Senior Systems Administrator, Operations

Overview

Join the Future of Commerce with Whatnot! Whatnot is the largest live shopping platform in North America and Europe to buy, sell, and discover the things you love. We’re redefining e-commerce by blending community, shopping, and entertainment into a community just for you. As a remote co-located team, we’re inspired by innovation and anchored in our values. With hubs in the US, UK, Germany, Ireland, and Poland, we’re building the future of online marketplaces – together.

From fashion, beauty, and electronics to collectibles like trading cards, comic books, and even live plants, our live auctions have something for everyone.

And we’re just getting started! As one of the fastest growing marketplaces, we’re looking for bold, forward-thinking problem solvers across all functional areas. Check out the latest Whatnot updates on our news and engineering blogs and join us as we enable anyone to turn their passion into a business, and bring people together through commerce.

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. In this role, you will:

• 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

We offer flexibility to work from home or from one of our global office hubs, and we value in-person time for planning, problem-solving, and connection. Team members in this role are required to be within commuting distance of our New York, San Francisco, Phoenix, or Los Angeles hubs.

Curious about who thrives at Whatnot? We’ve found that low ego, a growth mindset, and a bias toward action go a long way here. As our Senior Systems Administrator, you bring strong technical expertise and an operations mindset, and you enjoy working closely with business and support teams to build systems that enable high-quality user experiences. You should have 8+ years of experience in Customer Support systems administration, plus:

• 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…