Senior Account Executive

About GrailPay

GrailPay is the risk and data network for B2Bs. We give banks, payment processors, embedded fintech platforms, and lenders a real-time risk and data layer so they can approve more good payments and stop the bad ones before the money moves. Enterprise fintechs, payment companies, and financial institutions  have used GrailPay to cut return rates by more than two-thirds and push auto-approval rates above 95%, even through peak-volume periods. We're a fast-growing, fintech startup in New York building critical payments infrastructure — our sales team is still small, which means the next few hires will shape how GrailPay sells for years to come.

About the role

We're hiring a Senior Account Executive to own GrailPay's mid-to-large market motion — deals from roughly $150K to $500K in annual contract value, sold to fintechs, payment processors, and financial services companies that are past the SMB stage but not yet enterprise. We need someone who has already closed a meaningfully larger, more complex deal than the reps around them, and who can mentor newer AEs while doing it.

What you'll do

•  Build and own a pipeline of mid-market accounts across banking, embedded fintech, payment processors, and platforms

•  Run multi-threaded sales cycles involving VP- and executive-level stakeholders across risk, compliance, product, and engineering

•  Build account plans for target accounts, mapping stakeholders, buying process, and timeline

•  Lead discovery and demos

•  Serve as a trusted advisor to buyers on payments risk infrastructure

•  Mentor newer AEs on pipeline generation, discovery, and deal management

•  Maintain rigorous CRM hygiene and forecast accurately

•  Contribute directly to GrailPay's sales playbook, pricing, and competitive positioning as the team scales

What we're looking for

Required

•  4+ years of B2B sales experience with a consistent, provable record of hitting or exceeding quota on deals in the $150K–$500K+ range

•  A real sales pedigree — President's Club, top-performer recognition, or equivalent, more than once, with specifics you can walk through

•  Experience managing multi-stakeholder sales cycles with VP- and executive-level buyers

•  Experience selling into or alongside technical and risk/compliance teams

•  Comfort operating with minimal structure — you build your own process rather than needing one handed to you

•  Proficiency with CRM tools and a disciplined forecasting methodology

Preferred

•  Experience selling payments, risk, compliance, or financial infrastructure products

•  Existing network of relationships at banks, fintechs, or payments technology companies

•  Track record of helping build — not just run — a sales motion at an early-stage or growth-stage company

•  Working knowledge of ACH, wire, and check rails, and how technical buyers evaluate platforms like GrailPay's

Location & schedule

Based in New York, NY, in our office 4–5 days a week. We're a small team that leans on being in the room together, especially at this stage — you should want that too, not just tolerate it.

What we offer

•  Competitive base salary, commission, and equity

•  Comprehensive health, dental, and vision coverage

•  A direct hand in building GrailPay's mid-market playbook, with a clear path to more scope as the team grows

•  A workspace people actually like being in, everyday perks, celebrations that mark milestones, team events throughout the year, and the occasional friendly competition to keep things fun. We believe good work happens when people enjoy where — and who — they work with

GrailPay is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.