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, ensuring it remains trusted, reliable, and ready for growth. We work closely with Engineering, Data, and various commercial partners to prevent incidents and improve system efficiency.

Responsibilities

• Identify and implement strategies to drive growth and accelerate strategic initiatives through optimization and tuning of the marketplace.
• Develop and deliver a continuous improvement roadmap to CPO-level leadership, focusing on trends, patterns, and systemic risks.
• Define and operationalize a monitoring model, setting alerting thresholds and Service Level Agreements (SLAs) for marketplace reliability.
• Build and maintain a real-time health model capable of detecting anomalies, data quality failures, and marketplace disruptions.
• Lead the incident lifecycle, from detection to resolution, ensuring continuous improvement and minimized time-to-resolution.
• Promote a lean/six sigma approach to systematically reduce the root causes of quality issues, transitioning from reactive firefighting to proactive prevention.
• Partner with Product, Engineering, Data Engineering, and B2B/B2C commercial teams to manage and develop the Marketplace Operations team.
• Drive systematic improvements in data operations, system reliability, and overall marketplace performance.

Requirements

• At least 7 years of experience in data operations, marketplace/platform ops, or system data reliability engineering with a strong focus on revenue and GMV growth.
• Cross-functional leadership experience across Data Engineering, Operations, Marketing, and GTM/Sales.
• Proven experience in incident management and post-mortem analysis, prioritizing "data downtime" as a key performance indicator.
• Experience building and operating health monitoring frameworks at scale, including alerting, SLAs, and dashboards.
• Strong data literacy and analytical skills, including proficiency in SQL and data pipeline awareness.
• A track record of driving systematic improvement and reducing root causes of quality issues through systematic approaches.

Qualifications

• Business acumen and a deep understanding of the retail and e-commerce landscape.
• Ability to work effectively in a fast-paced, dynamic environment with multiple stakeholders.
• Excellent communication and collaboration skills to work closely with cross-functional teams.
• Passion for using data-driven insights to inform decision-making and drive business outcomes.

Skills

• Data pipeline design and implementation.
• Alerting and monitoring systems development.
• Lean/Six Sigma methodologies for process improvement.
• Marketplace operations and system reliability engineering.
• Collaboration and partnership with cross-functional teams.

Benefits

• Medical, dental, and vision coverage starting on Day 1.
• Equity (ISOs).
• 401(k) program.
• Family planning programs and 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.