Edtech.com's Summary

Sketchy is hiring a Principal Software Developer, Backend to lead the technical direction of critical backend systems and AI-enabled services. The role requires designing, building, and operating scalable backend infrastructures and applied AI features while collaborating closely with cross-functional teams to deliver production-ready systems that enhance clinical education.

Highlights

Own architecture and technical direction for major backend systems balancing speed, reliability, and maintainability.
Lead cross-functional delivery involving Product Managers, Designers, Data, and Frontend Engineering.
Design and operate AI systems including LLM-backed workflows, retrieval patterns (RAG), embeddings, and model monitoring.
Establish and uphold engineering best practices around code quality, testing, documentation, and incident response.
Mentor engineers and lead architecture reviews to elevate engineering standards.
Experience required: 10+ years in backend development with expertise in Node.js, TypeScript, AWS (EC2, Fargate, Lambda), Terraform, Redis, Postgres, and observability tools like Datadog.
Must have hands-on experience shipping AI-enabled production features involving generative AI, vector stores, and evaluation frameworks.
Participate in on-call rotations and incident management to ensure system reliability.
Compensation ranges from $195,000 to $215,000 annually plus performance bonuses and stock options.
Work closely with Engineering leadership and tech leads across frontend and data teams.

Principal Software Developer, Backend Full Description

Principal Software Developer, Backend

Our Company

Medicine 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.

Our 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.

We’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.

Position Summary

Sketchy 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.

You 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.

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:

Enjoy owning architecture and technical strategy, not just implementation
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
Raise the bar for engineering quality through mentorship and example

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.

What We’re Looking For:

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.

Applied AI / Generative AI (Must Have)

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.

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

$195,000 to $215,000 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.

The pay range for this role is:

195,000 - 215,000 USD per year (Remote (United States))

Original Job Description

Principal Software Developer, Backend

Our Company

We’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.

Position Summary

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:

Enjoy owning architecture and technical strategy, not just implementation
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
Raise the bar for engineering quality through mentorship and example

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.

What We’re Looking For:

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.

Applied AI / Generative AI (Must Have)

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.

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).

Who you will work closely with

Vlad Iacob – Director of Engineering

Ryan Pierce – Tech Lead, Frontend

Jaimie Stein – Tech Lead, Data

Salary Range

$195,000 to $215,000 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

The pay range for this role is:

195,000 - 215,000 USD per year (Remote (United States))

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