Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families (plus Wired and the Wirecutter). Our latest product is Calendar 2, which just launched to rave reviews.

Our mission is to connect loved ones by creating the world’s simplest products and services that improve family life. Our founders are former venture capitalists and serial entrepreneurs who have scaled this business to $300M+ in annual revenue while being completely bootstrapped and profitable. We get to grow a happy, healthy company focused on making products our customers love without investors breathing down our necks.

Smart, hardworking people who care about making actually meaningful products love working here. People like you. We’re busy inventing new ways to simplify family life and help parents raise great kids – and we need your help! Come invent something new with us.

About The Role

We’re hiring our first Director of IT. IT at Skylight exists to do two things: make us faster/more effective, and make us safer/more secure. In this role, you’ll own the full IT function, from onboarding new hires to managing vendors, from fielding daily requests to building the systems that make those requests go away. You’ll report to the VP of Engineering and work closely with our Head of Security and Head of People & Culture.

This is a hands-on role. Call it “full stack” IT. You’ll be the person employees turn to when something’s broken, and the person building the infrastructure that keeps things from breaking in the first place.

A few things to know about Skylight before you apply:

1. We’re not in a heavily regulated industry, so any compliance we do (beyond PCI SAQ-A) is voluntary. We don’t believe in box-ticking or security theater; we believe in rigorous, practical protection of our customers’ data.
2. We place high value on autonomy. You’ll have real ownership here, not just of the ticket queue, but of the strategy. No hand-holding. No micromanagement.
3. We believe in using AI and automation to simplify and streamline our workflows. If you can make something self-serve or automated, do it. Need a new tool to make that happen? Let’s get it.

Responsibilities

• Own employee onboarding and offboarding end-to-end: accounts, devices, access provisioning, group membership, device return, etc.
• Manage the company device fleet across Mac and Windows, including procurement, setup, configuration, lifecycle management, and asset tracking..
• Handle day-to-day IT requests and, wherever possible, replace them with automation and self-serve tooling that reduces repetitive support work..
• Own vendor relationships, contracts, and renewals across our SaaS stack, negotiating on our behalf and keeping spend reasonable. 
• Administer our core tools: Google Workspace, Okta, 1Password, Slack, Justworks, Ramp, and whatever else we add over time.
• Conduct periodic access reviews and maintain a clean, current view of user access across core systems, with a focus on least privilege.
• Contribute to IT and security policy documentation, keeping it practical and usable rather than shelfware.
• Support our Head of Security on incident response when needed.
• Evaluate and implement MDM and endpoint security solutions if and when we’re ready, and figure out what “the Skylight way” looks like for each.
• Maintain a clean internal systems environment, including license hygiene, admin role hygiene, and reduction of unnecessary access and tool sprawl.