Upside Business Travel

Senior Director, Marketplace Operations & Health

Upside Business Travel$220K — $256K *
Consumer Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 7+ years in data operations, marketplace/platform ops, or system data reliability engineering
  • Cross-functional leadership experience across Data Engineering, Ops, Marketing, and GTM/Sales
  • Incident management and post-mortem ownership regarding data downtime
  • Experience building health monitoring frameworks at scale
  • Strong data literacy and analytical fluency, including SQL
  • Track record of driving systematic improvement instead of reactive firefighting

Responsibilities

  • Own end-to-end optimization and health of Upside's marketplace operations
  • Identify growth opportunities and accelerate strategic initiatives through optimization
  • Define and deliver a continuous improvement roadmap to CPO-level leadership
  • Establish monitoring models, alerting thresholds, and SLAs for marketplace reliability
  • Lead the incident lifecycle for data and quality failures, ensuring continuous improvement
  • Embed Lean/Six Sigma principles to reduce root causes of quality issues
  • Partner across the company with Product, Engineering, and commercial teams
  • Manage and develop the Marketplace Operations team, providing strategic direction

Benefits

  • Medical, dental, and vision coverage starting on Day 1
  • Equity offerings such as ISOs
  • 401(k) program
  • Family planning programs and paid parental leave
  • Physical fitness and wellness memberships
  • Emotional and mental health support programs
  • Unlimited PTO and 10 paid federal holidays
  • Flexible work environment with specific in-office days
  • Lunch reimbursement for in-office employees
  • Learning and Development stipend
  • Transparent culture and Employee Resource Groups
  • Commitment to an amazing mission
Full Job Description
Specifically, you will:
  • 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


What you should have
  • 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


The fine print:

Location: 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.

Compensation: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. Your recruiter can share more about the specific salary range during the hiring process.

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
  • Amazing mission!


About Upside Business Travel

Upside Business Travel is a travel management company that offers a platform for booking business travel. The company was founded in 2015 by Jay Walker, the founder of Priceline.com. Upside Business Travel's platform allows users to book flights, hotels, and rental cars in one place. The company also offers a rewards program that gives users gift cards for booking travel. Upside Business Travel has raised over $50 million in funding.
Learn more about Upside Business Travel
Size
100 employees
Industry
Founded
2018

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