Director, Sales – Flex Pay

Upgrade, Inc.

Director of Sales responsible for driving revenue growth and expanding partnerships within Flex Pay BNPL retail. Seeking experienced leader to increase Flex Pay merchant acquisition.

Posted 5/11/2026full-timeRemote • 🇺🇸 United StatesLeadWebsite

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

Competitive salary and stock option plan
100% paid coverage of medical, dental and vision insurance
Flexible PTO
Opportunities for professional growth and development
Paid parental leave
Health & wellness initiatives

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

sales strategycontract negotiationpipeline managementforecastingdata-driven decision makingRFP proposalsrevenue growthmarket penetrationKPI achievementcustomer feedback analysis

Soft Skills

communicationnegotiationdeal closingleadershipcollaborationstrategic thinkingrelationship buildingproblem solvingadaptabilitycustomer-centric approach

Certifications

Bachelor’s degreeMBA