Principal Software Engineer, AI & Platform

Koala Health is hiring a Principal Software Engineer to provide hands-on technical leadership across its engineering organization. The role shapes architecture and engineering standards, advances AI-assisted and agentic development, and leads cross-functional initiatives to build scalable systems and improve customer and operational experiences.

Responsibilities:

• Define and evolve architectural standards across customer-facing and operational systems
• Lead the design of complex software systems, integrations, workflows, and data models
• Drive long-term technical strategy while balancing short-term business priorities
• Identify technical risks and opportunities early and develop pragmatic plans to address them
• Lead architectural reviews and guide major technical decisions across teams
• Establish patterns that improve reliability, maintainability, scalability, and developer productivity
• Champion AI-assisted software development across the organization
• Define best practices for leveraging LLMs in coding, testing, debugging, documentation, code review, and operational workflows
• Design and build agentic systems that automate engineering and business processes
• Evaluate emerging AI technologies and determine where they can create measurable value
• Help iterate on Koala's approach to AI-enabled software development and organizational productivity
• Ensure AI systems are implemented responsibly, securely, and with appropriate operational safeguards
• Raise the bar for code quality, testing, documentation, and operational readiness
• Drive improvements in CI/CD, deployment safety, developer experience, and engineering workflows
• Establish standards for observability, monitoring, alerting, and incident response
• Introduce tooling and automation that improve engineering velocity without sacrificing quality
• Foster a culture of ownership, continuous improvement, and technical excellence
• Partner closely with Product, Operations, Pharmacy, Customer Care, Growth, and Finance teams to understand business challenges and design effective solutions
• Translate ambiguous business requirements into scalable technical approaches
• Lead initiatives from concept through implementation, rollout, and operational support
• Ensure technical decisions align with company goals and customer outcomes
• Help mentor engineers across all experience levels
• Provide thoughtful guidance through design reviews, architecture discussions, and code reviews
• Help develop engineering processes that scale as the organization grows
• Serve as a trusted technical advisor to cross-functional stakeholders
• Influence engineering culture through technical leadership rather than organizational authority

Requirements:

• Bachelor's degree or equivalent
• 10+ years of professional software engineering experience building and operating complex, production-scale systems
• Expert-level Ruby on Rails experience with strong knowledge of modern web application architecture, distributed systems, APIs, data modeling, and cloud platforms (AWS, GCP, or Azure)
• Proven experience leading technical architecture, driving engineering direction, mentoring engineers, and delivering reliable, observable, high-performing systems
• Strong product and business judgment with excellent written and verbal communication skills
• Deep expertise with modern AI development, including LLMs, AI-assisted coding tools (e.g., Claude, Codex, GitHub Copilot), and building AI-powered products, agents, automation, or developer workflows
• Understanding of agent architectures, retrieval systems, tool-calling, evaluation frameworks, and AI system reliability, with a demonstrated ability to use AI to improve engineering velocity and team effectiveness
• Authorization to work in the United States (Koala is not able to sponsor visas for this role)
• Experience in healthcare, pharmacy, veterinary, or other regulated industries
• Experience in high-volume eCommerce, subscription businesses, logistics, or operations-heavy environments
• Experience with event-driven architectures, workflow orchestration systems, and asynchronous processing
• Experience leading platform engineering, infrastructure, or developer productivity initiatives
• Familiarity with AI evaluation, observability, governance, and operational best practices