Senior or Staff Backend Engineer, AI Features

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 Buddy, 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.

Our ideal candidate is a seasoned backend engineer with experience building AI-powered systems (tool calls, evals, etc.) and a passion for creating products and features that really matter to customers. You know how to work with LLM APIs, optimize backend infrastructure, and work closely with not only engineers from other stacks, but also cross-functional partners, from retail to customer support to data. We're looking for someone who loves finding simple, straightforward technical solutions to complex problems.

We're looking for a seasoned Back End Software Engineer (Senior or Staff level) to work directly with our GM of New Businesses to build out new AI-powered features across our platform. You'll work primarily in Ruby on Rails to bring brand new products and features to life by integrating with LLMs from vendors like OpenAI, Google, etc.

• Design, build, and launch new user-facing features powered by large language models (LLMs)
• Own major product initiatives from zero-to-one, in partnership with a small but mighty team
• Collaborate deeply with Product and Design to shape new products and features
• Integrate with third-party APIs like OpenAI, Google, etc., and explore new model capabilities
• Contribute to our codebases in Ruby on Rails
• Write maintainable, high-quality code with strong test coverage
• Mentor other engineers through code reviews and design discussions

• 6+ years experience building software products end to end
• Deep mastery of either Ruby on Rails or another similar back end language
• Demonstrated ability to ship zero-to-one products as a solo engineer or team lead
• Experience with OpenAI, Anthropic, or similar LLM providers
• Clear communication and collaboration skills across disciplines
• Startup experience strongly preferred

• Familiarity with prompt engineering or retrieval-augmented generation (RAG)
• Prior work on family-facing or consumer social products

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)

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 $180-$240K based on experience and for California-based candidates, the range being offered for this role is $180-$240K 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.