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Whatnot Logo Whatnot · IT - Administration

Senior Systems Administrator

United States, Los Angeles, San Francisco, Phoenix, New York 150000.00 - 210000.00 USD / Year · Job Posted February 18, 2026
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Job Description

The Senior Systems Administrator plays a critical role in building, maintaining, and scaling the systems that power Whatnot’s post-purchase support experience. This role partners closely with Operations, Product, Engineering, and Support teams to ensure our tools and workflows enable high-quality, efficient support for buyers and sellers as the platform grows.

Job Responsibility

  • Own the administration, configuration, and ongoing improvement of post-purchase support systems, including Zendesk and related tooling across Customer Experience and Trust & Risk, supporting thousands of agents across our in-house team and multiple vendors
  • Ensure systems are configured to support operational workflows, user experience requirements, and evolving business needs
  • Partner with operations and business stakeholders to translate short- and long-term requirements into scalable system solutions and a product roadmap
  • Manage integrations between Zendesk and other internal systems to ensure data accuracy, reliability, and end-to-end visibility
  • Monitor vendor relationship and system performance, troubleshoot issues, and drive timely resolution to minimize disruption to support operations
  • Design, document, and maintain workflows, automations, permissions, and reporting to improve efficiency and consistency
  • Support system releases and enhancements, including testing, documentation, training, and change management
  • Identify opportunities to improve tooling, processes, and system architecture to support scale, reliability, and high-quality user support

Requirements

  • 8+ years of experience in Customer Support systems administration
  • Proven experience leading administration of Zendesk and 1+ other customer support platform (e.g., Salesforce Service Cloud, Intercom) at scale, supporting thousands of internal and off-shore agents across 4+ sites (system certifications preferred)
  • Solid understanding of post-purchase operations, including Customer Experience, Trust & Risk, WFM, and QA use cases
  • Experience managing system integrations, configuring APIs, data flows, and automations by working with internal tooling partners
  • Strong technical skills, including proficiency in HTML, JavaScript, JSON, SQL, and Python
  • Ability to gather requirements from non-technical stakeholders and translate them into scalable system solutions
  • Strong troubleshooting skills and comfort managing day-to-day system operations and incidents
  • Detail-oriented mindset with a focus on system configuration, permissions, governance, and data integrity
  • Strong documentation and communication skills, with the ability to support training and change management
  • Comfort balancing strategic improvements with hands-on execution in a high-growth environment

What we offer

  • Generous Holiday and Time off Policy
  • Health Insurance options including Medical, Dental, Vision
  • Work From Home Support
  • Home office setup allowance
  • Monthly allowance for cell phone and internet
  • Care benefits
  • Monthly allowance for wellness
  • Annual allowance towards Childcare
  • Lifetime benefit for family planning, such as adoption or fertility expenses
  • Retirement
  • 401k offering for Traditional and Roth accounts in the US (employer match up to 4% of base salary) and Pension plans internationally
  • Monthly allowance to dogfood the app
  • Parental Leave
  • 16 weeks of paid parental leave + one month gradual return to work
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