Principal Software Engineer

Wonder Group • Chicago, IL

3d • $244,000 - $253,500

About The Position

Wonder is seeking a Principal Engineer to establish the technical direction for a new team and bring AI-enabled development practices to Wonder Engineering. The role defines architecture and guides delivery of solutions for context fragmentation, MCPs and CLIs, skills, sub-agents, and integrations connecting AI tools with Wonder’s codebases and systems. It also shapes AI-assisted workflows for code generation, review, testing, documentation, refactoring, and on-call and incident management.

The Principal Engineer will introduce proven AI-tooling patterns from outside Wonder and partner with engineers across the company, senior engineering leadership, and platform, infrastructure, and application teams. The role establishes standards and architecture for AI-native developer tooling, autonomous development agents, cloud agent solutions, access controls, and guardrails. It also sets strategy for AI-assisted review and triage, model routing and cost optimization, and measuring developer velocity and the outcomes produced by AI spending.

The position guides cross-team technical outcomes, weighs build-versus-buy, cost, and risk tradeoffs, and helps land solutions in production. It also requires producing clear strategy documents, specifications, and documentation; communicating technical tradeoffs across departments and leadership levels; and mentoring senior engineers in durable, auditable AI-assisted engineering practices.

Requirements

• Bachelor’s or Master’s degree in Computer Science or a related field, or equivalent practical experience.
• 10+ years of professional software engineering experience, including recent hands-on work building with or on top of LLM-based tooling such as agents, MCP servers, or coding assistants.
• Direct experience integrating AI tools into real development workflows, such as code review, testing, code generation, or documentation, beyond individual use as an end user; ideally at organizational scale.
• Strong system design skills and a track record of owning tools or platforms end-to-end, from design through adoption across multiple teams.
• Comfort operating with ambiguity and shaping practices for a new team without established playbooks.
• Experience designing and consuming APIs, webhooks, or other integration or message-based systems.
• Experience building developer tooling, internal platforms, CI/CD systems, or other software primarily used by engineers.
• Pragmatic problem-solving skills and ability to troubleshoot complex technical obstacles.
• Excellent communication and interpersonal skills, including ability to drive technical discussions with engineers and leaders across multiple teams up to senior director level.

Nice To Haves

• Experience with Java/JVM and/or Python.

Responsibilities

• Set the architecture for context aggregation, MCPs and CLIs, skills, and sub-agents that provide AI coding tools with sanctioned, reliable access to Wonder’s codebases, services, and systems.
• Set direction for autonomous development agents and cloud agent solutions, including access controls and guardrails.
• Identify effective AI-assisted development practices for review, testing, code generation, and documentation, and translate them into standards suited to Wonder’s technology stack, scale, and constraints.
• Set strategy for pre-review and triage tooling that automates mechanical and policy issues before human review, and define standards for reviewing AI-generated code.
• Define strategy and architecture for AI cost optimization and model selection and routing.
• Define and measure developer velocity and connect AI spending to outcomes.
• Guide technical direction for developer tooling, coordinate deliverables across teams, weigh build-versus-buy, cost, and risk tradeoffs, and partner with relevant teams and engineering leadership to deliver solutions to production.
• Write strategy documents, specifications, and documentation; provide, seek, and incorporate feedback; and communicate technical tradeoffs to audiences across departments and leadership levels.
• Mentor senior engineers in building durable, auditable AI-assisted engineering practices.

Benefits

• Competitive compensation package with equity.
• 401(k).
• Choice of medical, dental, and vision plans.
• Company-paid short- and long-term disability coverage.
• Paid time off, including flexible time off for exempt employees, paid vacation for non-exempt employees, and paid sick leave in compliance with applicable law.
• Paid parental leave.
• Discounted meals and exclusive perks across the Wonder family of brands.

What This Job Offers

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