Systems Architect (AI & Cloud) - Remote

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<p><strong>What We’re About</strong></p> <p>At <strong>CentralSquare</strong>, we don’t just build software - we power public servants and uplift communities with <strong>Hero-Grade</strong> Technology. Every line of code, every feature we deliver helps heroes across North America protect, serve, and save lives. When you join us, you become part of a mission-driven team creating technology that makes communities safer and stronger.</p> <p><strong>Your Growth Matters.</strong> We believe heroes deserve opportunities to rise. That’s why we invest in your career with mentorship, learning programs, and clear paths for advancement. If you’re motivated, there’s no limit to how far you can go.</p> <p><strong>Your Commitment Deserves Reward.</strong> We offer competitive compensation and a benefits package designed to support your life inside and outside of work—tuition reimbursement, parental leave, paid volunteer hours, and unlimited PTO. Plus, our flexible work environment gives you the freedom to balance your heroic work with personal well-being, whether you’re in the office or remote.</p> <p>Join us and help build the tools that power real-life heroes. Together, we make a difference.</p> <p><strong>The Opportunity</strong></p> <p>We are looking for a Senior Architect who will define and drive how AI builds software across our platform — not just writing code with AI assistance, but designing the orchestration layers, agent pipelines, and spec-driven workflows that allow AI to produce production-quality output at scale. This is an architecture role where your technical depth in C#/.NET and cloud-native systems meets a hands-on obsession with AI-first engineering practices.</p> <p>You will serve as a technical leader and architect across multiple product teams, driving cloud-native modernization of multiple products. We need architects who can own the technical vision for that system and elevate every team’s ability to execute against it.</p> <p><strong>What You’ll Do</strong></p> <ul> <li>Define and own the cloud-native architecture for C# services, APIs, and containerized workloads running on AWS EKS, including service decomposition, data access patterns, and cross-cutting concerns.</li> <li>Lead monolith decomposition strategy — identifying bounded contexts, defining service boundaries, and creating incremental extraction plans that let teams carve out services from legacy systems without big-bang rewrites.</li> <li>Architect the migration from legacy ASP.NET WebForms (.aspx) or other legacy UI systems to modern SPA frameworks (Angular or equivalent), defining the incremental migration path, component architecture, state management patterns, and coexistence strategy that lets teams move page by page without a full rewrite.</li> <li>Drive OIDC modernization across products — migrating from legacy or inconsistent authentication patterns to standards-based OIDC flows</li> <li>Architect event-driven and event-sourced systems, designing domain event contracts, message schemas, and replay/projection patterns that support offline capability, audit trails, and eventual consistency across distributed services.</li> <li>Design and implement GraphQL APIs as a unified query layer across decomposed services, including schema federation, resolver architecture, and performance considerations like query complexity limits and dataloader patterns.</li> <li>Design and evolve AI orchestration pipelines — multi-agent architectures, sub-agent delegation, spec-to-code-to-test workflows — that serve as the primary mechanism for code production across teams.</li> <li>Prepare products for AI integration by designing MCP-ready architectures — exposing product capabilities as well-defined tool interfaces, structured context providers, and machine-consumable APIs that allow AI agents and third-party integrations to interact with our platform programmatically.</li> <li>Establish the specification framework that feeds AI-driven development: what a spec must contain, how it maps to architecture context, data contracts, and behavioral validation, so that AI output is predictable and production-grade.</li> <li>Drive legacy system refactoring strategy, making pragmatic decisions about what to rewrite, what to wrap, and what to strangle — balancing technical debt reduction against delivery velocity and risk.</li> <li>Architect for resilience and scalability — circuit breakers, retry policies, graceful degradation, horizontal scaling patterns, backpressure handling, and health check architectures that keep systems stable under load and failure.</li> <li>Define and enforce observability architecture — distributed tracing, structured logging, metrics, and DAU telemetry — as a first-class system concern, not an afterthought.</li> <li>Integrate AI tooling (Claude, Copilot, custom agents) into development workflows, continuously raising the ceiling on what automated pipelines can reliably deliver.</li> </ul>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...