Director of IT, Skylight
$200-220k
+ Equity Package
Digital picture frams and smart calendars
Be an early applicant
Digital picture frams and smart calendars
101-200 employees
Be an early applicant
$200-220k
+ Equity Package
101-200 employees
Company mission
To connect loved ones by creating the world's simplest products and services that improve family life.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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
Our take
Skylight, a digital photo frame and smart calendar brand, has emerged as a solution to a timeless problem: staying connected with loved ones in an increasingly digital world. With over 1.5M units sold, Skylight's flagship product, the Skylight Frame, has quickly become the top-selling digital picture frame on Amazon. It offers a way for users to share cherished photos with family and friends from anywhere in the world.
To further expand its reach, Skylight recently closed a successful funding round. This funding marks a pivotal moment for the company, affirming its journey from a decade of profitable bootstrapping to a new era of growth and innovation. The capital injection will be used to support the company's mission to meet the surging demand for its tech and propel it to even greater heights.
Steph
Company Specialist at Welcome to the Jungle
Insights
Company
Company benefits
- Ability to work remotely
- Health, Vision, and Dental Insurance
- 401k
- Monthly Health/Wellness Stipend
- Annual Learning/Self-Development Stipend
- Fun and collaborative culture
Company HQ
Central LA, Los Angeles, CA
Leadership
Michael Segal
(Co-Founder & CEO)Previously founded Curio Road where they served as CEO. They also worked as a Product Manager at Spotify.
Salary benchmarks
We don't have enough data yet to provide salary benchmarks for this role.
Submit your salary to help other candidates with crowdsourced salary estimates.
Share this job
View 8 more jobs at Skylight