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Skylight

Skylight

HomeSwipe is an iOS and Android app that enables users to find apartments for rent in New York City.

1-10 employees
Smart Home
Private Company
WebsiteLinkedInFacebookShareTweet
Smart HomeAppsReal Estate

Remote-First Company

This company operates with a remote-first culture, allowing team members to work from anywhere. Team members are distributed across the U.S. and Canada.

Open Positions12

United StatesFull-TimeTechnology StartupPosted
Director of Customer Service, Enablement and AI
  • Scale support capacity for company growth through AI and automation while making strategic build-vs-buy decisions.
  • Drive performance metrics including resolution, containment, and CSAT across chat, email, and voice channels.
  • Manage knowledge infrastructure by maintaining taxonomy, mining ticket logs, and preparing AI-ready content.
  • Partner with human support teams to roll out agentic tools, create feedback loops, and establish SOPs.
  • Enforce QA and engineering discipline by treating prompts like production code using test suites and staged rollouts.
  • Measure and report business ROI, cost per contact, and capacity optimization.
  • Execute as a player-coach to support the AI operations team while scaling the function.
Data AnalysisChange ManagementZendesk

$150-185k based on experience

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Showing 1 of 12 positions

About Skylight

Skylight builds technology that connects loved ones and simplifies family life. You'll work on consumer products like the Skylight Frame and the acclaimed Skylight Calendar. Our products serve millions of users, helping families organize schedules, share memories, and stay connected. Skylight is entirely bootstrapped and profitable, scaling to over $300M+ in annual revenue.

How We Work

Skylight fosters a remote-first environment, hiring across the U.S. and Canada. We operate with core principles of autonomy, rigor, and care, empowering you to own your work. You'll join a team that values open communication and shared responsibility, making meaningful impact daily. Decisions happen in open channels; collaboration is key.

Why Join Us

  • Shape products used by millions of families globally every day.
  • Work in a bootstrapped, profitable company with over $300M+ in annual revenue, free from external investor pressures.
  • Enjoy tremendous autonomy to direct your work and solve complex problems.
  • Collaborate with smart, hardworking individuals who care deeply about meaningful products.
  • Benefit from comprehensive benefits, including unlimited PTO and wellness budgets.

Benefits & Perks

  • Competitive Salary + Equity Package
  • 401K matching
  • Wellness, learning, and home-office budgets
  • Health, Dental & Vision Medical Plans
  • Unlimited PTO
  • Company holidays on the first Friday of every month (with some exceptions)
  • Loaned laptop and Skylight Calendar for customer support specialists
  • 64 hours of accrued sick time annually

Tech Stack

cmswidgetsserver

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