Senior Director, Marketplace Operations & Health

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 the Marketplace Operations & System Health team: The Marketplace Operations & System Health team is passionate about building the data integrity layer that keeps Upside's marketplace trusted, reliable, and primed for growth. We are a curious, action-oriented group who thrive at the intersection of data, operations, and product — equally energized by preventing the next incident and engineering systems that make firefighting obsolete. We collaborate closely with Engineering, Data, and our commercial partners across the organization, and foster an environment where diverse perspectives and continuous improvement aren't just encouraged — they're how we get better every day. Specifically, you will: - Own the end-to-end optimization and health of Upside’s marketplace operations. From retailer data pipelines through Upside’s marketplace systems. - Identify opportunities to drive overall growth and accelerate strategic initiatives through optimization and tuning of Upside’s marketplace - Execute, deliver and report on strategies to accelerate growth and drive strategic initiatives - Define and deliver a continuous improvement roadmap to CPO-level leadership, surfacing trends, patterns, and systemic risks before they impact merchants or consumers - Define the monitoring model, alerting thresholds, and SLAs that underpin marketplace reliability - Build and operate a layered health model that detects anomalies, data quality failures, and marketplace disruptions in real time, managing “data downtime” as a key performance indicator - Lead the incident lifecycle for data and quality failures: own detection, triage, resolution, and post-mortem review — ensuring continuous improvement and reduced time-to-resolution - Embed Lean/Six Sigma discipline (DMAIC and similar frameworks) to systematically reduce the root causes of quality issues, moving the team from reactive firefighting to proactive prevention - Push validation and self-healing capabilities upstream into the core product — reducing manual intervention at scale. - Partner closely across the entire company, particularly with Product, Engineering, Data Engineering and B2B/B2C commercial teams - Manage and develop the Marketplace Operations team (currently 3 ICs), providing strategic direction, coaching, and cross-functional coordination - AI centric approach to monitoring, investigating and scaling operations What you should have - 7+ years in data operations, marketplace/platform ops, or system data reliability engineering with a business focus to drive revenue and GMV growth - Cross-functional leadership experience across Data Engineering, Ops, Marketing and GTM/Sales - Incident management and post-mortem ownership (owns “data downtime” as a KPI) - Experience building health monitoring frameworks at scale (alerting, SLAs, dashboards) - Strong data literacy and analytical fluency (SQL, data pipeline awareness) - Track record of driving systematic improvement — not just firefighting The fine print: 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 US base salary range for this full-time position is $220,000 - $