Senior Director, Marketplace Operations & Health

About the role

The Marketplace Operations & System Health team at Upside is responsible for maintaining the integrity of our marketplace, enabling growth, and driving revenue and GMV. We work closely with various teams including Engineering, Data, and commercial partners to ensure the reliability and efficiency of our systems.

Responsibilities

• Identify and implement strategies to drive overall growth and accelerate strategic initiatives through optimization and tuning of the marketplace.
• 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.
• 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.
• 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.

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.

Qualifications

• BS/MS in Computer Science, Statistics, or related field.
• Experience with data analytics tools and platforms.
• Understanding of data governance and compliance standards.
• Experience with monitoring and alerting systems.
• Knowledge of Lean/Six Sigma methodologies.

Skills

• Data analysis and interpretation.
• Problem-solving and critical thinking.
• Collaboration and communication skills.
• Project management and organizational skills.

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.

Pay

The US base salary range for this full-time position is $220,000 - $256,000 + equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions.

Schedule

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.