About the job
Skylight builds digital products designed to help families stay connected. The Skylight Calendar, now in millions of homes, has earned praise from publications like Wired and the Wirecutter. The team recently introduced Calendar 2, which has received strong reviews.
Founded by former venture capitalists and serial entrepreneurs, Skylight has grown to over $300 million in annual revenue. The company is profitable, fully bootstrapped, and operates without outside investor pressure. This independence allows a focus on building products that genuinely improve family life.
Skylight values people who want to make a difference with thoughtful, practical technology. Those who care about supporting families and parents may find a meaningful place here.
Role overview
The Director of IT will establish and lead all IT functions at Skylight. As the first person in this position, responsibilities cover a wide range: employee onboarding, vendor management, daily technical support, and designing systems to improve company operations. Reporting to the VP of Engineering, this role collaborates closely with the Head of Security and the Head of People & Culture.
This is a hands-on position. The Director of IT will troubleshoot issues directly while also building infrastructure to reduce future problems.
What to know before applying
- Skylight operates in a less regulated environment. Compliance is voluntary beyond PCI SAQ-A, with a focus on practical data protection.
- Autonomy and ownership are core values. The Director of IT will shape strategy and work independently, without micromanagement.
- AI and automation are used to improve operations. Identifying and implementing new tools or automated processes is encouraged and supported.
Location
This position is based in Seattle, Washington.
