Account Executive

Overview

You sell Justworks' HR, payroll, and benefits platform to small business owners—think restaurants, retail, small tech companies, and professional services firms with 5-200 employees. You're competing against Gusto, Rippling, TriNet, and the status quo of them doing payroll through their accountant or QuickBooks. Most of your deals are self-sourced through cold calling and email, though you'll get some inbound leads from their marketing.

Role Snapshot

Company Context

Stage: Late-stage private / near-public (1500+ employees, well-funded)

Size: 1533 employees

Growth: Hiring AEs across 10+ major metros suggests geographic expansion strategy

Market Position: Established player in crowded PEO/HRIS space—recognized brand but facing intense competition from Gusto, Rippling, and legacy players

GTM Reality

Pipeline Sources:

• 30% Inbound - web form fills, free trial sign-ups, content downloads. Quality varies widely; many are tire-kickers or businesses too small to be viable
• 60% Outbound - cold calling into business owner lists, LinkedIn prospecting, attending local business events
• 10% Referrals/Partners - existing customers, broker relationships, accountant referrals

SDR/AE Structure: Mostly self-sourcing. Some metro markets have SDR support, but don't count on it. You're expected to generate most of your own pipeline.

SE Support: No dedicated SEs. You run your own demos. Implementation team handles post-sale, but you need to know the product well enough to demo benefits enrollment, payroll setup, and compliance features.

Competitive Landscape

Main Competitors:

• Gusto (similar market, cheaper, strong brand with startups)
• Rippling (more expensive, broader HR suite, appeals to tech companies)
• TriNet, Insperity (traditional PEOs, older buyers)
• Status quo (accountant does payroll, spreadsheets for HR)

How They Differentiate: Justworks positions as simpler than enterprise PEOs but more full-service than Gusto. Their PEO model means better benefits rates for small companies. Compliance and local tax handling is a key selling point.

Common Objections:

• "We're happy with Gusto/our current setup"
• "Too expensive compared to doing it ourselves"
• "We're too small" or "We'll look at this next year"
• "Our accountant handles payroll"
• Switching friction—migration feels like work they don't have time for

Win Themes: Benefits cost savings, compliance peace of mind, time savings for the owner, better employee experience during onboarding

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (35%) | Internal/Admin (25%)

Key Activities

• Cold calling business owners: You're making 40-60 calls per day to hit activity metrics. Most go to voicemail. You're trying to book 8-12 discovery calls per week. Business owners are busy and hard to reach.
• Running demos: 30-45 minute screen shares walking through payroll setup, benefits enrollment, and compliance features. You're doing 5-8 demos per week. Many prospects no-show or reschedule last minute.
• Chasing deals through the pipeline: Following up with prospects who said "let me think about it" or "check back next quarter." A lot of your pipeline sits stagnant waiting for open enrollment, a new hire trigger, or budget approval.
• Coordinating implementation: Once a deal closes, you hand off to the implementation team but stay involved for the first payroll run to make sure it goes smoothly. This takes 2-3 hours per new customer.

The Honest Reality

What's Hard

• Small business owners are nearly impossible to reach by phone. You'll leave dozens of voicemails that never get returned.
• Long lag time between "interested" and "ready to buy." Deals sit in your pipeline for quarters because they're waiting for open enrollment or their current contract to expire.
• Price sensitivity—these are small businesses watching every dollar. You'll lose deals over $50/month differences.
• Switching friction is real. Even when they like your product better, the work of migrating payroll and benefits data feels daunting.
• You're competing against inertia as much as competitors. "Good enough" is your biggest enemy.

What Success Looks Like

• Closing 4-6 new customers per month (mix of small $8K deals and larger $30K+ deals)
• Maintaining 20+ active opportunities with clear next steps
• Hitting 100+ prospecting activities per week (calls, emails, LinkedIn touches)
• 15-20% demo-to-close rate

Who You're Selling To

Primary Buyers:

• Small business owners (CEO/Founder of 10-100 person companies)
• Office managers or HR generalists (at slightly larger 50-200 person companies)
• CFOs at high-growth startups who've outgrown Gusto

What They Care About:

• Cost—what's this going to cost per employee per month, all-in?
• Ease of migration—how much work is this going to be to switch?
• Benefits quality—can they offer better health insurance rates than they get now?
• Compliance confidence—will this handle multi-state payroll tax correctly?
• Time savings—will this actually reduce the hours they spend on payroll and HR admin?

Requirements

• 2-4 years of B2B sales experience (SMB sales experience preferred)
• Comfortable with high-volume prospecting and self-sourcing pipeline
• Ability to have business-level conversations with owners about costs, benefits, and compliance
• CRM hygiene and activity discipline (they'll track your calls, emails, meetings closely)
• Located in or willing to relocate to one of the listed metros (this is not remote)
• Comfortable running your own demos without SE support