Demo

Outside Sales Rep - Mid Market Chicago

SalesFirst Recruiting-1
Chicago, IL Full Time
POSTED ON 5/21/2026
AVAILABLE BEFORE 6/19/2026

THE COMPANY

Our client is a national leader in payroll, HR technology, human capital management, and workforce solutions for small and mid-sized businesses. The company provides software and services that help employers manage payroll, HR, compliance, benefits, onboarding, and workforce administration.

This is an opportunity for an experienced HCM sales professional to join a recognized market leader with strong brand equity, a competitive compensation plan, and a field-based new-business sales environment.


THE JOB

The Mid-Market Consultant is responsible for selling HCM and payroll software solutions to businesses with 1–99 employees. This is a full-prospecting role with no assigned referral sources, requiring strong outbound activity, field sales execution, and territory management.

The successful candidate will identify target accounts, prospect new business, conduct consultative sales meetings, manage pipeline activity, and close new clients.

RESPONSIBILITIES

  • Prospect and generate new business opportunities
  • Sell payroll and HCM solutions to SMB and mid-market businesses
  • Manage full sales cycle from prospecting through close
  • Conduct in-person and virtual sales meetings
  • Build and manage territory pipeline
  • Maintain accurate forecasting and CRM activity
  • Compete effectively against other HCM providers
  • Develop consultative relationships with business decision-makers
  • Execute outbound prospecting strategies
  • Achieve monthly and annual quota expectations


THE QUALIFICATIONS

Must-Have Requirements

  • 2–10 years of B2B sales experience
  • Direct HCM experience required
  • Proven quota attainment
  • Prospecting and full-cycle sales experience
  • Valid driver’s license and reliable transportation
  • Comfortable with field-based sales activity

Preferred Qualifications

  • Payroll, HRIS, PEO, or workforce management experience
  • Experience selling to SMB or mid-market organizations
  • Salesforce CRM experience
  • Strong consultative sales ability
  • Stable tenure and strong career progression


THE BENEFITS

  • $70K base salary
  • $60K variable compensation
  • $130K OTE at 100% quota
  • Approx. $500/month vehicle and cell reimbursement after training
  • Hybrid work structure
  • Strong onboarding and sales training
  • Career growth opportunities
  • Comprehensive healthcare benefits
  • 401(k) with employer contribution
  • PTO and company holidays

Salary : $60,000 - $70,000

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