Outside Sales Executive - B2B

Simpay; Illinois; Remote; USD 90,000 - 150,000; Full time

Benefits offered by this job

Lifetime residual income

Uncapped earning potential

Performance bonuses

Ongoing sales training

Job summary

Simpay is seeking an ambitious Outside Sales Representative to drive new business for our payment processing services to local SMBs. You will also help customers with our broader suite, including employee benefits and business insurance opportunities.

This W-2, commission-only role offers lifetime residual income and uncapped earning potential, with performance bonuses and ongoing support to help you succeed across any market you pursue.

Qualifications

• 2+ years of B2B sales experience preferred.
• Experience selling to small/mid-sized businesses is strongly preferred.
• Background in merchant services or payment processing is beneficial.

Responsibilities

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

Skills

B2B sales

Prospecting & closing

Merchant services

Self-motivated hunter

Job description

Do you want to earn lifetime residual income AND work for a company you can trust? Welcome to Simpay. Our goal is to simplify the lives of business owners by providing our customers with solutions that save them time and money.

Position Overview

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 don’t have to just sell payment processing. You will also be able to generate income through our entire suite of services: Employee Benefits Memberships (Exectras Membership), Business Insurance.

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.

You will prospect, present, and close new payment processing agreements with small and mid-sized employers across any market you choose to pursue.

What You’ll Do

• 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
• Lifetime Residual Income
• Uncapped earning potential
• Performance bonuses
• Incentives Sales training and ongoing support

This role is ideal for professionals who prefer performance-based income with unlimited upside.

Qualifications

• 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