About Gusto

At Gusto, we're 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 500,000 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 building its PEO sales org from the ground up, and we're looking for a quota-carrying seller to be one of the founding members of that team. This is a true ground-floor opportunity: you'll be among the first reps closing PEO business at Gusto, working directly with the Head of PEO Sales to prove out and scale the motion. You'll drive new PEO revenue by selling Gusto's co-employment solution to both net-new prospects and our existing base of 400,000+ customers — Gusto's single biggest competitive advantage over legacy PEOs. The market opportunity is real, the pace is fast, and the early sellers on this team will help define what "good" looks like.Use AI-powered workflows as a core part of how you sell: running assigned tools daily, surfacing friction and inefficiencies as you find them, and collaborating with your team to influence what gets built or improved next. If you're excited to roll up your sleeves, lead by example, and architect something from scratch, let's talk.

About the Team:

You'll be an early individual contributor on Gusto's founding PEO sales team, reporting to the Head of PEO Sales. As one of the first sellers, you'll carry a personal book of business, run the full sales cycle end to end, and serve as a Subject Matter Expert who guides prospects through complex co-employment buying decisions. You'll partner closely with HR, benefits, and payroll counterparts to deliver a seamless customer experience, and you'll work alongside the Head of PEO to surface what's working in the field — feedback that directly shapes the playbook, tooling, and pipeline architecture as the org scales. 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 to PEO — and you'll be one of the first to run that motion at scale.

Here’s what you’ll do day-to-day:

Own the full sales cycle. Prospect, qualify, run discovery, demo, navigate complex buying groups, and close. This is a quota-carrying role for a seller who's comfortable owning a deal from first touch to signed agreement.
Sell across both motions. Close net-new prospects and convert existing Gusto payroll customers to PEO. You'll learn the distinct objections, value propositions, and rhythms of in-base selling vs. cold-start prospecting.
Serve as a PEO Subject Matter Expert. Guide prospects through co-employment, benefits, compliance, and the practical realities of moving onto a PEO. Build and maintain deep knowledge of PEO compliance, co-employment regulations, and applicable state and federal employment law.
Sell with selling-season fluency. Understand and plan around PEO's concentrated selling window (Sept–Dec, with the bulk of new business landing Jan 1). Build pipeline early and manage your funnel to hit those timelines.
Work the channel. Partner with broker, GA, and accountant referral sources to develop pipeline, and feed insights back on what's converting.
Manage your pipeline rigorously. Keep Salesforce clean and current, forecast accurately, and operate within the sales stages, routing, and reporting the team establishes.
Use AI to sell smarter. Bring genuine AI fluency to your daily workflow — leveraging AI tools for prospecting, call prep, follow-up, and forecast hygiene. We expect our sellers to be hands-on with AI and to share what's working with the broader team.
Collaborate cross-functionally. Work closely with Marketing, Product, and the broader Sales org to surface market signals, sharpen positioning, and improve the customer experience.

Here’s what we're looking for:

PEO / HCM Sales Experience: 4+ years in a closing sales role, ideally in PEO, HCM, or benefits. Direct PEO selling experience is strongly preferred.
Quota Attainment: Consistent, demonstrable track record of meeting and exceeding individual sales targets.
Full-Cycle Ownership: Proven ability to own a deal end to end — prospecting, discovery, multi-stakeholder navigation, and close — in a consultative, complex sale.
Selling-Season Fluency: Familiarity with PEO's Jan 1 selling cycle (Sept–Dec pipeline build, renewal dynamics) is a strong plus and a key screen for PEO-specific experience vs. generic HCM.
Install-Base Conversion: Experience selling into or converting an existing customer base to a higher-tier or adjacent product is a plus.
Channel Familiarity: Understanding of broker, GA, and accountant referral channels in the PEO or benefits space.
Sales Acumen: Strong working knowledge of inbound and outbound sales methodologies in SMB SaaS or HCM/PEO environments.
Collaboration: Ability to work effectively across HR, Benefits, Product, and Marketing; excellent interpersonal skills.
AI Fluency: Proven, day-to-day experience integrating AI into how you work — across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful feedback that helps improve your tools and processes.
Technical Proficiency: Salesforce.com (SFDC) experience required; familiarity with HCM platforms and benefits administration tools preferred.

Our cash compensation amount for this role is $115,000 to $129,500 USD for Denver, Phoenix, Atlanta, Chicago metro areas and $140,000 to $150,000 USD 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, Gusto's 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 it's 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.

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.

PEO Sales, Senior Account Executive