At Vanta, our mission is to help businesses earn and prove trust.We believe that security should be monitored and verified continuously, and we empower companies to practice better security and prove it with ease. Vanta has a kind and talented team, and while some have prior security experience, many have been successful at Vanta without it. Build the systems, infrastructure, and developer workflows that make AI-powered engineering more useful, reliable, and easy for Vanta engineers to adopt.

The AI DX team is building the foundations for a more autonomous software development experience at Vanta, including background agents, agent evaluation systems, and tooling that helps engineers work more effectively with AI. The team combines software engineering, developer experience, AI systems, and product thinking to turn emerging capabilities into reliable workflows used in real engineering work. As a Senior Software Engineer on the AI DX team, you'll help shape these systems from the ground up.

You'll work directly with engineers to understand friction in their workflows, build practical solutions, and use evidence from real usage to continuously improve quality, reliability, and adoption.

What you'll do as a Senior Software Engineer at Vanta: Develop systems for evaluating agent performance using task outcomes, quality measures, human intervention, cost, and other signals. Create evaluation sets and feedback loops that help AI systems improve over time through regular review, tuning, and correction. Improve how engineers discover, understand, and use shared AI tools and workflows.

Evaluate AI development tools, including code generation, AI-assisted review, and testing, against real engineering needs,



and help integrate the ones that prove useful. Create clear guidance and documentation that helps engineers adopt new AI-enabled development practices. Influence the foundations of an autonomous software factory, including systems that help agents complete bounded engineering tasks safely and effectively.

Help the team move ambiguous, dependency-heavy projects from early exploration through reliable delivery. Raise the quality bar through thoughtful code reviews, technical design discussions, testing, observability, and attention to reliability and security. Substantial industry software engineering experience.

Experience taking technical leadership roles on teams or complex projects.

Experience improving AI systems, creating evaluation sets, and driving quality hill-climbing through measurement and iteration. Strong software engineering fundamentals and experience designing, building, testing, and operating reliable systems.

Experience with developer tooling, AI-enabled workflows, agentic systems, infrastructure, or related technical domains. A track record of working through ambiguity, decomposing complex problems, managing dependencies, and helping projects reach completion.

Product judgement and curiosity:



you bring solid technical opinions while staying focused on building platforms that meet users where they are. Strong written and verbal communication, with the ability to explain technical concepts clearly and create guidance that helps others adopt new tools. Uses AI in day-to-day work to amplify their skills and strengthen their outcomes, applying it across routine workflows, actively building fluency through experimentation, and exercising sound judgment to ensure AI‑assisted work meets a high quality bar.

Industry-competitive salary and equity 100% covered medical, dental, and vision benefits with dependents coverage Pension contribution 16 weeks paid Parental Leave for all new parents Remote workspace, internet, and cellphone stipend Flexible work hours and location 21 days of Vacation Time and 80 hours of Sick Leave 11 company-paid holidaysVirtual team building activities, lunch and learns, and other company-wide events! LI-remote We do not discriminate on the basis of race, gender identity, age, religion, sexual orientation, veteran or disability status, or any other protected class.

About

VantaWe started in 2018, in the wake of several high-profile data breaches. Online security was only becoming more key, but we knew firsthand how hard it could be for fast-growing companies to invest the time and manpower it takes to build a solid security foundation.From our early days automating security monitoring for compliance standards like SOC 2, HIPAA and ISO 27001 to creating the world's leading Trust Management Platform, our vision remains unchanged. Now more than ever, making security continuous - not just a point-in-time check - is essential.

📌 Senior Software Engineer, Ai Developer Experience (Winnipeg)
🏢 Vanta
📍 Winnipeg