Skylight

Engineer software products using lean-agile principles and API-first design, analyze systems to reduce technical debt, and communicate tradeoffs to stakeholders. | U.S. citizenship, clean and secure code writing, strong data engineering and system reliability experience, with preferred skills in accessibility, infrastructure as code, and regulated environments. | About the job Skylight is a digital consultancy using design and technology to help government agencies deliver better public services. We’re at the forefront of a civic movement to reinvent how all levels of government serve families, patients, and many others in today’s digital world. If you want to play a part in driving this critical movement forward, we’d love for you to join our growing team of public interest technologists. The work we do matters. What you’ll do Engineer a software product as part of a cross-functional team, which includes user experience researchers and designers, product managers, engineers, and other functional specialists Achieve technical excellence by advocating for and adhering to lean-agile engineering principles and practices such as API-first design, simple design, continuous integration, version control, and automated testing Select and use the right tools, frameworks, languages, and technologies for the job, with a preference for open-source solutions Analyze systems to identify technical debt, instability, unreliability, and other opportunities for improvement, then design, document, and communicate solutions What we’re looking for Basic qualifications Write clean, working, and reusable code, backed by automated tests Build secure, compliant software and defend against common vulnerabilities Understand the fundamentals of data engineering, including how to use different datastores to handle persistent data in software systems Understand how the pieces of a software system fit together, and design with performance, reliability, and availability in mind Put users at the center of your work, thinking through the impact and implications of the code you write Work directly with stakeholders to understand their needs, explain technical tradeoffs in plain language, and shape what gets built. Nice-to-haves Experience building accessible software that meets Section 508 and WCAG standards Experience working in constrained or regulated environments, such as legacy systems, ATO boundaries, or FedRAMP-authorized cloud services Experience with infrastructure as code (e.g., Terraform) and/or immutable infrastructure (e.g., Docker) Experience contributing to open-source projects or building software in the open Other requirements You must be a U.S. Citizen to be eligible for employment All work must be conducted within the U.S., excluding U.S. territories As a government contractor, you may be required to obtain a public trust or security clearance, up to Top Secret You will be required to complete a company background check successfully. Some of our available roles are on federal contracts that require a degree or additional years of experience as a substitute Ability to travel, as needed Location This is a fully remote position. Care package Salary We want to give you the most competitive salary possible. After all, you deserve it! To that end, we use the results of our interview process to determine what salary is most appropriate given your current level of seniority. For a Software Engineer at Skylight, the current salary ranges are as follows: Associate Software Engineer : $90,000–$125,000 Software Engineer I: $120,000–$140,000 Software Engineer II: $135,000–$160,000 Senior Software Engineer: $150,000–$185,000 Staff Software Engineer: $170,000–$203,000 Principal Software Engineer: $180,000–$230,000 Benefits Your well-being is important to us, so we focus on supporting you in a variety of ways: Medical insurance, dental insurance, vision insurance Short-term and long-term disability insurance Life and AD&D insurance Dependent care FSA, healthcare FSA, health savings account Dollar-for-dollar 401(k) match up to 10% of your salary with no vesting period Flexible paid-time-off policy (generally around 25 days per year), plus 11 paid federal holidays Up to 12 weeks paid-time-off for all eligible new birth, adoption, or foster parents Performance rewards, including annual salary increase, annual performance bonus, spot bonuses, and stock options Business development / sales bonuses Referral bonuses Annual $2,000 allowance for professional development Annual $750 allowance for tech-related purchases Annual swag budget of $100 to display your Skylight pride with some merchandise (hoodies, hats, and more) Flexible, remote-friendly work environment An environment that empowers you to unleash your superpowers for public good Interview tips We want you to have a great interview experience with us! Here are some tips to help you prepare for a successful interview: Visit our join page to learn more about how our interview process works. Check out our Career Pathways framework to learn more about the different roles within Skylight and the skills needed to do them. If you’d like to request reasonable accommodations during the application or interviewing process, please contact our recruiting team at recruiting@skylight.digital. We participate in E-Verify and upon hire, will provide the federal government with your Form I-9 information to confirm that you’re authorized to work in the U.S. We are an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, national origin, sex, religion, age, disability, veteran status, or any other category protected by applicable law.

Build and iterate on experiments across e-commerce platforms to improve subscription rates and retention while collaborating cross-functionally. | 5+ years experience with TypeScript and React including React Native or modern e-commerce stacks, strong understanding of A/B testing and growth outcomes. | 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 building a brand new Growth Pod at Skylight, and this is one of its founding engineering roles. You’ll be joining a small, focused team with a clear mandate: improve the metrics that power this business. That means subscription attach rate above all else, but also retention, and related growth goals across our product surfaces. In the near term, you’ll spend most of your time in our Shopify + Hydrogen e-commerce website, building and iterating and running experiments. Over time, we expect the work to shift: roughly 70% in our React Native mobile and web app, 30% in the e-comm site. This is a role that will grow and evolve as the Pod does. Our ideal candidate is a versatile frontend engineer with deep experience in Typescript and React and/or React Native, who is equally comfortable reasoning about business outcomes as they are writing clean, well-tested code. You care deeply about how your work moves the needle, not just whether it shipped. And you bring rigor to experimentation: designing tests carefully, interpreting results honestly, and building experiences that real families will encounter every day. Your title and compensation will be determined by your experience and expertise. Our bottom-line requirements are a strong foundation in Typescript, React, A/B testing, and analytics along with a genuine interest in growth and experimentation, and a drive to deliver outcomes that matter to the business. Responsibilities Build, launch, and iterate on experiments across our e-commerce site and mobile/web app to improve subscription attach rate, retention, and other growth metrics. Implement new features and UI flows in our Shopify + Hydrogen e-comm site and our React Native app with a high bar for quality and user experience. Help evaluate, implement, and configure the A/B testing and experimentation tools the Growth Pod adopts. Collaborate closely with product managers, designers, and growth-focused cross-functional partners to move quickly from hypothesis to live test. Write high-quality, reusable, and maintainable code, and contribute to a comprehensive test suite to ensure stability as we ship fast. Participate in code reviews and bring constructive, thoughtful feedback to elevate the team’s work. Help establish processes for monitoring performance and tracking experiment results and health metrics. Extensive experience (5+ years) with Typescript and React, with meaningful production work in React Native and/or a modern e-commerce frontend stack. Experience with Shopify (and especially with Hydrogen) would be amazing. Genuine interest in growth engineering. You want to understand why users convert (or don’t), and you care about the business outcomes your code produces. Comfort with A/B testing concepts and a respect for statistical rigor. You know the difference between a result and a fluke. Strong understanding of frontend architecture and design patterns, with a high bar for code quality and user experience. Excellent cross-functional communication skills. You can work fluidly with Product, Design, and Data, and you’re comfortable operating with autonomy on a small, scrappy team. 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 $ 180-220K based on experience and for California-based candidates, the range being offered for this role is $ 180-220K 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.

Design and launch new AI features integrating LLMs using Ruby on Rails, own product initiatives, collaborate cross-functionally, and mentor engineers. | 6+ years in software product development with deep Ruby on Rails or similar backend mastery, experience shipping zero-to-one products, and working with LLM providers. | 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. The Role 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. What You'll Do 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 Nice to Haves 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) 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 $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.

Design and launch AI features integrating LLMs into backend platform using Ruby on Rails. | 6+ years backend experience with Ruby on Rails or similar, experience shipping zero-to-one products and working with LLM providers. | 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. The Role 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. What You'll Do 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 Nice to Haves 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) 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 $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.