{"schemaVersion":"jobsearcher.job.v1","id":"77184ce050c9f6ec8e24f1c4","url":"https://jobsearcher.com/jobs/77184ce050c9f6ec8e24f1c4","canonicalUrl":"https://jobsearcher.com/jobs/77184ce050c9f6ec8e24f1c4","title":"Principal Software Developer, Backend","description":"Our Company\nMedicine is evolving faster than ever, and so is the way clinicians learn. At Sketchy, we partner with institutions, health systems, and learners to expand access to high-quality clinical education that prepares clinicians for what’s next.\n\nOur mission is to help clinicians build the readiness and agility needed to deliver better decisions, stronger patient connections, and higher-quality care in a world shaped by AI and precision medicine.\n\nWe’re reimagining how clinical reasoning, communication, and other core competencies are developed, empowering every learner to adapt, grow, and lead in the future of healthcare.\n\nPosition Summary\nSketchy is building the future of clinical education through storytelling, scalable platforms, and applied AI. As a Principal Software Developer, Backend, you will own the technical direction of our most critical backend systems and AI-enabled services, guiding architecture decisions that balance speed, reliability, and long-term maintainability.\n\nYou will serve as a technical leader across teams, partnering closely with Product, Design, Data, and Frontend Engineering to turn ambiguous product goals into robust, production-ready systems. This role is ideal for an experienced backend engineer who thrives in high-ownership environments, enjoys mentoring others, and is excited to ship real-world AI systems that directly impact how clinicians learn and practice.\n\nSketchy is hiring remote employees in these select US states: California, Colorado, Florida, Illinois, Massachusetts, Michigan, New Jersey, New York, Pennsylvania, Texas, Utah, and Washington!\n\nYou’ll thrive here if you:\nEnjoy owning architecture and technical strategy, not just implementation\nTurn ambiguity into clear plans, tradeoffs, and execution paths\nCare deeply about reliability, observability, and operational excellence\nBelieve applied AI should be pragmatic, measurable, safe, and cost-aware\nRaise the bar for engineering quality through mentorship and example\nResponsibilities:\nOwn architecture and technical direction for major backend systems and initiatives, balancing product velocity with reliability, scalability, and long-term maintainability.\nLead cross-functional delivery with Product Managers and Designers by translating ambiguous problems into clear technical plans, milestones, and measurable outcomes.\nDesign, build, and operate applied AI systems in production, including:\nLLM-backed workflows and services\nRetrieval patterns (RAG), embeddings, and vector stores\nEvaluation frameworks, guardrails, and quality measurement\nMonitoring for latency, cost, failures, and model drift\nEstablish and uphold engineering best practices across the backend organization, including code quality, testing strategy, documentation, operational readiness, and incident response.\nAct as a force multiplier through technical mentorship, pairing, architecture reviews, and raising standards across the engineering team.\nDrive operational excellence by improving observability, performance tuning, cost efficiency, system reliability, and on-call outcomes.\nParticipate in an on-call rotation to support production systems and lead investigations when issues occur.\nBreak down complex product requirements into well-scoped workstreams that enable predictable execution and high-quality delivery.\nWhat We’re Looking For:\n10+ years of experience building and operating production backend systems in consumer and/or B2B SaaS environments, including scaling and distributed systems.\nDeep expertise in AWS and cloud-native architectures (EC2, Fargate, Lambda, queues) with Infrastructure as Code (Terraform).\nStrong experience with Node.js, TypeScript, and modern backend frameworks (NestJS or equivalent).\nExperience with Redis, Postgres, SQL, and data-intensive backend systems.\nProven ability to design scalable architectures and lead complex technical decisions across APIs, data models, async workflows, caching, and migrations.\nStrong experience with Docker, CI/CD pipelines, and production deployment patterns.\nExpertise in observability, reliability, and cost optimization (metrics, logging, tracing; e.g., Datadog).\nExcellent communication skills and a strong record of ownership and delivery in fast-moving startup environments.\nApplied AI / Generative AI (Must Have)\nHands-on experience shipping AI-enabled features into production, including LLM-backed workflows, retrieval patterns (RAG, embeddings, vector databases), evaluation and guardrails, and monitoring for quality, latency, cost, and model drift.\nNice to Have\nExperience building internal platforms or developer tooling; background in edtech or learning analytics; familiarity with modern privacy and security best practices (PII handling, least privilege, secure-by-default).\n\nIf you don’t have 100% of the bullets listed above, that’s okay! We know there are no perfect applicants. If you are passionate about making a meaningful difference, we want to hear from you! Learn more about Sketchy’s culture at sketchy.com/careers.\n\nWho you will work closely with\nVlad Iacob – Director of Engineering\nRyan Pierce – Tech Lead, Frontend\nJaimie Stein – Tech Lead, Data\n\nSalary Range\n$195,000 to $215,000 annual salary plus a performance-based annual bonus and stock options\n\nOur Perks\n100% Individual Health Coverage - We got you covered!\nEquity - From day one, you’ll have a stake in our future growth.\n401(k) - We support your financial future with up to 5% matching.\nAnnual Company Retreat in Cool Places\nFlexible Time Off\nAnnual Work Anniversary Stipend\nMonthly Wifi & Phone Reimbursement\nShort Term & Long Term Disability\nSketchy Group LLC is an Equal Opportunity Employer. All applicants will receive consideration without discrimination on the basis of race, religion, color, sex, age, sexual orientation, marital status, national origin, disability or any other basis prohibited by applicable law.\n\nThe pay range for this role is:\n195,000 - 215,000 USD per year(Remote (United States))","company":"Sketchy","rawCompany":"sketchy","city":"Remote","state":"OR","isRemote":false,"isActive":false,"createdAt":"2026-04-14T10:43:58.875Z","occupations":[{"code":"15-1252.00","title":"Software Developers","slug":"software-developers"},{"code":"15-1299.08","title":"Computer Systems Engineers/Architects","slug":"computer-systems-engineers-architects"},{"code":"15-1254.00","title":"Web Developers","slug":"web-developers"}],"industries":[{"code":"541512","title":"Computer Systems Design Services","slug":"computer-systems-design-services"},{"code":"513210","title":"Software Publishers","slug":"software-publishers"},{"code":"541511","title":"Custom Computer Programming Services","slug":"custom-computer-programming-services"}],"jobPosting":{"@context":"https://schema.org","@type":"JobPosting","title":"Principal Software Developer, Backend","description":"Our Company\nMedicine is evolving faster than ever, and so is the way clinicians learn. At Sketchy, we partner with institutions, health systems, and learners to expand access to high-quality clinical education that prepares clinicians for what’s next.\n\nOur mission is to help clinicians build the readiness and agility needed to deliver better decisions, stronger patient connections, and higher-quality care in a world shaped by AI and precision medicine.\n\nWe’re reimagining how clinical reasoning, communication, and other core competencies are developed, empowering every learner to adapt, grow, and lead in the future of healthcare.\n\nPosition Summary\nSketchy is building the future of clinical education through storytelling, scalable platforms, and applied AI. As a Principal Software Developer, Backend, you will own the technical direction of our most critical backend systems and AI-enabled services, guiding architecture decisions that balance speed, reliability, and long-term maintainability.\n\nYou will serve as a technical leader across teams, partnering closely with Product, Design, Data, and Frontend Engineering to turn ambiguous product goals into robust, production-ready systems. This role is ideal for an experienced backend engineer who thrives in high-ownership environments, enjoys mentoring others, and is excited to ship real-world AI systems that directly impact how clinicians learn and practice.\n\nSketchy is hiring remote employees in these select US states: California, Colorado, Florida, Illinois, Massachusetts, Michigan, New Jersey, New York, Pennsylvania, Texas, Utah, and Washington!\n\nYou’ll thrive here if you:\nEnjoy owning architecture and technical strategy, not just implementation\nTurn ambiguity into clear plans, tradeoffs, and execution paths\nCare deeply about reliability, observability, and operational excellence\nBelieve applied AI should be pragmatic, measurable, safe, and cost-aware\nRaise the bar for engineering quality through mentorship and example\nResponsibilities:\nOwn architecture and technical direction for major backend systems and initiatives, balancing product velocity with reliability, scalability, and long-term maintainability.\nLead cross-functional delivery with Product Managers and Designers by translating ambiguous problems into clear technical plans, milestones, and measurable outcomes.\nDesign, build, and operate applied AI systems in production, including:\nLLM-backed workflows and services\nRetrieval patterns (RAG), embeddings, and vector stores\nEvaluation frameworks, guardrails, and quality measurement\nMonitoring for latency, cost, failures, and model drift\nEstablish and uphold engineering best practices across the backend organization, including code quality, testing strategy, documentation, operational readiness, and incident response.\nAct as a force multiplier through technical mentorship, pairing, architecture reviews, and raising standards across the engineering team.\nDrive operational excellence by improving observability, performance tuning, cost efficiency, system reliability, and on-call outcomes.\nParticipate in an on-call rotation to support production systems and lead investigations when issues occur.\nBreak down complex product requirements into well-scoped workstreams that enable predictable execution and high-quality delivery.\nWhat We’re Looking For:\n10+ years of experience building and operating production backend systems in consumer and/or B2B SaaS environments, including scaling and distributed systems.\nDeep expertise in AWS and cloud-native architectures (EC2, Fargate, Lambda, queues) with Infrastructure as Code (Terraform).\nStrong experience with Node.js, TypeScript, and modern backend frameworks (NestJS or equivalent).\nExperience with Redis, Postgres, SQL, and data-intensive backend systems.\nProven ability to design scalable architectures and lead complex technical decisions across APIs, data models, async workflows, caching, and migrations.\nStrong experience with Docker, CI/CD pipelines, and production deployment patterns.\nExpertise in observability, reliability, and cost optimization (metrics, logging, tracing; e.g., Datadog).\nExcellent communication skills and a strong record of ownership and delivery in fast-moving startup environments.\nApplied AI / Generative AI (Must Have)\nHands-on experience shipping AI-enabled features into production, including LLM-backed workflows, retrieval patterns (RAG, embeddings, vector databases), evaluation and guardrails, and monitoring for quality, latency, cost, and model drift.\nNice to Have\nExperience building internal platforms or developer tooling; background in edtech or learning analytics; familiarity with modern privacy and security best practices (PII handling, least privilege, secure-by-default).\n\nIf you don’t have 100% of the bullets listed above, that’s okay! We know there are no perfect applicants. If you are passionate about making a meaningful difference, we want to hear from you! Learn more about Sketchy’s culture at sketchy.com/careers.\n\nWho you will work closely with\nVlad Iacob – Director of Engineering\nRyan Pierce – Tech Lead, Frontend\nJaimie Stein – Tech Lead, Data\n\nSalary Range\n$195,000 to $215,000 annual salary plus a performance-based annual bonus and stock options\n\nOur Perks\n100% Individual Health Coverage - We got you covered!\nEquity - From day one, you’ll have a stake in our future growth.\n401(k) - We support your financial future with up to 5% matching.\nAnnual Company Retreat in Cool Places\nFlexible Time Off\nAnnual Work Anniversary Stipend\nMonthly Wifi & Phone Reimbursement\nShort Term & Long Term Disability\nSketchy Group LLC is an Equal Opportunity Employer. All applicants will receive consideration without discrimination on the basis of race, religion, color, sex, age, sexual orientation, marital status, national origin, disability or any other basis prohibited by applicable law.\n\nThe pay range for this role is:\n195,000 - 215,000 USD per year(Remote (United States))","datePosted":"2026-04-14T10:43:58.875Z","dateModified":"2026-04-14T10:43:58.875Z","hiringOrganization":{"@type":"Organization","name":"Sketchy","sameAs":"https://jobsearcher.com"},"jobLocation":{"@type":"Place","address":{"@type":"PostalAddress","addressLocality":"Remote","addressRegion":"OR","addressCountry":"US"}},"identifier":{"@type":"PropertyValue","name":"JobSearcher","value":"77184ce050c9f6ec8e24f1c4"},"url":"https://jobsearcher.com/jobs/77184ce050c9f6ec8e24f1c4"}}