Software Engineer

Wellspring Worldwide

3d•Remote

About The Position

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.

Requirements

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.
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.
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.
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.
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.

Responsibilities

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.
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.
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.
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.