Senior Director, Marketplace Operations & Health

Upside•Washington, DC

1d•$220,000 - $256,000•Hybrid

About The Position

Upside aims to transform brick-and-mortar commerce by applying the sophistication of online retail, including profit measurement, attribution, and incrementality, to offer users greater value on everyday purchases and attract new, profitable customers to brick-and-mortar businesses. The company has enabled millions of users to earn significantly more cashback than other platforms and has helped hundreds of thousands of businesses achieve measurable profit. Billions of dollars in commerce flow through the Upside platform annually, benefiting retailers, consumers, and sustainability initiatives. The Marketplace Operations & System Health team is dedicated to establishing a data integrity layer that ensures Upside's marketplace is trustworthy, reliable, and positioned for growth. This team is composed of curious, action-oriented individuals who excel at the intersection of data, operations, and product. They are motivated by both preventing future incidents and engineering systems that eliminate the need for reactive problem-solving. The team collaborates closely with Engineering, Data, and commercial partners across the organization, fostering an environment where diverse perspectives and continuous improvement are integral to daily progress.

Requirements

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.

Responsibilities

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.
Utilize an AI-centric approach to monitoring, investigating, and scaling operations.