Description About the Role

We're hiring a Staff Software Engineer to own architecture and design decisions for our platform, including the modernization of legacy enterprise systems into modern, cloud-capable solutions. You'll operate with significant autonomy, act as a force multiplier for the rest of the engineering team, work closely with our Head of R&D; as a technical backup, and be a candidate for broader technical responsibility across projects as you prove yourself. This is a hands-on, high-ownership role on a lean, three-person engineering team - small enough that your architectural calls ship and show results in weeks, not after months of committee review. You'll be a player-coach: as comfortable writing code as setting direction, designing and deciding as well as implementing, delegating, and growing the engineers around you. In an AI-assisted development era, we value sound judgment and design thinking as much as implementation speed - you'll have real latitude to use tools like Claude and Cursor to move faster, not just permission to.

Responsibilities Architecture & Technical Ownership

Own architecture and design decisions for the systems you're responsible for, favoring pragmatic, right-sized solutions over unnecessary complexity, and weighing trade-offs (build vs. buy, hosted vs. on-premises, integration approach) with senior-level judgment.

Lead the modernization of legacy systems into maintainable, cloud-capable architectures without disrupting the business relying on them.

Review requirements and designs early to flag architectural risk, technical debt, and feasibility gaps before they become expensive.

Own solution-level architecture documentation - decisions, trade-offs,



and the reasoning behind them - so the system stays understandable at a glance, not just in your head.

Hands-On Delivery

Design and implement significant parts of the system yourself - this role ships production code, not just plans.

Own what you build end-to-end, including its health after it ships - if it breaks in production, you're part of fixing it.

Apply AI-assisted development tools (e.g., Claude, Cursor) to work faster across design, implementation, and documentation, with informed judgment about where they genuinely help.

Team Leadership & Mentorship

Delegate work effectively and help pull the wider team forward, rather than carrying everything yourself.

Mentor other engineers through code review, design discussion, and day-to-day guidance, as an individual contributor rather than a people manager.

Act as a technical backup to the Head of R&D;, and take on broader technical responsibility across projects over time.

Product & Customer Judgment

Translate ambiguous customer needs - including regulated-industry and enterprise requirements - into sound technical designs.

Work closely with product owners, QA, and subject-matter experts to understand how the product is used and where the real risk lies.

Communicate trade-offs, risks, and plans clearly to both technical and non-technical stakeholders.

Ways of Working





Operate independently in ambiguous, shifting-priority conditions, setting your own priorities rather than waiting to be told what's next.

This role has no fixed lane - architecture, hands-on coding, mentoring, production support, whatever's needed. You pick it up rather than waiting for it to be assigned.

Participate in and help shape Agile ceremonies (stand-ups, sprint planning, retrospectives).

Our Stack

Frontend: React (TypeScript) single-page applications.

Backend: polyglot services, primarily .NET and Python, built as event-driven microservices.

Databases: PostgreSQL, SQL Server, and Oracle.

Infrastructure: containerized, Kubernetes-based deployments with owned CI/CD pipelines.

Deployment model: hybrid - both cloud-hosted (SaaS) and on-premises enterprise environments.

API & identity: API gateway / service mesh patterns and OIDC-based identity providers.

We're also maintaining and modernizing some longer-standing legacy systems - comfort reading and evolving older architectures is part of the job.

Requirements What You'll Bring Must-Have

8+ years of professional software engineering experience, including real ownership of architecture and design decisions - not just executing someone else's plan.

Proven track record modernizing legacy systems into maintainable, cloud-capable architectures.

Full software development lifecycle experience: requirements through design, implementation, testing, release, and operations.

Robust relational database fundamentals (e.g., PostgreSQL, SQL Server, or Oracle).

Experience in regulated-industry and/or enterprise software environments, with a real apprec

📌 Staff Software Engineer (Winnipeg)
🏢 S&W Technologies
📍 Winnipeg