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Director, Sales, Flex Pay

Upgrade · United States (Remote)

Posted about 2 months ago

or apply directly on Upgrade's site. We never take the application ourselves.

Is this posting real?

This role has been open
51 days
Upgrade's roles stay open a median of 51 days
Reposted
No
Salary listed
No
20% of Upgrade's roles list one
Ghost-job risk at Upgrade
high
13 stale, 0 reposted of 25 open
Hiring momentum
32 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-09-24

Measured from postings appearing on and disappearing from Upgrade's own greenhouse board since 2026-08-03. Full hiring picture for Upgrade.

About this role

The Director of Sales for Flex Pay will be responsible for driving revenue growth by acquiring new Enterprise and Mid-Market retail merchants. This role involves creating sales presentations, negotiating contracts, and developing a data-driven sales strategy while collaborating with various teams to enhance product offerings. The position requires a self-starter capable of thriving in a fast-paced environment to expand the BNPL footprint.

Our read on this posting2.4out of 5
benefits
3/5
freshness
1/5
career value
4/5
role clarity
4/5
pay transparency
0/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Upgrade as an employer.

What you 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
  • Bachelor’s degree in business, finance, or a related field; MBA preferred

What you get

  • Competitive salary and stock option plan
  • Medical, dental and vision insurance with employer paid options
  • Flexible PTO
  • Opportunities for professional growth and development
  • Paid parental leave
  • Health & wellness initiatives

Worth weighing

  • No specific salary listed
  • The role involves a high volume of customer interactions, which may be demanding
  • The position requires the ability to work in a fast-paced environment with multiple priorities

Summarised from Upgrade's posting. Read the full original.

Listed by Upgrade on their greenhouse job board, last confirmed open on 2026-09-24. PitchMeAI is not the employer.

More roles at Upgrade

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