Director, Sales, Flex Pay

About the role

Upgrade is seeking a seasoned sales leader to drive the expansion of its Flex Pay Buy Now, Pay Later (BNPL) offering within the retail sector. This individual will be instrumental in generating new business, forging key merchant relationships, and growing the company's presence in the BNPL market. The successful candidate will own the end-to-end sales cycle for strategic partnerships, translating complex product capabilities into clear business value for enterprise clients. They will act as the primary commercial partner for a portfolio of retail and e-commerce brands, aligning Upgrade's Flex Pay solution with their growth objectives. This role requires a proactive leader who can navigate complex organizational landscapes to secure and expand business within a highly competitive financial services environment. The position demands a deep commitment to building trust and credibility with merchant stakeholders at all levels. Ultimately, this hire will be accountable for defining the commercial trajectory of the Flex Pay retail sales initiative through data-driven execution and strategic relationship management.

Key facts

What you'll do

• Acquire new enterprise and mid-market retail clients for the Flex Pay product through proactive prospecting, rigorous qualification, and disciplined closing of complex deals.
• Develop and present sophisticated sales proposals, respond to detailed RFPs, and expertly manage multi-stage contract negotiations from initial discussions through final execution.
• Design and execute a data-informed sales strategy that drives revenue growth and market share expansion while continuously optimizing core sales processes and workflows.
• Collaborate cross-functionally with Product, Design, Data, Risk, Marketing, and Legal teams to provide critical market feedback and influence the evolution of the Flex Pay product suite.
• Build and maintain strategic alliances with key merchants, payment service providers, e-commerce platforms, and major digital wallet providers to secure preferential placement and integration opportunities.
• Own and manage a comprehensive sales pipeline, accurately forecasting revenue, and ensuring consistent achievement of ambitious performance objectives and quotas.
• Leverage deep market intelligence and direct customer feedback to refine sales tactics, positioning, and messaging while informing product development priorities.
• Identify and penetrate new vertical segments within the retail and e-commerce space to uncover additional use cases and revenue opportunities for the Flex Pay solution.
• Serve as the primary escalation point for complex commercial and contractual matters, ensuring timely resolution and preservation of key relationships.
• Mentor and develop junior sales representatives, sharing best practices and coaching to elevate the overall performance of the Flex Pay Retail Sales team.
• Conduct comprehensive competitive analysis to identify gaps and advantages, enabling the team to position Flex Pay effectively against alternative payment solutions.
• Establish and monitor key performance indicators, adjusting strategies in real-time to maximize efficiency and return on sales efforts.
• Partner with Finance to model deal structures, evaluate credit risk implications, and ensure all commercial engagements meet company guidelines and profitability thresholds.
• Act as the brand ambassador for Upgrade's Flex Pay initiative, representing the company at industry conferences, webinars, and targeted retail events.

Requirements

• 8 to 10 years of progressive sales leadership experience within the Buy Now, Pay Later or broader payments industry, with a demonstrated track record of success.
• Comprehensive and current knowledge of prevailing BNPL industry trends, core payment technologies, the retail and e-commerce landscape, and the competitive ecosystem of payment service providers.
• A proven history of consistently exceeding ambitious revenue goals and quota attainment in dynamic, fast-paced, and highly competitive market conditions.
• Exceptional abilities in verbal and written communication, complex negotiation, and closing strategic partnerships at the enterprise level.
• A Bachelor's degree in business administration, finance, economics, or a closely related discipline is required.
• Demonstrated experience managing and exceeding demanding sales quotas in a B2B environment over an extended period.
• Strong judgment and integrity when handling confidential commercial information and navigating sensitive stakeholder discussions.
• The capability to travel domestically for client meetings, industry conferences, and strategic business development activities as required.
• Self-motivated with a high degree of ownership, accountability, and the discipline to manage a complex workload independently.
• Proficiency with standard sales and productivity software tools, including CRM platforms, spreadsheets, and presentation software.
• Willingness to adhere to company policies, procedures, and compliance standards governing financial services sales operations.
• Alignment with Upgrade's core values of transparency, integrity, and a commitment to providing equitable financial access.

Nice to have

• A Master of Business Administration (MBA) degree or equivalent advanced business qualification.

Practical notes

• This is a full-time position based in the United States and eligible for Flex Pay arrangements.
• Compensation details, including base salary and equity components, are determined by candidate qualifications and are considered competitive within the industry.
• Benefits may include comprehensive medical, dental, and vision insurance with employer contributions, flexible paid time off, paid parental leave, and participation in health and wellness programs.
• Professional development opportunities are available to support continued growth in the financial services sector.
• California residents will receive specific notice regarding the collection and handling of personal information in accordance with applicable privacy regulations.
• The successful candidate must be able to pass a background check and meet all regulatory compliance requirements for employment in financial services.
• This role requires occasional domestic travel and participation in industry events, with arrangements made in accordance with company policy.
• All employment decisions are made in compliance with Equal Employment Opportunity laws and company guidelines.