Apply on Employer Site

Sketchy · 1 day ago

Principal Software Developer, Backend

United States

Full-time

Remote

Lead/Staff

$195K/yr - $215K/yr

10+ years exp

Sketchy is a company that partners with institutions and health systems to enhance clinical education. They are seeking a Principal Software Developer, Backend to lead the technical direction of backend systems and AI-enabled services, ensuring reliability and scalability while mentoring other engineers.

E-LearningEducationPersonal Development

Responsibilities

Own architecture and technical direction for major backend systems and initiatives, balancing product velocity with reliability, scalability, and long-term maintainability

Lead cross-functional delivery with Product Managers and Designers by translating ambiguous problems into clear technical plans, milestones, and measurable outcomes

Design, build, and operate applied AI systems in production, including:

LLM-backed workflows and services

Retrieval patterns (RAG), embeddings, and vector stores

Evaluation frameworks, guardrails, and quality measurement

Monitoring for latency, cost, failures, and model drift

Establish and uphold engineering best practices across the backend organization, including code quality, testing strategy, documentation, operational readiness, and incident response

Act as a force multiplier through technical mentorship, pairing, architecture reviews, and raising standards across the engineering team

Drive operational excellence by improving observability, performance tuning, cost efficiency, system reliability, and on-call outcomes

Participate in an on-call rotation to support production systems and lead investigations when issues occur

Break down complex product requirements into well-scoped workstreams that enable predictable execution and high-quality delivery

Qualification

AWSNode.jsTypeScriptApplied AIDockerCI/CD pipelinesPostgresRedisInfrastructure as CodeOperational excellenceCommunicationMentorship

Required

10+ years of experience building and operating production backend systems in consumer and/or B2B SaaS environments, including scaling and distributed systems

Deep expertise in AWS and cloud-native architectures (EC2, Fargate, Lambda, queues) with Infrastructure as Code (Terraform)

Strong experience with Node.js, TypeScript, and modern backend frameworks (NestJS or equivalent)

Experience with Redis, Postgres, SQL, and data-intensive backend systems

Proven ability to design scalable architectures and lead complex technical decisions across APIs, data models, async workflows, caching, and migrations

Strong experience with Docker, CI/CD pipelines, and production deployment patterns

Expertise in observability, reliability, and cost optimization (metrics, logging, tracing; e.g., Datadog)

Excellent communication skills and a strong record of ownership and delivery in fast-moving startup environments

Hands-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

Preferred

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)