Director, Engineering - Merchant & Pay

Upside; Chicago (IL); Hybrid; USD 245,000 - 293,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Equity (ISOs)

401(k) program

Family planning programs + paid paren​

Flexible work environment

Lunch reimbursement

Learning and Development stipend

Transparent culture

Job summary

Upside is hiring a Director of Engineering to lead the Merchant & Pay hive, guiding the retailer and partner side of our multi-sided marketplace. You will manage managers and teams across multiple domains, partnering with Product, Data, and Security to keep merchant and partner systems reliable, scalable, and secure.

You will shape the long-term technical strategy, own the roadmap, and drive a high-performance culture with strong succession planning, while integrating generative AI to improve

Qualifications

• Have 10+ years of engineering leadership experience, including managing managers.
• Led teams supporting merchant-, partner-, and/or payments-facing systems.
• Experience designing solutions in AWS with performance, reliability, and cost considerations.
• Skilled at scaling platforms and integrations for millions of users and enterprise partners.
• Experience integrating generative AI into engineering workflows.

Responsibilities

• Lead with hive and company outcomes, prioritizing broader engineering success.
• Own the technical strategy and multi-year roadmap for merchant- and partner-facing systems.
• Manage and grow a team of engineering managers across the hive.
• Create a safe, collaborative environment and promote learning from incidents.
• Raise the bar on quality, performance, and standards across services.
• Champion AI integration to improve delivery speed and developer experience.
• Provide autonomy with clear expectations and guardrails for teams.
• Collaborate with Product, Data, Security, and other hives to meet business needs.
• Represent Merchant & Pay in planning and roadmap discussions with leadership.
• Support recruiting and retention of high-caliber engineers; foster a diverse culture.

Skills

Engineering leadership

Managing managers

Merchant & Pay systems

AWS architecture

Scaling platforms

Generative AI in engineering

Effective communication

Security and compliance

Tools

AWS

Job description

Meet Upside

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail-profit measurement, attribution, and incrementality to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We've helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.

Meet Upside

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail-profit measurement, attribution, and incrementality to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We've helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.

What You'll Do

We're looking for a Director, Engineering to lead our Merchant & Pay hive - the group responsible for the retailer and partner side of our multi-sided marketplace. This team includes Pay, our in-flow payments experience, as well as supporting internal tooling for some of our operational partners.

You'll combine strong technical judgment with people-first leadership, managing managers and teams across multiple domains, while partnering closely with Product, Data, and the other Engineering hives to keep merchant and partner systems reliable, scalable, secure, and aligned with company strategy.

Roles And Responsibilities

• Lead with hive and company outcomes over local optimization. You lean in wherever risk or opportunity exists across Merchant & Pay, regardless of team boundaries, and prioritize the success of the broader engineering org.
• Own the technical strategy and multi-year roadmap for merchant- and partner-facing systems, internal tooling, and incrementality/offer-gen IP, translating strategy into quarterly plans and clear OKRs.
• Manage and grow a team of engineering managers and their teams across the Merchant & Pay hive, setting a high bar for technical and people leadership.
• Create a safe, collaborative environment across your teams. You name problems, invite open discussion, and help teams learn from incidents and change without blame.
• Raise the bar on quality, performance, and engineering standards across every service and team you own.
• Champion the integration of generative AI into engineering workflows across the hive to improve delivery speed, quality, and developer experience.
• Provide clarity and empower autonomy — ensuring expectations and guardrails are clear enough that your managers and their teams can move quickly and independently.
• Partner closely with Product, Data, Security, and the other Engineering hives (Consumer, Platform) to ensure merchant and partner systems support current and emerging business needs.
• Represent Merchant & Pay in cross-functional planning, technical councils, and long-term roadmap discussions with company leadership.
• Support recruiting, developing, and retaining high-caliber engineering managers and senior engineers; build a diverse, high-performance culture with strong succession planning.

Professional Qualifications

• Have 10+ years of engineering leadership experience, including experience managing managers, and a track record owning complex, business-critical systems end to end.
• Have led teams supporting merchant-, partner-, and/or payments-facing systems, or comparable B2B2C / marketplace domains.
• Are comfortable designing and reviewing solutions in AWS, and can make pragmatic tradeoffs between performance, reliability, and cost.
• Have a track record scaling platforms and partner integrations that support millions of users and enterprise-grade partners.
• Have experience integrating generative AI into engineering workflows to improve delivery speed, quality, and developer experience.
• Communicate clearly across technical and non-technical audiences, and can translate complex tradeoffs into roadmaps that balance speed, quality, and long-term business value.
• Value clarity over consensus and help teams stay aligned through high-change, high-growth conditions.
• Strong command of security, privacy, and compliance best practices; experience in environments handling sensitive consumer data and payments preferred.

Why You Should Apply

• You aren't afraid to challenge the status quo when it makes the team and business better. You learn from those around you while utilizing data to advocate for informed change.
• You thrive at the intersection of systems and storytelling — not only building robust solutions but communicating their purpose, impact, and rationale, so teams can experiment, iterate, and act confidently.
• You care about building resilient systems that scale, and know when to invest in observability, automation, or new infrastructure to reduce toil and improve outcomes.

Location:

This hybrid role is based in our Austin, Chicago, DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday, and may increase based on project-based needs and changes to Upside's in-office policy over time.

Compensation

The U.S. base salary range for this full-time position varies by work location:

• Tier 1: NYC $270,000 - $293,000
• Tier 2: Austin, Chicago, Washington, DC $245,000 - $266,000

In addition to base salary, this position is also eligible for equity and benefits.

Benefits

• 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 + our 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!

Diversity And Inclusion

Diversity drives innovation, and our differences make us stronger. We're passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here! If there's anything we can do to support a disability or special need during your application or interview process, please email [e-mail]. This email is for accessibility accommodations only, it should not be used to submit job applications.

Compensation Range: $245K - $293K