PEO Sales, Senior Account Executive

Gusto•Chicago, NY

13h•Hybrid

About The Position

Gusto is building its PEO sales organization from the ground up and is seeking a quota-carrying seller to be a founding member of the team. This is a ground-floor opportunity to 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. The role involves driving new PEO revenue by selling Gusto's co-employment solution to both net-new prospects and the existing base of over 400,000 customers. The position requires using AI-powered workflows as a core part of selling, running assigned tools daily, identifying inefficiencies, and collaborating with the team to influence product development. This role is for individuals excited to roll up their sleeves, lead by example, and architect something from scratch.

Requirements

4+ years in a closing sales role, ideally in PEO, HCM, or benefits.
Direct PEO selling experience is strongly preferred.
Consistent, demonstrable track record of meeting and exceeding individual sales targets.
Proven ability to own a deal end to end — prospecting, discovery, multi-stakeholder navigation, and close — in a consultative, complex sale.
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.
Experience selling into or converting an existing customer base to a higher-tier or adjacent product is a plus.
Understanding of broker, GA, and accountant referral channels in the PEO or benefits space.
Strong working knowledge of inbound and outbound sales methodologies in SMB SaaS or HCM/PEO environments.
Ability to work effectively across HR, Benefits, Product, and Marketing; excellent interpersonal skills.
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.
Salesforce.com (SFDC) experience required; familiarity with HCM platforms and benefits administration tools preferred.

Nice To Haves

Direct PEO selling experience
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.
Familiarity with HCM platforms and benefits administration tools preferred.

Responsibilities

Own the full sales cycle: Prospect, qualify, run discovery, demo, navigate complex buying groups, and close.
Sell across both motions: Close net-new prospects and convert existing Gusto payroll customers to PEO.
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. 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.