Outside Sales Representative

About Simpay

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 Exectras Membership product.

As an Outside Sales Representative at Simpay, you will also be able to generate income through our entire suite of services: Payment Processing, HR, Business Insurance.

Exectras Membership is a subscription-based benefits platform that helps small and mid-sized businesses offer meaningful healthcare, wellness, insurance, and business support services to their employees — without the high cost and complexity of traditional benefits.

Our mission is simple: empower business owners to better support their employees while strengthening their ability to recruit, retain, and grow.

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. And best of all, you don’t need to be licensed to sell Exectras Membership!

You will prospect, present, and close new membership 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 Exectras Membership
• Identify employer pain points related to healthcare access, employee retention, and benefits gaps
• Close new membership agreements and exceed sales goals
• Build and manage a consistent pipeline in CRM
• 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 on sustained membership
• Uncapped earning potential
• Performance bonuses and 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 payroll, benefits, insurance, HR services, merchant services, or related industries is a plus
• 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

You are:

• 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 a differentiated, high-value membership product
• Build recurring revenue through subscription-based sales
• Operate without geographic limitations
• Leverage a growing platform designed to support small businesses nationwide

If you are ready to create your own opportunity, control your income, and build long-term recurring revenue, we want to hear from you.