Director, Engineering - Merchant & Pay

About this role

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.