Senior Director, Marketplace Operations & Health

Marketplace Operations & System Health Team

We are a curious, action‑oriented group who thrive at the intersection of data, operations, and product. We collaborate closely with Engineering, Data and our commercial partners across the organization, fostering an environment where diverse perspectives and continuous improvement are not just encouraged – they’re how we get better every day.

• 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.

• 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.

Hybrid role – based in one of our Austin, Chicago, DC, or NYC offices. 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.

The US base salary range 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.

• 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 and a week‑long Winter Break.
• Flexible work environment.
• Lunch reimbursement for in‑office employees.
• Employee Resource Groups.
• Learning and Development stipend.
• Transparent culture.

Diversity drives innovation, and our differences make us stronger. We’re passionate about building a workplace that represents a variety of backgrounds, skills and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status. Everyone is welcome here.

If there’s anything we can do to support a disability or special need during your application or interview process, please email