Senior Director, Marketplace Operations & Health

About the role

The Marketplace Operations & System Health team at Upside is responsible for ensuring the trust, reliability, and growth of the marketplace. We work closely with Engineering, Data, and various commercial partners to prevent incidents and improve system health.

Responsibilities

• Identify and drive opportunities to grow the marketplace through optimization and strategic initiatives.
• Deliver and report on strategies to accelerate growth and drive strategic initiatives.
• Define and implement a continuous improvement roadmap for CPO-level leadership, focusing on trends, patterns, and systemic risks.
• Build and operate a real-time health model that detects anomalies, data quality failures, and marketplace disruptions, managing these as key performance indicators.
• Lead the incident lifecycle, from detection to resolution, ensuring continuous improvement and reduced time-to-resolution.
• Embed Lean/Six Sigma principles to systematically reduce root causes of quality issues, transitioning 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, providing strategic direction, coaching, and cross-functional coordination.
• Implement an AI-centric approach to monitoring, investigating, and scaling operations.

Requirements

• 7+ years of experience 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.
• Experience with incident management and post-mortem ownership, owning "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).
• A 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 cloud-based infrastructure and services.

Skills

• Data analysis and interpretation.
• Problem-solving and critical thinking.
• Collaboration and communication skills.
• Leadership and team management.
• Technical proficiency in relevant software and tools.

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.