Staff Software Engineer

This is a fully remote position, open to applicants in Wisconsin.

📋 Description

• Take charge of the architecture for the team's domain, encompassing services, data flows, integration points, and potential failure modes.

• Create products and services designed for iterative autonomous development and scalability for the future.

• Spearhead modernization initiatives involving PHP monoliths and transitioning Java services to TypeScript.

• Develop an understanding of related systems, including grading, marketplace, CRM, payments, identity, and data/ETL.

• Set standards for security, testing, observability, and operational excellence.

• Drive the adoption of AI-assisted engineering standards and guidelines throughout the technology organization.

• Identify opportunities for AI agents in legacy code comprehension, test generation, and migration scaffolding.

• Oversee moderate-scope projects lasting one to two quarters.

• Coordinate engineers, stakeholders, and dependencies to ensure predictable delivery.

• Plan development efforts using a value-versus-cost prioritization approach.

• Identify and communicate any blockers and delays encountered.

• Encourage knowledge sharing and maintain thorough documentation.

• Cultivate relationships with teammates, managers, business stakeholders, and senior engineers.

• Mentor senior and mid-level engineers through design reviews, pairing sessions, and constructive feedback.

• Enhance the organization's AI fluency by sharing workflows, prompts, and agent configurations.

⛳️ Requirements

• Over 8 years of professional experience in software engineering.

• Proven technical leadership in projects involving multiple engineers over several quarters.

• Expert-level backend engineering skills in TypeScript/Node.js and/or Java.

• Proficient in working with TypeScript, Java 21, PHP, Python, and C#.

• Practical experience with React/Next.js frontends, API and service layers, relational data stores, and infrastructure.

• Background in modernizing legacy systems via strangler-fig migrations, service extraction, or platform re-architecture while under live traffic.

• Extensive expertise in PostgreSQL and MySQL, including data modeling, migrations, and performance optimization.

• Strong foundation in distributed systems concepts, such as REST, GraphQL, gRPC, SQS, idempotency, and failure handling.

• Production experience with AWS, specifically in ECS, Lambda, networking, and IAM.

• Proficient in infrastructure-as-code, particularly with AWS CDK and/or Terraform.

• Experience enhancing engineering standards through testing, observability, documentation, and incident response practices.

• Daily hands-on experience with AI coding assistants and agentic tools like Claude Code, Copilot, or Cursor.

• Familiarity with integrating AI tools into CI, code review, and documentation workflows.

• Sound judgment regarding the verification, security, and limitations of AI-generated code.

• Exceptional written and verbal communication skills for both technical and business audiences.

• Valid U.S. work authorization verified through e-Verify.

🏝️ Benefits

• Flexible remote work arrangement.

• Possible on-site interview during the final stages for remote positions.

• Commitment to equal employment opportunities.

• Accommodations available for interviews and applications.

• Employer-sponsored e-Verify work authorization validation.