Principal Software Engineer

Skillable

4d • $150,000 - $200,000 • Remote

About The Position

Skillable is hiring a Principal Software Engineer to set the technical bar for a team and lead complex software feature design and delivery, including through AI-assisted development workflows. The role serves as the primary architect, reviewer, and decision-maker for work delegated to AI agents, and builds the context, reusable skills, agent workflows, prompt frameworks, and automated checks that enable high-quality, maintainable, scalable software. It owns delivered software quality, comprehensive automated testing and verification, and the management of risks related to AI-generated solutions.

The engineer brings clarity to undefined problems, communicates technical matters to technical and non-technical audiences, and leads collaboration in a cross-functional scrum team. The role is accountable for delivery, pace, quality, scoping, staging, estimates, documentation, mentoring, and engineering standards. It also advances integration solutions by proposing and evaluating technologies and processes, recommends practices for non-functional requirements, contributes to hiring, and participates in an on-call rotation during evenings, weekends, or holidays. The position is fully remote in a home-office setting, with periodic travel of up to approximately 10%. Skillable can hire only candidates whose primary residence is in the states listed in the posting.

Requirements

• Bachelor’s degree in a related field or equivalent work experience.
• 15+ years of professional software development experience in an agile product team.
• 10+ years working with .NET Framework and C#, and experience with TypeScript or JavaScript.
• At least 1 year of professional experience in a lead position or unofficially leading cross-functional projects.
• Experience mentoring and developing team members and promoting best practices and standards.
• Hands-on experience delegating real implementation work to AI agents and reviewing and verifying the resulting engineering work, rather than using autocomplete alone.
• Regular professional use of modern AI tools or agent tools, such as GitHub Copilot and Claude Code or similar, as a standard practice in building production software.
• Strong fundamentals in system design, debugging, and code review.
• Demonstrated experience with MSSQL and Entity Framework.
• Proficiency collaborating with UX designers to translate designs into working software.
• Proficiency creating and consuming RESTful APIs.
• Proficiency in unit testing, including writing comprehensive, maintainable, and efficient tests for correctness, reliability, and performance.
• Experience working with cloud-native applications.
• Ability to proactively address challenges and seek continuous improvement.
• Self-motivation and ability to contribute effectively with minimal supervision.
• Ability to adapt to changing project needs while maintaining quality and focus.
• Ability to participate in team on-call rotation during evenings, weekends, or holidays for emergency support or special events.

Nice To Haves

• Experience with hands-on technical training environments, virtual labs, or learning platforms.
• Evidence of building AI-tool scaffolding, such as custom agents, MCP servers, evaluation harnesses, or team/department enablement.
• Experience with authentication technologies such as OIDC, OAuth, or SAML.
• Experience with NextJS or ExpressJS.
• Experience building pipelines and applying DevOps practices.

Responsibilities

• Set the technical bar for the team and lead the design and scope of complex software features, turning them into well-defined implementation plans.
• Guide AI agents through feature development by framing problems, setting constraints, reviewing output, and making technical decisions aligned with business requirements and standards.
• Build scaffolding for AI-assisted development, including project context management, reusable skills, agent workflows, prompt frameworks, and automated quality checks.
• Drive automated testing and verification for features before release, tying unit tests and validation scenarios to requirements.
• Own delivered software quality by reviewing AI-generated work, challenging assumptions, identifying gaps, and validating that solutions address the problem.
• Identify and mitigate risks in AI-assisted development, including security, maintainability, correctness, and long-term sustainability risks.
• Improve AI-driven engineering workflows, tooling, agents, and practices used by other engineers.
• Frame undefined problems, set constraints, and provide workable starting points where no established pattern exists.
• Explain complex topics clearly, facilitate healthy disagreement, and consult others for technical input before group decisions.
• Create and maintain documentation of features, design decisions, configurations, and other key technical areas.
• Lead collaboration with developers, QA engineers, designers, and product experts in a cross-functional scrum team.
• Manage team delivery, pace, and quality by scoping and staging work across team members and representing the team in cross-functional meetings.
• Define feature scope and estimates to support accurate cost and timeline projections.
• Propose, prototype, and champion technologies and processes that advance Skillable integration solutions.
• Mentor team members, develop talent, resolve technical friction, communicate direction, and establish team alignment and quality practices.
• Propose alternate designs that improve time-to-market or reduce cost or complexity.
• Explore and recommend technologies, patterns, and methods for the technical and product roadmap.
• Recommend standards and best practices for non-functional requirements, including performance, usability, reliability, adaptability, security, legal, and operational considerations.
• Participate in the team on-call rotation during evenings, weekends, or holidays for emergency support or special events.
• Review work consistently to maintain quality and avoid errors.
• Contribute to interviewing and selecting new team members.
• Support and promote company values through positive interactions with internal and external stakeholders.
• Participate in other strategic business initiatives or special cross-functional projects as required.

Benefits

• Fully remote work with a monthly stipend for office services and supplies.
• Medical insurance with two plan options, dental insurance with two plan options, and vision insurance.
• Health savings account with employer contributions, healthcare spending accounts, dependent care spending accounts, and an employee assistance program.
• Group paid life insurance, group paid short- and long-term disability insurance, and voluntary life/AD&D insurance.
• Accident and critical illness coverage options.
• 401(k) with company match.
• Tuition reimbursement.
• Healthy lifestyle reimbursements, including up to $750 annually for qualifying wellness choices such as gym memberships, fitness classes, or healthy meal plans.
• Unlimited PTO, paid holidays, bereavement leave, parental leave, caregiver leave, and paid FMLA leave.
• Opportunity to log off at 2:00 p.m. local time every Friday when caught up on work and deliverables.
• Full company closure during the 4th of July holiday week.
• Monthly $200 stipend for office expenses.
• Access to pet insurance.
• Access for employees and dependents to Skillable learning opportunities through its product.

What This Job Offers

• Job Type: Full-time
• Career Level: Principal