B2B - Outside Sales Executive

Simpay; Boston (MA); On-site; USD 70,000 - 120,000; Full time

Benefits offered by this job

Lifetime residual income

Uncapped earnings

Performance bonuses

Sales training & ongoing support

Job summary

Simpay is seeking an energetic Outside Sales Representative to drive new business for our payment processing services with local merchants. This role offers W-2 status with commission-based earnings and uncapped upside, plus opportunities to cross-sell our broader services to SMBs nationwide.

The ideal candidate will prospect, present, and close agreements, build relationships with business owners, and thrive in a performance-driven environment with ongoing training and support.

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).

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.

Skills

B2B sales

Merchant services

Prospecting

Closing

Communication

Self-motivated

Independent work

Driver's license

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
• 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

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