leader of Gusto's PEO sales function. In the first 6–12 months, you'll operate as a true player‑coach – personally closing deals while simultaneously building the team, tooling, and infrastructure around you. You'll 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: Gusto's existing install base. Like the best scaled PEOs, a meaningful share of your pipeline will come from converting existing payroll customers – and you'll be the one to design and build that on‑ramp.
Here’s What You’ll Do Day‑to‑day
Carry a personal book of business while building the team and infrastructure around you.
Design the sales motion from scratch, defining sales stages, lead routing, funnel metrics, and pipeline architecture in Salesforce.
Own the full talent lifecycle, partnering closely with Recruiting to define hiring profiles and onboard new hires.
Build and leverage the channel ecosystem, developing a point of view on broker, GA, and accountant referral channels.
Convert the install base, developing the playbook for converting Gusto's existing 500K+ payroll customers to PEO.
Operate with selling season fluency, planning around PEO’s concentrated selling window (Sept–Dec, with ~50–60% of new business landing Jan 1).
Collaborate cross‑functionally with Sales, Marketing, and Product leadership to identify market opportunities and help shape PEO product strategy.
Use data to drive decisions, tracking, measuring, and reporting on sales effectiveness.
Lead with AI fluency, modeling and driving AI adoption across your team.
Build a culture of excellence, guiding career pathing and deepening knowledge of PEO compliance, co‑employment regulations, and related laws.
Here’s What We're Looking For
PEO Expertise – 5+ years in PEO sales, with direct experience standing up a PEO sales org or building a sales team 0→1. Prioritize builder profiles.
Player‑Coach Experience – proven ability to carry personal quota while building team, process, and infrastructure.
Selling Season Fluency – experience operating within PEO’s Jan 1 selling cycle.
Install Base Conversion – experience developing or executing strategies to convert an existing customer base.
Channel Strategy – understanding of broker, GA, and accountant referral channels in PEO or benefits space.
RevOps & Pipeline Architecture – experience building or contributing to Salesforce pipeline design.
Management Experience – 5+ years of people management in a sales organization, including 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.
Collaboration – ability to work effectively across Sales, HR, Benefits, and Product teams.
AI Leadership – demonstrated ability to evaluate, adopt, and champion AI and automation tools.
Technical Proficiency – Salesforce.com experience required; familiarity with HCM platforms and benefits admin tools preferred.
Compensation
– Our target on‑target earnings (OTE) for this role is $256,667/yr to $280,000/yr in Denver & most remote locations, and $292,133/yr to $318,000/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.
Office expectations
– Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees 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, Gusto's subsidiary, whose physical office is in Scottsdale. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.
Gusto values diversity and 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. 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.
Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
#J-18808-Ljbffr