About The Position

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. Whatnot is the largest livestream shopping platform in North America and Europe to buy, sell, and discover the things you love. We're building live commerce at a scale that's never been done in the West, and there's no playbook to copy. The people here are shaping how an entirely new industry develops. As a remote co-located team, we're inspired by our values and anchored in hubs across the US, UK, Ireland, Poland, Germany, and Australia. We move fast, stay close to our users, and focus on the work that drives the most impact. We're one of the fastest growing marketplaces and were recently named the #1 Best Startup Employer in America by Forbes.

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

Responsibilities

  • 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

Benefits

  • 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
  • 16 weeks of paid parental leave + one month gradual return to work company leave allowances run concurrently with country leave requirements which take precedence.
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