[Hiring] Senior Systems Administrator / Engineer @Little Sleepies

Role Description

Little Sleepies is growing fast, and so is the systems and automation backbone that keeps us moving. We are looking for a Senior Systems Administrator / Engineer to join our Systems team and take hands-on ownership of the platforms and automations our teams rely on every day. This is a balanced role: part enterprise systems administrator keeping our core applications healthy and well supported, and part automation engineer building the integrations and workflows that let a lean team punch well above its weight.

You will work closely with the Director of Systems and partner with teams across Photography, Product, Compliance and Integrity, Production, Marketing, Lifecycle, eCommerce, and Finance. Day to day, you will build and improve automations in tools like Airtable and n8n, write scripts and API integrations that connect our systems, and provide high-touch support that keeps everyone unblocked. We lean into modern, AI-assisted development, so you will use tools like Claude to build, document, and maintain solutions quickly and thoughtfully. If you love turning manual, error-prone processes into clean, reliable, automated ones, and you like owning systems end to end, this role is for you.

What you’ll do:

• Design, build, and maintain automations and integrations across our stack using n8n, APIs, webhooks, and custom scripts, connecting systems so data flows reliably between them.
• Own and continuously improve our Airtable environment, including bases, interfaces, automations, and scripting, that Photography, Compliance and Integrity, and Production use to run their day-to-day work, tightening timelines and reducing manual effort.
• Use AI-assisted development tools such as Claude to accelerate how you build, document, and maintain automations, scripts, and integrations.
• Handle day-to-day administration of our enterprise applications, including NetSuite (users, roles and permissions, saved searches, record and field maintenance), and troubleshoot sync issues across NetSuite, Shopify, and connected systems.
• Provide high-touch, systems-specific technical support that goes beyond first-line helpdesk, and serve as a reliable second owner and backup across our automations and enterprise systems.
• Help monitor and maintain our data pipelines and Snowflake environment so Marketing, Lifecycle, Finance, and Analytics teams have dependable, timely data.
• Document systems, workflows, and runbooks, and follow through with continuous improvements after issues are resolved.

Qualifications

• 5+ years in systems administration, IT engineering, or automation and integration engineering, ideally in a fast-moving company.
• Advanced Airtable or similar relation database systems expertise, including complex bases, interfaces, automations, and scripting.
• Strong workflow automation experience with n8n (or a comparable platform) and a track record of building API and webhook integrations between SaaS systems.
• Solid scripting skills (JavaScript and/or Python) and comfort working with REST APIs, webhooks, and authentication such as OAuth.
• Hands-on experience using AI coding tools such as Claude to build and maintain automations and integrations.
• Experience administering enterprise business applications, including NetSuite (users, roles, saved searches, and general administration).
• Strong troubleshooting instincts, a bias for ownership and follow-through, clear documentation habits, and the ability to communicate with both technical and non-technical partners.

Requirements

• Experience with Snowflake, dbt, and SQL for monitoring and maintaining data pipelines.
• Identity and access administration (Okta), endpoint management (Jamf and/or Intune), and Google Workspace administration.
• Experience supporting e-commerce and retail operations systems such as Shopify Plus, digital asset management platforms, and customer experience platforms such as Zendesk, Gladly, or Richpanel.
• Experience supporting data, analytics, and finance reporting needs.

Benefits

• Health, dental, and vision insurance
• Paid time off, vacation
• Sick days
• Paid holidays
• Short and long-term disability
• Life insurance
• 401(k)
• Employee Assistance Program
• Flexible Spending Accounts
• Home office stipend
• Internet stipend
• Company discount
• Team building activities
• Company-issued computer