Staff Software Engineer

Upside

27d•Hybrid

About The Position

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.

Requirements

7+ years of building web applications, with 2+ years in a leadership role (Tech Lead or similar).
Deep mastery of Python. Ruby knowledge is a plus - it's present in some of our projects, but we are Python-first.
Proven ability to oversee complex, asynchronous, and distributed systems.
Exceptional ability to balance technical depth with business context.
You treat AI tooling (Claude, Cursor, and others) as a core part of your workflow, not a novelty - and you know how to multiply team velocity with it.
Fluent (C1/C2) English for high-level strategic discussions.
Experience with Python, Ruby, PostgreSQL, AWS, Docker, Kubernetes, CI/CD.

Responsibilities

Drive the architecture and technology choices for large-scale, distributed systems.
Partner directly with clients and founders to co-create solutions that move the needle.
Foster a culture of knowledge sharing and constructive feedback.
Anticipate technical debt and architectural risks before they impact the business.
Identify and implement opportunities to integrate AI/ML into client ecosystems.

Benefits

Built for the long run: We hire for the company, not just a project - looking for passion driven engineers who want to grow with Upside over time
Small teams, real accountability. 3-9 people per engagement. We're small by design. That means your decisions carry weight and you are visible.
Mission-critical work: We handle complex projects that move the needle for international brands. Our clients are scaling companies, established international brands, and large institutions. The systems you build will be under real load, with real stakes.
Real Ownership: You take part in the decision making process on technology and implementation..You’re empowered to take initiative, experiment, and drive solutions that create real impact.
No Micromanagement: We trust you to own your work and deliver outcomes - no unnecessary oversight.
Collaborative R&D: Contribute to targeted Open-source projects and internal AI research.
Growth through challenges: Complex problems and direct client exposure means you’ll grow by action.
Applied AI as a first-class discipline. We don't bolt AI onto projects as an afterthought. You'll identify where it genuinely moves the needle and lead the implementation - on client work and on our own open-source tooling.
The tools you want. If something makes you faster or sharper, we want you using it.
Transparent progression path. We have defined engineering levels with clear criteria - you'll know exactly what each role looks like, and what it takes to get from one to the other. No ambiguity, no waiting for someone above you to move on.