Director of Software Engineering

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

The Director of Engineering will lead the engineering team responsible for the company's next-generation SaaS platform. This is a remote position (must be based in the Midwest or on the East Coast) reporting directly to the CTO. This individual will manage a team of five engineers today, with plans to approximately double the team over the next 6-12 months.

This is a hands-on, player-coach leadership role with ownership over how the platform is built and delivered. You will provide technical and architectural direction while developing the team, establishing engineering standards, and building the processes needed to support continued growth.

Why Consider This Opportunity?:

• Path to VP of Engineering: Join a fast-growing organization in a position intentionally designed to expand toward VP of Engineering-level responsibilities as the company and engineering team scale.
• Build & Scale the Team: Lead a team of five engineers today with the support and investment to approximately double the organization over the next 6-12 months. You will serve as the hiring manager for every engineer added to the team.
• Own the Engineering Function: Take ownership of the team's SDLC, development standards, performance benchmarks, documentation, and overall engineering processes.
• Lead a Next-Generation Platform: Take engineering leadership of a new SaaS platform that has begun onboarding customers with additional implementations planned over the coming months.
• High Visibility & Executive Exposure: Work closely with the CTO, CISO, Product, and other leaders while playing a highly visible role in the continued development of the platform.

Key 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.

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.