Remote Software Engineering Teaching Jobs in Chicago, IL

Gigantic Playground is hiring a Lead Full-Stack Software Engineer & Architect to own technical direction across multiple client engagements. This role requires prior software agency experience and comfort operating in a fast-moving, multi-client environment. You will define architecture, lead engineers, and partner directly with clients to deliver complex, production-grade systems.

This is a fully remote role with occasional travel for client engagements, on-site installations, or internal planning. Candidates based in San Diego may work from our headquarters but are not required to do so.

The Gigantic Playground team specializes in envisioning and implementing innovative ways for end-users to interact with technology, often in ways that may not resemble traditional technology. The team oversees the entire process, from ideation and architecture to the development and installation of Gigantic Playground experiences, in partnership with our clients.

Architecture & Technical Leadership

• Own system architecture across multiple concurrent client projects.

• Define and enforce architectural standards, design patterns, and non-functional requirements.

• Make final technical decisions on stack selection, integrations, and trade-offs.

• Design scalable, resilient systems spanning frontend, backend, cloud, and hardware-adjacent integrations.

Delivery & Execution

• Lead technical planning and execution for large, high-stakes client engagements.

• Remain hands-on in critical code paths while delegating effectively.

• Drive engineering rigor: code reviews, CI/CD, automated testing, observability.

• Own technical outcomes, including production stability and incident response.

Agency & Client Leadership

• Operate comfortably in a software agency model: shifting priorities, parallel clients, fixed timelines.

• Translate ambiguous client requirements into concrete technical plans.

• Act as senior technical authority in client meetings.

• Balance delivery speed with long-term maintainability under real-world constraints.

Team Leadership & Mentorship

• Lead and mentor senior and mid-level engineers.

• Raise the bar on system design, code quality, and technical communication.

• Guide engineers through architectural reasoning and trade-off analysis.

• Support hiring, onboarding, and technical evaluation.

Cross-Functional Collaboration

• Partner with product, design, and executive leadership.

• Communicate complex technical concepts clearly to non-technical stakeholders.

• Align technical execution with business goals and experiential outcomes.

• 10+ years professional software engineering experience.

• Demonstrated leadership as a Lead Engineer, Tech Lead, or Architect.

• Mandatory: prior experience working at a software agency or consultancy delivering client projects.

• Proven ownership of end-to-end system architecture.

• Strong client-facing communication skills.

• Deep experience delivering production systems under deadlines.

• Cares deeply about quality without over-engineering.

• Comfortable operating in ambiguity and evolving problem spaces.

• Equally excited by clean architecture and unconventional interactive systems.

• Values collaboration, humility, and clear communication.

• Naturally curious and eager to get hands-on—exploring unfamiliar software stacks, hardware platforms, and tools in service of building novel, real-world experiences.

• Modern frontend frameworks (React preferred).

• Backend systems (Node.js, TypeScript, or comparable).

• API design (REST, real-time systems).

• Cloud infrastructure (AWS strongly preferred).

• CI/CD, automated testing, monitoring, logging.

• Performance, security, and fault-tolerant system design.

• Fully remote position.

• Occasional travel required (client sites, installations, planning).

• San Diego–based candidates may work from our headquarters optionally.

• Clear, durable architectures supporting evolving client needs.

• High-quality delivery across multiple concurrent engagements.

• Engineers growing in autonomy, judgment, and technical depth.

• Confident in technical direction and execution.

• Experience with interactive installations, IoT, or real-world systems.

• Background in experience design, spatial computing, or hardware-adjacent software.

Additional Information

• This position is full time with benefits such as Medical, Dental, Vision

• 401K with a company match

• 17 Paid Holidays

• Flexible PTO