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Salary: USD 245,000 - 293,000 / annual
Upside is transforming brick-and-mortar commerce by applying online retail sophistication—profit measurement, attribution, and incrementality—to help consumers earn 2-3x more cashback and provide retailers with profitable customer acquisition. Billions of dollars in commerce flow through the Upside platform annually.
You will lead the Merchant & Pay engineering hive, responsible for the retailer and partner side of this multi-sided marketplace. This includes Pay (in-flow payments experience) and internal tooling for operational partners. You'll manage multiple engineering managers and teams across domains, partnering closely with Product, Data, and other Engineering hives to ensure merchant and partner systems are reliable, scalable, secure, and strategically aligned.
Key responsibilities include:
- Owning technical strategy and multi-year roadmap for merchant/partner-facing systems, internal tooling, and incrementality/offer-gen IP
- Managing and growing engineering managers and their teams, setting high bars for technical and people leadership
- Creating a safe, collaborative environment that learns from incidents without blame
- Raising quality, performance, and engineering standards across all services
- Championing generative AI integration into engineering workflows
- Providing clarity and empowering autonomy across teams
- Partnering with Product, Data, Security, and other Engineering hives
- Representing Merchant & Pay in cross-functional planning and technical councils
- Supporting recruiting, development, and retention of high-caliber engineers; building diverse, high-performance culture
You thrive at the intersection of systems and storytelling—building robust solutions while communicating their purpose and impact. You challenge the status quo when it improves outcomes, learn from peers, and use data to advocate for informed change. You care about resilient, scalable systems and know when to invest in observability, automation, and infrastructure to reduce toil.
REQUIREMENTS:
- 10+ years of engineering leadership experience, including 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; pragmatic about performance, reliability, and cost tradeoffs
- Track record scaling platforms and partner integrations supporting millions of users and enterprise-grade partners
- Experience integrating generative AI into engineering workflows
- Clear communication across technical and non-technical audiences; ability to translate complex tradeoffs into roadmaps balancing speed, quality, and long-term business value
- Value clarity over consensus; help teams stay aligned through high-change, high-growth conditions
- Strong command of security, privacy, and compliance best practices; experience with sensitive consumer data and payments preferred
