Lead Software Engineer

Churchstreeter & Crosse is hiring a Lead Software Engineer, AI & Platform to advance its proprietary healthcare talent technology SaaS platform. The role combines hands-on software architecture and development, production AI capabilities, enterprise integrations, and coordination of distributed engineering teams, while ensuring security, scalability, and maintainability.

Responsibilities:

• Platform Architecture & Development: Translate product vision into technical architecture, specifications, milestones, and executable engineering plans; personally design, write, debug, and improve production SaaS code
• AI Engineering: Lead the design and implementation of production AI capabilities, including RAG, embeddings, tool calling, structured outputs, agentic workflows, evaluation, guardrails, and human oversight
• Enterprise Integrations: Architect reliable integrations using APIs, webhooks, authentication, asynchronous processing, data synchronization, monitoring, and failure recovery
• Distributed Engineering Leadership: Coordinate U.S.-based and international engineers, contractors, and partners; assign workstreams, manage dependencies, set acceptance criteria, and establish effective cross-time-zone handoffs
• Technical Quality & Accountability: Review architecture and code from internal and external contributors; establish standards for testing, documentation, deployment, security, and maintainability; hold partners accountable for delivery
• Engineering Operations: Implement CI/CD, automated testing, observability, logging, monitoring, and effective technical documentation and knowledge transfer
• Security & Risk Management: Identify technical debt, scalability limits, integration risks, and security or privacy concerns early; incorporate reliability, governance, and protection of sensitive data throughout the platform
• Product & Executive Collaboration: Partner with product, business, and executive stakeholders to evaluate tradeoffs, communicate progress and blockers, and align technical delivery with the product roadmap
• Technical Ownership & Mentorship: Mentor engineers while remaining hands-on; ensure critical code, documentation, institutional knowledge, and intellectual property remain under Churchstreeter & Crosse’s control

Requirements:

• 8+ years of progressive professional software engineering experience, including meaningful Senior, Lead, Staff, Principal, or comparable engineering responsibilities
• Demonstrated success architecting, building, launching, and scaling production SaaS applications, with current hands-on coding and debugging capability
• Experience leading technical execution across distributed, international, and contracted engineering teams while personally contributing production code
• Strong backend architecture, API, database, cloud infrastructure, and modern software design experience
• Production experience building AI-enabled applications, with working knowledge of LLMs, RAG, vector retrieval, agentic workflows, AI evaluation, observability, and model tradeoffs
• Experience implementing complex enterprise integrations and designing for resilience, security, monitoring, and recovery
• Experience establishing code review, architecture, testing, CI/CD, documentation, security, and operational quality standards
• Ability to turn product requirements into technical plans, assess risks and technical debt, and communicate effectively with business and executive stakeholders
• Enterprise B2B or multi-tenant SaaS; healthcare, HR, talent acquisition, workforce or people analytics technology; HCM/HRIS platforms; Workday, Phenom, Infor, Oracle, SAP SuccessFactors or similar integrations; high-volume integrations; sensitive employee, candidate, or healthcare data; data-intensive analytics; AI workflow automation; and assuming ownership of software built by external partners
• Bachelor's degree in Computer Science, Software Engineering, Computer Engineering, AI, Machine Learning, Data Science, or a related technical field preferred
• Advanced degrees and relevant cloud, cybersecurity, or AI certifications are valued; demonstrated engineering ability remains essential