Goodwin Recruiting

Director of Sales

Chicago, Illinois 22 hours ago
Full-time Sales

Job Description

We are seeking a high-performing, results-driven fintech sales hunter to drive net-new revenue within the payments and retail technology space. Join a high-performing team where your ability to build pipeline, close complex deals, and generate new business will directly impact revenue and long-term success. If you are a true hunter with experience in the POS fintech space and thrive on winning new logos — we want to hear from you!


Director of Sales Benefits and Compensation:

• Remote

• Competitive base salary with uncapped commission potential

• Performance-based incentives tied to revenue and profitability goals

• Comprehensive medical, dental, and vision insurance

• Paid time off and holidays

• 401k

• Mileage reimbursement and travel expense coverage

• Ongoing professional development and industry training opportunities

• Flexible, results-driven work environment


Director of Sales Requirements & Qualifications:

• Minimum 5 years of quota-carrying sales experience within the payments or point-of-sale industry

• Proven track record of generating pipeline and closing net-new business (hunter mentality required)

• Strong experience selling payment terminals, merchant services, or POS solutions

• Experience working with or through payment processors, ISVs, VARs, or enterprise retail clients

• Established network within payment processors, ISOs, or retail organizations

• Ability to prospect, qualify, and close complex deals in a long sales cycle environment

• Maintain accurate sales forecasts, pipeline tracking, and reporting to support business planning and performance visibility

• Actively identify and pursue high-value POS opportunities, focusing on accounts that deliver strong ROI

• Develop and execute territory and pipeline strategies aligned with revenue targets

• Build and maintain long-term client relationships while driving new business acquisition

• Collaborate cross-functionally with internal teams including operations, product, and customer support to successfully close and deliver business

• Bachelor’s degree in business, marketing, or related field (or equivalent experience)


Director of Sales Preferred Background & Skills:

• Strong communication, negotiation, and problem-solving skills with the ability to navigate complex sales environments

• Experience selling through channel ecosystems (ISV, VAR, ISO)

• Demonstrated ability to manage long sales cycles and multi-stakeholder deals

• Highly motivated, self-directed, and comfortable operating as a pure individual contributor