Head of PEO Sales, Gusto
$256.7-280k
OTE
+ Restricted Stock Units. This OTE is structured with a target 60% base pay and 40% commission pay with an uncapped commission structure
2-3 days a week in office
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
$256.7-280k
OTE
+ Restricted Stock Units. This OTE is structured with a target 60% base pay and 40% commission pay with an uncapped commission structure
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 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
- PEO Expertise: 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. We're 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 PEO's Jan 1 selling cycle — Sept–Dec 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: Salesforce.com (SFDC) experience required, including pipeline and funnel design; familiarity with HCM platforms and benefits administration tools preferred
What the job involves
- 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 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
- 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
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Co-Founder & Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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