Senior Systems Administrator, Operations

Whatnot•Los Angeles, CA

10d•Hybrid

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. 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.

Requirements

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