Director, Engineering – Merchant & Pay

Upside

. Lead the Merchant & Pay hive responsible for retailer and partner systems, in-flow payments, and internal operational tooling .

Posted 10/2/2026full-timeUnited StatesLead💰 $245,000 - $293,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive engineering leadership with a focus on managing complex, business-critical systems and integrating generative AI into workflows. Proven ability to build high-performance teams and foster a diverse culture while ensuring compliance with security and privacy best practices.

Highest-signal resume keywords

Engineering LeadershipGenerative AI IntegrationAWS Solution DesignB2B2C Systems ManagementSecurity and Compliance Best Practices

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Engineering LeadershipComplex Systems ManagementGenerative AI IntegrationAWS Solution DesignPlatform ScalingPartner IntegrationOKR DevelopmentTechnical StrategyPerformance StandardsData Privacy

Soft Skills

Clear CommunicationTeam BuildingCollaborationMentoringDiversity Advocacy

Industry Keywords

Merchant SystemsPartner SystemsPayments SystemsB2B2CMarketplace DomainsConsumer Data HandlingOperational ToolingCross-Functional PlanningTechnical CouncilsSuccession Planning

Tech Stack

Tools & technologies

AWS

About the role

Key responsibilities & impact

Lead the Merchant & Pay hive responsible for retailer and partner systems, in-flow payments, and internal operational tooling
Own technical strategy and multi-year roadmap for merchant- and partner-facing systems, internal tooling, and incrementality/offer-generation IP
Translate strategy into quarterly plans and clear OKRs
Manage and grow engineering managers and their teams across multiple domains
Build a safe, collaborative, high-performance engineering environment
Raise quality, performance, and engineering standards across owned services and teams
Integrate generative AI into engineering workflows
Provide clarity, guardrails, and autonomy to managers and teams
Partner with Product, Data, Security, and other Engineering hives
Represent Merchant & Pay in cross-functional planning, technical councils, and leadership roadmap discussions
Support recruiting, developing, and retaining engineering managers and senior engineers
Build a diverse, high-performance culture with succession planning

Requirements

What you’ll need

10+ years of engineering leadership experience, including experience managing managers
Track record owning complex, business-critical systems end to end
Experience leading teams supporting merchant-, partner-, and/or payments-facing systems, or comparable B2B2C / marketplace domains
Comfortable designing and reviewing solutions in AWS
Track record scaling platforms and partner integrations supporting millions of users and enterprise-grade partners
Experience integrating generative AI into engineering workflows
Ability to communicate clearly across technical and non-technical audiences and translate complex tradeoffs into roadmaps
Strong command of security, privacy, and compliance best practices
Experience in environments handling sensitive consumer data and payments preferred
Ability to work in the Austin, Chicago, Washington, DC, or NYC office and attend in person Monday, Tuesday, and Thursday

Benefits

Comp & perks

Medical, dental, and vision coverage starting on Day 1
Equity (ISOs)
401(k) program
Family planning programs + paid parental leave
Physical fitness and wellness memberships
Emotional and mental health support programs
Unlimited PTO + 10 paid federal holidays + annual, week-long Winter Break
Flexible work environment
Lunch reimbursement for in-office employees
Employee Resource Groups
Learning and Development stipend
Transparent culture
Amazing mission