B2B Field Sales - Outside Sales

System One, Inc.; Pittsfield (MA); On-site; USD 60,000 - 110,000; Full time

Job summary

System One, Inc. is seeking a driven B2B Field Sales professional for the Outside Sales role focused on Merchant Services. You will manage a Massachusetts territory, conduct on-site product demos, and close deals with SMBs through both referrals and self-sourced opportunities.

The role emphasizes quota attainment, relationship building, and end-to-end sales execution. You will collaborate with partner banks and business bankers to expand the pipeline, while owning the full sales cycle from

Qualifications

• Experience in field sales, preferably B2B.
• Ability to manage a defined territory and generate referrals.

Responsibilities

• Sell Clover POS to SMBs in assigned territory.
• Conduct on-site demos and presentations at client sites.
• Own full sales cycle from prospecting to closing.
• Build and maintain relationships with business bankers and partners.
• Meet or exceed quota and KPI targets.

Skills

Outside sales

Territory mgmt

Prospecting

Relationship building

Job description

Permanent, full-time, direct-hire W2 role [ base annual salary + uncapped commissions + residuals ] with full benefits.

B2B Field Sales - Outside Sales ( Merchant Services Business Development )

• Sell Clover, an industry-leading cloud-based point-of-sale (POS) platform used by more than 700,000 merchants and processing over $330 billion in card transactions, to small- and medium-sized businesses (SMBs) in your assigned territory. The platform combines POS hardware and software to handle card, mobile wallet, and contactless payments, alongside business management features such as inventory, reporting, and customer loyalty.
• Manage a territory with dozens of branches from multiple established corporate partner banks, building relationships with business bankers to generate referrals and close deals, while self-sourcing new opportunities to supplement the partner banks’ pipelines.
• Conduct on-site product demos and presentations at client businesses, showing how the platform can streamline operations and boost revenue, and close sales deals in person.
• This is a quota-carrying field sales role focused on driving new business, managing existing relationships, and growing an assigned territory through strong outside sales execution and a self-starter mindset. You'll own the full sales cycle : prospecting, self-sourcing leads, and generating referrals through existing clients and established bank partnerships, and closing deals, with full accountability for territory performance and quota/KPI attainment, including turning around underperforming accounts. Success in this role means building lasting client and partner relationships, identifying challenges early, and consistently delivering proactive solutions that drive growth and retention.
• We're looking for someone with proven outside sales experience who hits quota, works provided leads and builds their own pipeline, closes deals, hunts for new business, connects well with people, and owns their results.