Remote SaaS Engineering Lead - Path to VP

Upside Search; Chicago (IL); Remote; USD 150,000 - 230,000; Full time

Job summary

Upside Search seeks a Director of Engineering to lead a five-engineer team and own the SDLC for a next-generation SaaS platform. This remote role (Midwest or East Coast base preferred) reports to the CTO and combines hands-on leadership with architectural direction.

You will mentor engineers, establish coding standards, and partner with Product, DevOps, and Data teams to ensure scalable, secure deployments and customer success as the platform grows.

Qualifications

• 7+ years of progressive software engineering experience, preferably within a multi-tenant SaaS environment.
• 3+ years of direct experience managing software engineers; 5+ years preferred.
• 5+ years of hands-on experience developing production applications using Python.
• Recent hands-on experience developing or supporting cloud-based applications within AWS.
• Strong understanding of SaaS architecture, cloud-native development, application scalability, and modern software engineering practices.
• Experience establishing or improving SDLC processes, coding standards, testing practices, and engineering documentation.
• Working knowledge of AI-assisted software development tools and best practices.

Responsibilities

• Lead, mentor, and develop a growing team of software engineers while establishing clear expectations around performance, collaboration, quality, and delivery.
• Provide hands-on technical and architectural leadership while remaining engaged with the codebase and development process.
• Establish, document, and continuously improve the team's SDLC, coding standards, testing practices, code review processes, and development workflows.
• Partner closely with Product to evaluate requirements, prioritize development efforts, and translate customer needs into scalable technical solutions.
• Support successful customer implementations while balancing short-term delivery needs with the long-term scalability and stability of the platform.
• Maintain a scalable, secure, cloud-native architecture and provide guidance around technical design and implementation decisions.
• Establish engineering benchmarks and provide leadership with clear visibility into priorities, delivery timelines, progress, and potential risks.
• Partner with DevOps and Data Engineering to ensure reliable deployments, platform security, and effective customer data integration.
• Help build the engineering structure, processes, and culture necessary to support continued company growth.

Skills

Leadership

Mentoring

Python development

Cloud-based applications

Tools

AWS

Job description

Upside Search seeks a Director of Engineering to lead a five-engineer team and own the SDLC for a next-generation SaaS platform. This remote role (Midwest or East Coast base preferred) reports to the CTO and combines hands-on leadership with architectural direction.

You will mentor engineers, establish coding standards, and partner with Product, DevOps, and Data teams to ensure scalable, secure deployments and customer success as the platform grows.