Director, Sales, Flex Pay

Upgrade; United States; Hybrid; USD 180,000 - 240,000; Full time

Benefits offered by this job

Stock options

Medical insurance

Dental insurance

Vision insurance

Flexible PTO

Professional growth

Job summary

Upgrade is seeking an experienced Director of Sales to lead the Flex Pay BNPL retail team. You will drive revenue growth by signing Enterprise and Mid‑Market merchants and building strategic partnerships.

This senior IC will own the full sales cycle from prospecting to close, collaborate with product and risk teams, and set a data‑driven strategy to expand market presence.

Join a fast‑paced growth environment and help shape BNPL adoption across retailers and e‑commerce platforms.

Qualifications

• 8–10 years of progressive sales leadership experience in BNPL or payments.
• Deep knowledge of BNPL, payments tech, retail and e‑commerce ecosystems.
• Proven track record of hitting ambitious revenue targets in a fast‑paced market.
• Excellent communication, negotiation, and deal closure skills.
• Bachelor’s or MBA in business or finance; MBA preferred.

Responsibilities

• Drive net-new business for Flex Pay by prospecting, qualifying, nurturing, and closing Enterprise and Mid‑Market merchants.
• Create consultative sales presentations, RFPs, and own end‑to‑end contract negotiations.
• Develop data‑driven sales strategies aligned with company goals to drive revenue growth.
• Collaborate with Product, Design, Data, Risk, Marketing, Legal, and other teams to improve the offer.
• Identify and cultivate strategic partnerships with merchants, PSPs, e‑commerce platforms, and wallets.
• Own sales targets, pipeline management, and forecasting to meet KPIs.
• Leverage market insights to refine sales approaches and inform product development.

Skills

Enterprise sales

Mid‑Market sales

BNPL/payments knowledge

Negotiation

Strategic partnerships

Forecasting

Cross-functional collaboration

Education

Bachelor’s degree in business, finance, or related field

MBA preferred

Job description

About the Role

We are seeking an experienced and strategic Director of Sales to join our Flex Pay BNPL retail team. This person will play a pivotal role in driving revenue growth, building strategic partnerships, and expanding our footprint in BNPL. This senior level IC will prospect, nurture, and sign a robust pipeline of Enterprise and Mid‑Market merchants to drive net new Flex Pay merchant acquisition. We are looking for a self-starter who can thrive in a fast-paced growth environment to take Flex Pay to the next level.

What You’ll Do

• Drive net-new business for Flex Pay by prospecting, qualifying, nurturing, and closing Enterprise and Mid‑Market retail merchants.
• Create consultative sales presentations, RFP proposals, and own the end‑to‑end contract negotiation process for new opportunities.
• Develop and implement a data‑driven sales strategy aligned with company goals to drive revenue growth and market penetration, while streamlining sales processes.
• Work closely with Product, Design, Data, Risk, Marketing, Legal, and other teams to ensure the Flex Pay team is continuously improving the product offering.
• Identify and cultivate strategic partnerships with merchants, PSPs, e‑commerce platforms, and digital wallets to expand adoption of BNPL solutions.
• Own sales targets, pipeline management, and forecasting, ensuring consistent achievement of KPIs and revenue goals.
• Leverage customer feedback, market insights, and industry trends to refine sales approaches and inform product development and adoption.

What We Look For

• 8‑10 years of progressive sales leadership experience within BNPL or payments space.
• Deep understanding of the BNPL landscape, payment technologies, retail, e‑commerce ecosystems, and payments service providers (PSPs).
• Track record of achieving ambitious revenue targets in a fast‑paced, competitive market.
• Excellent communication, negotiation, and deal closing skills.
• Education: Bachelor’s degree in business, finance, or a related field; MBA preferred.

What We Offer You

• Competitive salary and stock option plan.
• Medical, dental and vision insurance with employer paid options.
• Flexible PTO.
• Opportunities for professional growth and development.
• Work is performed indoors in a fast‑paced environment that requires the ability to manage multiple priorities and meet established workflows, schedules, and service expectations.
• Employees regularly input, retrieve, and exchange information accurately using digital systems and applications to support operational and customer service objectives.
• The role requires the ability to receive and exchange information with customers, peers, supervisors, and cross‑functional partners through available communication channels, which may include meetings, email, phone, and digital collaboration tools, and may involve real‑time, verbal, or in‑person exchanges depending on business need.
• Job duties may involve managing a high volume of inbound and/or outbound customer interactions and work activities using telecommunications and computer systems. The role requires the ability to read, analyze, and interpret information displayed on computer screens and remain in a working posture for extended periods, consistent with the demands of the position.
• Work may be performed in a contact center, office, or remote environment, depending on business needs and the nature of the role. Onsite work environments may include shared workspaces, standard office lighting, and moderate background noise typical of customer service or operational settings.
• Employees working remotely are responsible for maintaining a secure and productive workspace with reliable internet connectivity that supports company systems and safeguards the confidentiality of company and customer information.

Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions of the position in accordance with the Americans with Disabilities Act (ADA) and applicable state and local laws.

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.