Staff Software Engineer

Upside is a software consultancy built by engineers, for engineers. We partner with global companies to solve real, complex technical challenges. We’re deep into Applied AI and R&D, building both production-grade platforms for clients and our own open-source tools like Enthusiast (Agentic AI framework). We operate in a Forward-Deployed model. We don’t sit behind a wall of specs or wait for the tickets. We get into the trenches with the client, identify the actual challenges, and take full ownership of the solution. Our teams are small (3–9 people), autonomous, and cross-functional. What it means for you You are the technical North Star. You’ll be a peer and advisor to CTOs and founders, shaping the technical direction of their business. This is a hands-on leadership role: you’ll stay close to the code while guiding teams through massive architectural decisions. You have the mandate to choose the best tools and the responsibility to ensure technical excellence is a lived standard, not just a goal. You’ll mentor the next generation of engineers while pushing the boundaries of Applied AI. This is about scaling both systems and people. Role Overview As a Staff Software Engineer, you will guide engineering teams in delivering AI-driven solutions and production-grade platforms. You’ll balance high-level strategy with execution, ensuring that our architecture is resilient and our engineers are growing. Responsibilities Technical Vision: Drive the architecture and technology choices for large-scale, distributed systems. Strategic Partnership: Partner directly with clients and founders to co-create solutions that move the needle. Mentorship: Foster a culture of knowledge sharing and constructive feedback. Systemic Problem Solving: Anticipate technical debt and architectural risks before they impact the business. AI Leadership: Identify and implement opportunities to integrate AI/ML into client ecosystems.