B2B - Outside Sales Executive

About the role

We are seeking a highly motivated, entrepreneurial Outside Sales Representative to drive new business for Simpay by selling our Payment Processing services to local merchants. As an Outside Sales Representative at Simpay, you will generate income through our entire suite of services: Employee Benefits Memberships (Exectras Membership) and Business Insurance.

This is a W-2, commission-only role designed for self-starters who want unlimited earning potential without geographic restrictions. There are no protected or assigned territories — your success is driven by your initiative, activity, and ability to close.

Responsibilities

• Prospect and generate new business through cold calling, networking, referrals, digital outreach, and in-person meetings
• Schedule and conduct sales appointments with business owners and decision-makers
• Deliver compelling, value-driven presentations of our services
• Close new agreements and exceed sales goals
• Develop referral partnerships and centers of influence
• Stay current on product updates and competitive positioning

Compensation Structure

• W-2 employee status
• Large per deal bonuses
• Lifetime Residual Income
• Uncapped earning potential
• Performance bonuses
• Incentives
• Sales training and ongoing support

Requirements

• 2+ years of B2B sales experience preferred
• Experience selling to small or mid-sized businesses strongly preferred
• Background in merchant services/payment processing
• Strong prospecting and closing abilities
• Excellent communication and presentation skills
• Self-motivated with a hunter mentality
• Comfortable operating independently
• Valid driver’s license (if conducting in-person sales)

Ideal Candidate Profile

• Competitive and highly driven
• Comfortable initiating conversations with business owners
• Disciplined in managing your own activity and pipeline
• Resilient and consistent
• Motivated by unlimited earning potential
• Entrepreneurial but value the stability and structure of W-2 employment

Why Join Simpay?

• Sell differentiated payment processing services
• Multiple products and services for cross-sell opportunities
• Build recurring revenue through SMB sales
• Operate without geographic limitations
• Leverage a growing platform designed to support small businesses nationwide