B2B Outside Sales Executive

Simpay; Boston (MA); On-site; USD 50,000 - 100,000; Full time

Benefits offered by this job

Lifetime Residual Income

Performance bonuses

Sales training and ongoing support

Job summary

Simpay is seeking a highly motivated Outside Sales Representative to drive new business in payment processing. This commission-only role offers unlimited earning potential without geographic restrictions.

Ideal candidates have 2+ years of B2B sales experience and strong closing abilities. You will grow your income by generating new agreements with small and mid-sized businesses, supported by unlimited training and sales resources.

Qualifications

• 2+ years of B2B sales experience preferred.
• Experience selling to small or mid-sized businesses strongly preferred.
• Strong prospecting and closing abilities.

Responsibilities

• Prospect and generate new business through various methods.
• Schedule and conduct sales appointments with business owners.
• Deliver value-driven presentations of services.
• Close new agreements and exceed sales goals.
• Develop referral partnerships and stay current on product updates.

Skills

B2B sales experience

Prospecting ability

Closing skills

Communication skills

Independent operation

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.

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.

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 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 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

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 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

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