B2B Outside Sales Pro — Uncapped Earnings (Payment Processing)

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

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.