About UsAt Pinpoint Global, we build training and compliance platforms that organizations rely on to keep their teams skilled, certified, andaudit-ready.We'repart of theValsoftEdelweiss Software Group — a large-scale portfolio of vertical market B2B SaaS companies — and weoperatewith a startup mindset: high ownership, high velocity, and real ROI.Our core stack is ASP.NET MVC + MS SQL — battle-tested and ready to evolve.We'relooking for true builders: engineers who orchestrate systems, ship production-grade AI, and modernize massive legacy codebases at speed.The RoleYou'llembed directly in our engineering team, working hands-on inside our .NET codebase and broader product suite. Your mission is to act as an organizational force multiplier — turning legacy inefficiencies into intelligent systems, increasing Net Revenue Retention (NRR), and driving measurable business impact through production-grade AI.This is a full-stack role with direct product impact. If you enjoy owning problems end-to-end, have a relentless bias toward action, and thrive on shipping real systems at high velocity — this role is for you.What You'll DoBuild & Ship AI SystemsIntegrate AI capabilities (LLM APIs, intelligent automation, personalization) into our ASP.NET MVC productsDesign, develop, and deploy production-grade, secure AI systems using scalable polyglot microservicesIntegrate enterprise LLMs (Anthropic Claude, OpenAI, Google Gemini) into SaaS platforms via fault-tolerant API routing gatewaysDevelop autonomous multi-agent workflows using parallel orchestration tools (Claude Code CLI, OpenAI Codex)Build recent product surfaces — smart content recommendations, automated compliance tracking, AI-assisted reportingRapidly prototype →validatevia adversarial testing → deploy → iterateArchitect AI InfrastructureImplement complex RAG pipelines andoptimizetrade-offs between massive-context hydration and multi-stage semantic retrievalBuild vector databases (Pinecone,Weaviate, FAISS) and manage persistent document embedding queuesBuild polyglot microservices handling long-running tasks and streaming viaWebSocketsand Server-Sent EventsEnsure SOC 2 compliance,



data residency controls, and deterministic execution through policy-as-code agentic governanceDeploy and scale models within secure managed cloud boundariesModernize& CollaborateIdentifyhigh-impact modernization opportunities across our training and compliance platformHelp migrate legacy features into scalable, AI-native architectures using agentic swarm coding and automated refactoringArchitect zero-touch CI/CD pipelines with adversarial gating and AI-driven test automationIntegrate synthetic red teaming into CI/CD to prevent prompt drift, reward hacking, and logic degradationWork directly with non-technical stakeholders to translate ambiguous business problems into secure, scalable AI solutionsCollaborate with product and design to ship features end-to-endRequired Technical SkillsCore Engineering3–5+ years of enterprise software development experience with strong full-stack web fundamentalsHands-on experience with .NET / ASP.NET MVC (our core stack) and C#Fluency across popular languages and frameworks: Python, JavaScript, TypeScript, .NET,NextJSSolid understanding of relational databases — MS SQL experience a plusBackend experience designing polyglot APIs, decoupled async microservices, and persistent connection protocols (WebSockets/SSE)Familiarity with containerization (Docker, Kubernetes) and multi-region cloud infrastructure (AWS, Azure, or GCP)AI & ML SystemsPractical experience integrating AI/ML APIs or building AI-powered features in productionEnterprise LLM integration and dynamic API routing (OpenAI, Anthropic, Gemini)Multi-agent orchestration and advanced CLI tooling (Claude Code, OpenAI Codex)Mastery of AI IDE tooling: Cursor for repo-wide reasoning, GitHub CopilotRAG pipeline design: dynamic chunking, vector databases,



embedding managementCustom evaluations (LangSmith), structured outputs, and managed fine-tuning in secure cloud environmentsMLOps& Process AutomationZero-touch CI/CD pipelines and advanced Git workflows (includingworktreeisolation for autonomous sub-agents)Unit test and benchmark automation integrated with AI-driven testing frameworksAdversarial LLM testing and automated synthetic red-teamingHallucination mitigation, enterprise guardrails, and deterministic policy-as-code executionReal-time token/credit consumption tracking and dynamic access limit monitoringBonus PointsExperience with prompt engineering, RAG pipelines, or agentic workflowsFamiliarity with refactoring or re-architecting legacy .NET applicationsBackground in regulated industries: HR tech, e-learning, compliance, LMS platformsKnowledge of SOC 2 audit requirements and compliance automation toolingWho You AreHighly hands-on — you ship, not just design; youoperateat velocity by orchestrating autonomous toolsEntrepreneurial startup mindset — you spot legacy inefficiencies and act with a bias toward rapid actionComfortable with ambiguity — you scope, own, and deliver independentlyBusiness-oriented —you care about ROI, operational leverage, and financial metrics like NRR and CACStrong product instincts — you think about the user, not just the implementationFast learner — you track real-time shifts in AI ecosystems, APIs, and infrastructurePragmatic — you use the right secure enterprise tool for the bottleneck, not just the flashiest oneTech StackASP.NET MVC · C# · MS SQL · Python · TypeScript · LLM APIs (Anthropic, OpenAI, Gemini) · RAG / Vector DBs · Docker · Kubernetes · Azure / AWS / GCP · REST APIs ·WebSockets· HTML/CSS/JSWhy JoinShape the AI strategy of a growing compliance and training platformOwn meaningful features from day one — not just tickets in a backlogReal modernization challenge: legacy codebase + greenfield AI opportunity in parallelCollaborative, low-ego team that ships and iterates fastStartup velocity inside an established, well-resourced corporate portfolio#J-18808-Ljbffr

📌 Ai Engineer - C$169,000 - C$253,000 A Year (Winnipeg)
🏢 AutoCanada
📍 Winnipeg