Sketchy

Compensation

Full Description

Position Summary Sketchy is building the future of clinical education through storytelling, scalable platforms, and applied AI. As a Senior Software Developer, Backend, you will help lead the technical direction of our most critical backend systems and AI-enabled services, guiding architecture decisions that balance speed, reliability, and long-term maintainability. You will serve as a 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, and is excited to ship real-world AI systems that directly impact how clinicians learn and practice. Sketchy is hiring remote employees in these select US states: California, Colorado, Florida, Illinois, Massachusetts, Michigan, New Jersey, New York, Pennsylvania, Texas, Utah, and Washington! You’ll thrive here if you: Turn ambiguity into clear plans, tradeoffs, and execution paths Care deeply about reliability, observability, and operational excellence Believe applied AI should be pragmatic, measurable, safe, and cost-aware Responsibilities: Lead the design and implementation of backend services and APIs for key product areas, balancing delivery speed with reliability, scalability, and maintainability. Partner with Product and Design to clarify requirements, propose solutions, estimate effort, and deliver milestones with clear success metrics. Build and operate applied AI features in production (e.g., LLM-backed workflows, evaluation/guardrails, retrieval patterns, experimentation, and monitoring) with a focus on quality, safety, and cost. Contribute to architecture decisions through RFCs/design docs, proposing pragmatic patterns for service boundaries, data models, async workflows, caching, and migrations. Write high-quality code and raise the bar through code reviews, pairing, and sharing best practices; mentor junior engineers as needed. Improve operational health for the systems you own: observability, performance tuning, reliability improvements, and on-call outcomes. Participate in an on-call rotation and help debug/resolve production issues; contribute to post-incident learnings and follow-ups. Break down product requirements into well-scoped tickets and workstreams, coordinating with teammates to deliver predictably. What We’re Looking For: 6–10+ years building and operating production backend systems (consumer and/or B2B SaaS), including scaling, reliability, and distributed systems exposure. Strong experience with AWS (EC2/Fargate/Lambda/Queues), Terraform (or comparable IaC), Redis, relational databases, and SQL (Postgres). Strong experience with JavaScript/Node.js, TypeScript, and NestJS (or comparable modern frameworks). Experience with Docker/containerization, CI/CD, and production deployment patterns. Proven ability to design and ship scalable systems, and to make sound tradeoffs across APIs, data modeling, async patterns, caching, and migrations. Strong instrumentation/observability skills (metrics/logging/tracing), performance debugging, and cost awareness (e.g., Datadog). Clear communicator who collaborates well with technical and non-technical partners. Comfortable in startup environments: ownership, pragmatism, and delivery under uncertainty Applied AI / Generative AI (Must Have) Practical 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. Nice to Have Experience 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). If 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. Who you will work closely with Vlad Iacob – Director of Engineering Ryan Pierce – Tech Lead, Frontend Jaimie Stein – Tech Lead, Data Salary Range $160,000 to $200,000 annual salary plus a performance-based annual bonus and stock options Our Perks 100% Individual Health Coverage - We got you covered! Equity - From day one, you’ll have a stake in our future growth. 401(k) - We support your financial future with up to 5% matching. Annual Company Retreat in Cool Places Flexible Time Off Annual Work Anniversary Stipend Monthly Wifi & Phone Reimbursement Short Term & Long Term Disability Sketchy 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.