Senior Forward Deployed Engineer, AI & Automation

About Bask Health Bask Health is a software platform that enables entrepreneurs, doctors, and healthcare businesses to launch, manage, and grow direct-to-consumer telehealth businesses. Our platform brings together patient experiences, clinical workflows, pharmacy operations, and commerce tools in one place. We're an entrepreneurial, product-focused engineering team that values ownership, technical excellence, and building software that solves real problems. Engineers work closely with product teams and company leadership, take features from idea to production, and have a direct role in shaping the platform. Engineering at Bask is AI-first and builder-led. We use tools like Cursor and Claude Code throughout development while maintaining high standards for reliability, testing, and software quality. About the Role We're looking for a Senior Forward Deployed Engineer, AI & Automation to design, build, and deploy AI-powered solutions and automated workflows across Bask Health's platform. This role sits at the intersection of software engineering, artificial intelligence, and real-world business operations. You'll work closely with engineering, product, and operational teams to identify opportunities where AI and automation can simplify complex processes, improve efficiency, and create better experiences for merchants and internal users. You'll be responsible for taking AI and automation initiatives from initial discovery through production. That includes understanding existing workflows, evaluating technical approaches, building integrations, developing backend services, and ensuring solutions are reliable, secure, and maintainable. Unlike a traditional AI research role, this position is focused on applying existing AI technologies to practical engineering problems. You'll integrate large language models, build automated workflows, connect external systems, and develop production-ready software that delivers measurable operational value. You'll also help establish reusable engineering patterns for AI-powered features, including monitoring, testing, evaluation, error handling, and appropriate human oversight. We're looking for someone who enjoys working directly with stakeholders, understands how to turn ambiguous business problems into working software, and can balance rapid experimentation with strong production engineering standards. What You'll Do

• Design, develop, and deploy AI-powered applications and workflow automation solutions across Bask Health.
• Work directly with product, engineering, and operational stakeholders to understand business processes and identify automation opportunities.
• Translate complex operational requirements into scalable technical solutions.
• Build production-ready integrations with large language models and external AI services.
• Develop backend services, APIs, and automation tools using TypeScript, Node.js, or comparable technologies.
• Integrate AI capabilities into existing platform features and internal operational systems.
• Build automated workflows that connect multiple applications, APIs, and data sources.
• Develop AI-assisted tools that help teams complete repetitive or complex tasks more efficiently.
• Implement structured outputs, tool calling, and function execution within AI-powered applications.
• Design workflows that combine deterministic business logic with AI-driven capabilities.
• Build reliable integrations with third-party services using REST APIs, webhooks, and event-driven architectures.
• Develop systems for processing, transforming, and routing information between connected services.
• Evaluate opportunities to automate merchant onboarding, operational processes, and administrative workflows.
• Build reusable components and engineering patterns for future AI and automation initiatives.
• Implement validation, safeguards, and human-review steps for sensitive or high-impact workflows.
• Develop evaluation and testing strategies for AI-powered functionality.
• Monitor AI application performance, reliability, latency, and operational costs.
• Investigate and resolve issues involving AI outputs, integrations, and automated processes.
• Implement logging, error handling, retry mechanisms, and monitoring for production workflows.
• Collaborate with engineering teams to integrate AI solutions into existing applications and services.
• Work with SQL databases and application data to support automation and AI-powered features.
• Evaluate third-party AI services, automation platforms, and developer tools for practical use cases.
• Document technical architecture, implementation decisions, and operational requirements.
• Identify opportunities to convert custom automation solutions into reusable platform capabilities.
• Participate in code reviews and contribute to engineering best practices.
• Mentor other engineers on reliable AI integration and automation development.
• Take ownership of technical projects from initial discovery through deployment, maintenance, and continuous improvement.

Requirements

• 5+ years of professional experience in software engineering, forward deployed engineering, solutions engineering, or a comparable hands-on technical role.
• Strong programming experience with JavaScript or TypeScript.
• Experience developing backend applications, APIs, and services using Node.js or comparable technologies.
• Hands-on experience integrating large language models or AI services into software applications.
• Experience building automated workflows, system integrations, or operational tooling.
• Strong understanding of REST APIs, webhooks, and third-party integration patterns.
• Experience developing and maintaining production software.
• Ability to translate business requirements into technical specifications and working solutions.
• Experience integrating multiple systems, services, or data sources.
• Familiarity with prompt design, structured outputs, and practical LLM application development.
• Understanding of error handling, validation, and reliability considerations for AI-powered workflows.
• Experience working with SQL databases and relational data.
• Strong debugging and troubleshooting skills across application and integration layers.
• Experience designing maintainable, scalable backend services.
• Familiarity with cloud infrastructure and modern application deployment practices.
• Understanding of application security, authentication, authorization, and secure data handling.
• Ability to evaluate technical approaches and make sound architectural decisions.
• Experience writing tests and maintaining software quality.
• Ability to investigate and resolve complex production issues.
• Experience collaborating with product managers, engineers, and nontechnical stakeholders.
• Strong written and verbal communication skills.
• Ability to manage technical projects independently from discovery through deployment.
• Strong problem-solving skills and comfort working with ambiguous requirements.
• Ability to balance rapid implementation with long-term maintainability.
• Comfort working in a fast-moving, remote engineering environment.

Nice to Have

• Previous experience as a Forward Deployed Engineer, AI Solutions Engineer, or Automation Engineer.
• Experience building AI agents or multi-step LLM workflows.
• Familiarity with OpenAI, Anthropic, or comparable AI model APIs.
• Experience with function calling, tool use, and structured LLM responses.
• Familiarity with retrieval-augmented generation (RAG) and vector databases.
• Experience with AI orchestration frameworks such as LangChain or LangGraph.
• Experience developing AI evaluation frameworks or automated quality checks.
• Familiarity with prompt versioning, model selection, and AI cost optimization.
• Experience implementing human-in-the-loop approval workflows.
• Experience with event-driven architectures and asynchronous processing.
• Familiarity with AWS Lambda, SQS, EventBridge, or comparable cloud services.
• Experience with React, Next.js, or full-stack TypeScript applications.
• Familiarity with tRPC, Prisma, or Drizzle ORM.
• Experience with workflow automation tools such as n8n, Zapier, or Make.
• Experience developing internal tools or operational automation platforms.
• Familiarity with multi-tenant SaaS applications.
• Experience working with merchant-facing software or e-commerce platforms.
• Experience integrating healthcare, telehealth, or pharmacy-related systems.
• Understanding of healthcare data privacy and security considerations.
• Experience using AI-assisted development tools such as Cursor or Claude Code.