Remote
Financial
jobscollider
About this role
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.
Abo
Commission Structure
Base Salary
$,k
Commission
Structure not specified
Ramp Period
Not mentioned — clarify timeline
Selling Motion
Prospecting
Outbound-Heavy
Self-sourced pipeline via cold outreach
Buyer Persona
Director-Level
Mid-senior decision-makers
Territory
Greenfield
Build territory from scratch — net-new logos
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
Ownership stake offered
Financial Services — Interview Intel
Typical Sales Cycle
3–6 months (Retail) · 6–18 months (Institutional)
Common Buyer Objections
- "Regulatory concerns — need compliance approval"
- "We already have a vendor for this"
- "Need to see 3-year track record"
- "Committee-based decision — multiple approvers"
Key Industry Metrics
Hot Topics to Reference
- • AI in fraud detection and compliance
- • Open banking APIs
- • ESG investing mandate shifts
- • Embedded finance partnerships
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionAs an Account Executive with Gusto, you'll own the entire revenue pipeline and be measured on quota attainment.
Trust-building is paramount — prospects need confidence in your expertise.
Remote positions in sales offer flexibility but require strong self-discipline and proactive communication with distributed teams.
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