[Hiring] Principal Software Engineer @OnBoard

Role Description

The Principal Software Engineer will play a critical role in designing, developing, and implementing high-quality software solutions. This position is responsible for the development of next-generation SaaS applications - including AI-powered and agentic experiences - as well as providing technical leadership for long-range investments and planning. The Principal Software Engineer has a passion for building maintainable, scalable, and beautiful applications, with heavy emphasis on optimizing user experience, solving problems, and delighting customers and business stakeholders. The Principal Software Engineer must be able to break down complex problems and design elegant, easy-to-maintain solutions that are resilient and robust. Additionally, this role provides technical leadership, mentorship, and guidance to the engineering team, while driving innovation in AI-assisted development practices and ensuring established best practices are followed.

Critically, this role involves AI/ML integration including:

• Semantic search
• RAG (Retrieval-Augmented Generation) frameworks
• Vector database architectures
• LLM operations
• Orchestration patterns
• AI tooling integration

We recognize that exceptional engineers may have depth in some areas and breadth in others - experience across these areas is strongly desired but not required. We value engineers who have experience learning and leading the adoption of emerging technologies.

Qualifications

• Bachelor's Degree in software engineering, computer science, information technology, or commensurate experience.
• 10+ years proven experience in SaaS development, primarily developing user-facing production features on a modern web stack.
• 5-7 years' experience developing web applications with C# and .NET Core.
• 5+ years' experience with RESTful design patterns and microservices architecture; including high-scale cloud mechanisms like event hubs, messaging systems, and data lakes.
• 1+ years’ experience with AI-powered development tools (Claude, GitHub Copilot, Cursor, or similar) with demonstrated track record of leveraging AI assistants to accelerate development velocity and code quality.
• Experienced 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, ISO27001 compliance is required.
• Strong proficiency in CI/CD pipelines, git workflow, etc.; ideally in Azure DevOps.
• Mastery of agile development methodologies and DevOps practices.
• Demonstrated technical leadership experience in software development projects.

Requirements

• Lead the design, development, and implementation of complex software systems and solutions including advanced AI-powered capabilities such as semantic search systems, vector databases, RAG-based architectures, and LLM orchestration patterns.
• Translate business requirements into a well-formed technical design and help bring that design to life with the team, in an iterative fashion.
• Collaborate with cross-functional teams to define project goals, scope, and timelines as well as translate business requirements into scalable and robust software designs.
• 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 code reviews, ensure code quality, and enforce coding standards.
• Champion the adoption of AI-assisted development tools (e.g., Claude Code, GitHub Copilot, Codex) to accelerate development velocity and 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 and optimization.
• Champion architectural integrity alongside an iterative, gated delivery approach.
• Stay up to date with emerging technologies and industry trends and evaluate their potential impact on our software solutions.

Benefits

• Fully remote work with company provided equipment (laptop, software, etc.)
• Employment with a growing, casual, fun, philanthropic minded company
• Comprehensive, high-quality medical/prescription drug plan options, as well as dental and vision plan offerings.
• An employer contribution to your Health Savings Account (HSA) if you participate in a High Deductible Healthcare Plan.
• Medical Flexible Spending Accounts available.
• Dependent Care Flexible Spending Accounts available.
• Basic life insurance in the amount of $50,000 or 1 X’s your salary (whichever is higher).
• Short and long-term disability and Accidental Death and Dismemberment benefits at no cost to you.
• 401K Retirement Savings Plan with automatic enrollment at the first of the month following 60 days of employment at 5% to help you secure your financial freedom.
• Paid Time Off (PTO)/Holiday.