Hourly 1099 Software Developer Contractor Jobs in Rutland, VT

We're building a world of health around every individual - shaping a more connected, convenient and compassionate health experience. At CVS Health, you'll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselvesaccountable and prioritize safety and quality in everything we do. Join us and be part of something bigger - helping to simplify health care one person, one family and one community at a time.

Position Summary
We're looking for a Lead Director of Software Engineering who thinks like a founder, executes like a principal engineer, and leads like someone who's done it at the highest levels of the industry. You will set the bar - and then raise it.

What You'll Actually Do

• Drive technical strategy across a multi-team engineering organization (50-150+ engineers), setting architectural standards, defining engineering excellence benchmarks, and personally reviewing and elevating the work.
• Operational Efficiency. Every system design decision you make should start with the question: How to create10x leverage? You will actively embed LLMs, generative AI, agentic workflows, and ML-powered automation into the engineering lifecycle, not just as experiments, but as production-grade differentiators.
• Own delivery at velocity. You ship. You are accountable for outcomes, not roadmaps. You hold your teams to the same standard.
• Partner at the executive level - with Product owners, Data Engineers, and Health care business leaders - translating business strategy into engineering bets with precision and conviction.
• Be the technical voice in the room You call out architectural debt, push back on infeasible timelines, and advocate for the right engineering investment.

Required Qualifications

• 10+ years of progressive software engineering experience, including 5+ years leading large-scale engineering organizations. You have built and scaled systems that serve tens of thousands of users. You know what happens when your system goes down.
• Deep, hands-on technical foundation in distributed systems, cloud-native architectures, and modern backend engineering at scale.
• Proven AI platform ownership. You have deployed production AI systems - not POCs, not demos, not limited to prompt engineering. You understand model deployment pipelines, vector databases, RAG architectures, LLM orchestration, inference optimization, and responsible AI principles.
• Track record of engineering transformation. You have migrated monoliths to microservices, modernized legacy platforms under real business pressure, and lived the consequences of every architectural decision you've made.

Preferred Qualifications

• Healthcare or highly regulated domain experience - You have navigated HIPAA, CMS compliance, PHI data handling development.
• Platform engineering ownership - You have built or led internal developer platforms, engineering productivity tooling.

Education

Minimum

• Bachelor's degree in Computer Science, Software Engineering, Mathematics, or a closely related technical discipline - or equivalent demonstrated engineering depth through work history, open source portfolio, or verifiable technical contribution at scale.

Preferred

• Master's degree (M.S. or M.Eng.) in Computer Science, Artificial Intelligence, Machine Learning, Data Science, or a related quantitative field. Graduate-level training in algorithms, distributed systems, statistical learning, or systems design gives us confidence in your technical ceiling.

Pay Range

The typical pay range for this role is:

$144,200.00 - $288,400.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company's equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This fulltime position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial wellbeing of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 07/06/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.