Simpay · 4 hours ago
Outside Sales Representative - Payroll
United States
Full-time
Remote
Entry, Mid Level
1+ years expSimpay is dedicated to simplifying the lives of business owners by providing integrated business solutions. The Payroll Sales Representative will focus on generating new business through selling payroll and HR services to small and mid-sized businesses, requiring strong relationship-building and consultative sales skills.
AppsFinancial ServicesMobile PaymentsPayments
Hiring Manager
Matt Wilkerson
Responsibilities
Prospect, qualify, and generate new leads through cold calling, networking, referrals, and in-person visits
Conduct discovery meetings to understand client needs and present tailored payroll and HR solutions
Deliver compelling product demos and presentations to decision-makers
Build and manage a consistent sales pipeline to meet or exceed monthly revenue and account goals
Collaborate with internal teams (implementation, support, underwriting) to ensure a smooth onboarding process for new clients
Maintain accurate records in the CRM, including activity tracking, forecasting, and pipeline management
Represent Simpay professionally at industry events, trade shows, and community networking opportunities
Stay informed on industry trends, competitive offerings, and market opportunities
Provide exceptional service and follow-through to ensure long-term customer satisfaction
Qualification
Required
1–3+ years of experience in B2B sales; payroll/HR sales experience strongly preferred
Proven track record of meeting or exceeding sales targets
Strong consultative selling skills and ability to communicate value effectively
Excellent communication, presentation, and relationship-building skills
Self-motivated, organized, and comfortable working independently in the field
Ability to learn and master Simpay's product suite and technology tools
Valid driver's license and reliable transportation, if applicable
Benefits
Health, dental, and vision insurance.
401(k) with company match.
LTIP (Long Term Incentive Plan)
Eligibility to earn President’s Club trips.
Paid time off and holidays.
Career advancement opportunities in a rapidly expanding organization.
Company
Simpay
Simpay is a fintech company that offers payment solutions for businesses.
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$17MKey Investors
Columbia Pacific Advisors
2021-10-25Debt Financing· $17M
Leadership Team
Lazaros Kalemis
CEO & Co-Founder
John Pfisterer
Chief Financial Officer
Recent News
2026-01-09
2026-01-09
2025-12-09
Company data provided by crunchbase