Software Engineer

POSITION SUMMARY

Wellspring is seeking a Software Engineer to build and evolve the Accolade platform with a cloud-native, AI-first mindset. This is a deeply hands-on role — you will spend most of your time writing, reviewing, and shipping production code. You will do that work AI-first: contributing to how the team writes, reviews, tests, and ships software by making agentic workflows a natural part of how we work — not an add-on. You will work alongside expert engineering, product, and design colleagues to deliver high-value, end-to-end customer experiences through collaborative processes in a flexible, remote-first environment.

DUTIES AND RESPONSIBILITIES

Hands-On Engineering & Delivery

• Design, build, and ship features across the Accolade platform — owning substantial pieces of work end to end, from technical approach through production operation.

• Write high-quality, well-tested production code, and set the standard for the rest of the team through the work you deliver rather than the documents you write.

• Raise the quality bar through thorough code review, constructive feedback, and pragmatic refactoring of the code you work in.

• Build and maintain containerized services, contributing to deployment pipelines, environment consistency, and scalable workload management.

• Apply and reinforce sound practices for security, observability, and resilience in the systems you build.

• Debug and resolve complex production issues across the stack, and feed what you learn back into the codebase.

• Evaluate and responsibly adopt emerging technologies, with particular emphasis on AI and agentic systems, by prototyping and proving them in real work.

AI-First Development Practices

• Work AI-first as a member of the team — modeling in your own day-to-day what it looks like to build software with AI as a core part of the workflow, not a productivity shortcut.

• Contribute to the team’s shared norms for how engineers engage with AI tools throughout the full development lifecycle: writing and reviewing code, designing systems, authoring tests, producing documentation, and debugging production issues.

• Design and build developer-facing agents and skills that meaningfully augment the team’s ability to deliver — automating routine tasks, accelerating onboarding, surfacing context, and reducing cognitive overhead.

• Compose agents from discrete, reusable skills with clear interfaces, testable behavior, and consistent patterns that the whole team can build on.

• Help shape how the team prompts, chains, and evaluates agents so that AI-assisted work is reproducible, reviewable, and held to the same quality bar as hand-written code.

• Share what you learn using AI in development so those insights improve our tooling, processes, and engineering culture over time.

• Keep up with the rapidly evolving landscape of agentic development paradigms and bring that knowledge back to the team through documentation, working examples, and demos.

• Help the team spot where AI-assisted workflows can have the greatest impact, and where they are the wrong tool for the job.

AI in the Product

• Build agentic capabilities into the Accolade product, implementing them safely, reliably, and to the same standards applied to the rest of the platform.

• Collaborate with product and design colleagues to assess opportunities where AI can enhance the customer experience, contributing technical judgment on feasibility and risk — and prototyping to find the answer where it isn’t obvious.

Delivery & Collaboration

• Break complex problems down into well-scoped, deliverable work, and help keep the team’s backlog grounded in technical reality.

• Participate actively in Agile ceremonies: sprint planning, design reviews, and retrospectives.

• Collaborate cross-functionally with Product, Design, QA, and DevOps to ensure end-to-end solution quality.

• Mentor mid-level and senior engineers on cloud-native patterns, system design, and AI-first development practices — primarily through pairing, code review, and worked examples.

• Contribute to the continuous improvement of our engineering culture, metrics, and software development practices.

TECHNICAL SKILLS

AI-Driven Development

• Hands-on fluency with AI-assisted development tools — using them daily and understanding their strengths, failure modes, and appropriate limits.

• Experience building and orchestrating agents: designing agent loops, managing context and memory, composing multi-step pipelines from discrete skills, and handling failure modes gracefully.

• Ability to define reusable, well-scoped skills with clear interfaces and predictable behavior — the building blocks of reliable agentic workflows.

• Prompt engineering as a first-class discipline: structured prompting, output validation, iterative refinement, and the ability to teach these practices to others.

• Practical experience evaluating agent behavior: defining what good looks like, building evals, and holding AI-generated work to the same standards as hand-authored code.

• Ability to identify which parts of a development workflow are good candidates for automation or AI assistance and which are not.

Cloud Native & Platform

• Strong working command of containerization and orchestration — building and running services that are scalable, reliable, and operationally simple.

• Experience with major cloud platforms and their managed services, with a preference for platform-native solutions over custom infrastructure.

• Infrastructure as code practices applied consistently across environments.

• Building and maintaining CI/CD pipelines with an emphasis on fast feedback, automated quality gates, and safe deployment patterns.

• Distributed systems fundamentals applied in practice: service communication, event-driven patterns, observability, and fault tolerance.

Application Development

• Expertise in C# / .NET — platform internals, async programming, and performance optimization.

• API design and implementation using ASP.NET Core, including REST principles, versioning, and middleware patterns.

• Relational database design, ORM usage, and T-SQL query optimization.

• Front-end development with React and TypeScript, including component design and state management patterns.

• Proficiency with modern JavaScript/TypeScript, HTML, and CSS.

Tooling & Quality

• Performance profiling and analysis across both server and client layers.

• Comprehensive testing strategies spanning unit, integration, and end-to-end coverage.

• Security fundamentals: secure coding practices, secrets management, and awareness of common vulnerability classes.

PERSONAL & INTERPERSONAL SKILLS

• Takes an AI-first approach to their own work — experiments constantly with new tools and practices, and shares what works with the team.

• Able to translate complex technical trade-offs into clear, actionable language for both engineers and non-technical partners.

• Leads through craft — influences through the quality of the work, clear reasoning, and example rather than authority.

• Thrives in a highly agile environment and adapts quickly to new information and shifting priorities.

• Excellent written and verbal communication skills; writes design docs, pull request descriptions, and documentation that others can act on.

• Strong sense of ownership — self-starting, proactive, and accountable for outcomes.

• Pragmatic over dogmatic — chooses the right tool for the job and knows when good enough is the right answer.