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:

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
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
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

Requirements

5+ years in IT, with meaningful time owning IT operations at a company, not just supporting them
Deep, admin-level expertise in Google Workspace and Okta. Solid working knowledge of 1Password, Slack, Justworks, and Ramp is a big plus
Comfortable supporting both Mac and Windows environments
A solid foundation in information security controls relevant to IT, including access control, MFA, least privilege, phishing-resistant practices, and endpoint hygiene
A systems mindset. You don't just close tickets, you look for the pattern behind them and build solutions that reduce repeat work.
Comfort using AI tools (Claude Code/CoWork, or similar) to automate workflows, write scripts, and generally move faster than the job would otherwise allow
Clear, direct communication. You can explain a policy to a non-technical employee, write a runbook, and escalate a risk clearly to leadership
Comfort operating as a solo practitioner in a fast-moving environment, with the judgment to prioritize when everything feels urgent
Your users think you're the gosh-darned best

Benefits

Our competitive compensation package includes:

Competitive Salary + Equity Package
401K matching
Wellness, learning, and home-office budgets
Health, Dental & Vision Medical Plans
Tremendous autonomy to set the direction of your work
Unlimited PTO
Company holidays on the first Friday of every month (Except November & December)

Equal opportunity employer

Skylight is committed to building a diverse and inclusive team. All qualified applicants will be considered without regard to race, color, religion, sex, sexual orientation, gender identity or expression, age, national origin, disability, protected veteran status, or any other factor protected by applicable federal, state, or local laws. If you're the best person for the job, we want you on board!

We hire across the U.S., but for legal reasons, we have to list NY and CO separately.

For Colorado-based candidates, the range being offered for this role is $200-$220K based on experience and for California-based candidates, the range being offered for this role is $200-$220K based on experience. Pursuant to the San Francisco Fair Chance Ordinance, we will consider employment for qualified applicants with criminal histories in a manner consistent with the requirements of this law.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Skylight

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