Principal Software Engineer - AI

Job Summary

OnBoard, a leading board management software platform serving over 5,000 organizations worldwide, is seeking a Principal Software Engineer with a strong focus on AI to join our fully remote engineering team. This is a senior-level role that combines deep technical expertise in SaaS development with cutting-edge AI/ML integration, including semantic search, RAG frameworks, vector databases, and LLM orchestration. As a Principal Engineer, you will not only design and build next-generation, AI-powered agentic experiences but also provide technical leadership, mentorship, and strategic direction for long-range technology investments. You will work in a high-trust, high-autonomy environment where your decisions directly shape the platform used by boards and committees in higher education, healthcare, government, and enterprise sectors. If you are passionate about solving complex problems, championing AI-assisted development practices, and building scalable, maintainable applications, this role offers an exceptional opportunity to make a significant impact while working from anywhere in the US.

Key Responsibilities

• Lead the design, development, and implementation of complex software systems, including advanced AI-powered capabilities such as semantic search systems, vector databases, RAG-based architectures, and LLM orchestration patterns.
• Translate business requirements into well-formed technical designs and bring them to life iteratively with the team, ensuring alignment with business goals and user needs.
• Collaborate with cross-functional teams to define project goals, scope, and timelines, ensuring technical feasibility and resource optimization.
• Mentor and coach team members, fostering their professional growth and promoting a culture of knowledge sharing and continuous learning.
• Write reusable code, build libraries for future use, conduct thorough code reviews, enforce coding standards, and ensure high code quality across the codebase.
• Champion the adoption of AI-assisted development tools such as Claude Code, GitHub Copilot, and Codex to accelerate development velocity and improve code quality.
• Build golden pathways and developer experience tooling that scales engineering capability across the organization.
• Drive technical innovation and identify opportunities for process improvements, optimization, and adoption of emerging technologies.
• Champion architectural integrity while maintaining an iterative, gated delivery approach to balance speed and stability.
• Stay up to date with emerging technologies and industry trends, evaluating their potential impact on our software solutions.

Role Requirements & Qualifications

• Bachelor's Degree in software engineering, computer science, information technology, or commensurate experience.
• 10+ years of proven experience in SaaS development, primarily developing user-facing production features on a modern web stack.
• 5-7 years of experience developing web applications with C# and .NET Core.
• 5+ years of experience with RESTful design patterns and microservices architecture, including high-scale cloud mechanisms such as event hubs, messaging systems, and data lakes.
• 1+ years of experience with AI-powered development tools (Claude, GitHub Copilot, Cursor, or similar) with a demonstrated track record of leveraging AI assistants to accelerate development velocity and code quality.
• Experience in one or more AI/ML areas: semantic search, vector databases, RAG frameworks, LLM orchestration, prompt engineering, or AI tooling development.
• Excellent troubleshooting skills with the ability to analyze and resolve difficult problems quickly.
• Experience working in a high-transaction, high-security environment where SOC2 and ISO27001 compliance is required.
• Strong proficiency in CI/CD pipelines and git workflow, ideally in Azure DevOps.
• Mastery of agile development methodologies and DevOps practices.
• Demonstrated technical leadership experience in software development projects.

Skills Inventory

Essential skills:

• C# and .NET Core development
• RESTful API design and microservices architecture
• AI/ML integration (semantic search, RAG, vector databases, LLM orchestration)
• AI-assisted development tools (GitHub Copilot, Claude, Cursor)
• Cloud platforms (Azure preferred) and high-scale systems
• CI/CD pipelines and DevOps practices
• Agile methodologies
• Technical leadership and mentorship

Preferred skills:

• Experience with Azure DevOps
• Knowledge of SOC2 and ISO27001 compliance
• Experience with event hubs and messaging systems
• Prompt engineering and AI tooling development
• Developer experience tooling and golden pathways

Salary & Compensation Estimation

For a Principal Software Engineer with AI specialization and 10+ years of experience, the expected base salary range in the US is typically between $180,000 and $240,000 per year, depending on location, experience, and equity compensation. OnBoard offers a comprehensive benefits package including medical, dental, vision, 401K with company match, paid time off, and fully remote work with company-provided equipment. For candidates in Canada, Australia, or the UK, compensation is adjusted to local market rates, with additional perks such as superannuation, pension contributions, and private medical insurance.