Ruby On Rails Jobs in Kentucky (NOW HIRING)

At Koala Health, we have our eyes set on an ambitious goal: to make managing your pets' health simple and delightful. We've already launched our pharmacy service that allows people to shop for their pets' medications and supplements online and get them delivered to their doorstep in presorted medication pouches. Now we're focused on continuing to improve that experience while building a suite of new products and services that will make the pet health experience even better. We are hiring a Principal Software Engineer to serve as a technical leader across the engineering organization. This is a highly hands-on role for an experienced engineer who enjoys building production systems while also influencing architecture, engineering standards, developer productivity, and the adoption of AI throughout the software development lifecycle. You will work closely with engineering, product, operations, and company leadership to identify opportunities, define technical direction, and drive execution on initiatives that have company-wide impact. Success in this role means:

• Architecting systems that scale with the business.
• Raising engineering quality and operational excellence.
• Accelerating development velocity through effective use of AI.
• Establishing best practices for AI-assisted and agentic software development.
• Mentoring engineers and helping the team make better technical decisions.
• Leveraging technology to simplify complex operational workflows and improve customer experiences.

• 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.

• 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.

We believe AI is transforming both software development and business operations. We're looking for an engineer who wants to help shape that transformation while remaining deeply hands-on. This role offers the opportunity to architect critical systems, influence engineering culture, establish AI-first development practices, and help build the technology foundation for the next stage of Koala's growth.

If you're excited about combining strong engineering fundamentals, practical AI expertise, and meaningful business impact, we'd love to talk.

• Meaningful mission helping modernize pet health
• Remote-first culture built on flexibility and trust
• Competitive base salary with performance-based incentives
• Medical, dental, and vision insurance with partial dependent coverage
• Generous PTO and a 401(k) plan
• Supportive, close-knit team that celebrates wins and learns fast

$150,000 - $160,000 a year

The target base salary range for this role isdependent on experience, skills, qualifications, and geographic location. In addition to base salary, this role is eligible for a comprehensive benefits package, including medical, dental, vision, 401(k), paid time off, and other company-sponsored benefits.

Koala Health is proud to be an Equal Employment Opportunity and Affimative Action employer. We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.