Director of Engineering

Position Summary

We are seeking a technically strong and experienced Director of Software Development to lead our engineering teams in building Raintree’s next-generation platform. Reporting directly to the VP of Engineering, this hands-on leadership role is responsible for guiding architectural strategy, overseeing complex development initiatives, and mentoring teams to deliver high-quality, scalable, and secure solutions aligned with business goals. The Director will play a critical role in shaping platform evolution and will collaborate closely with the Raintree leadership team to ensure the right talent and structure are in place to execute the development roadmap with excellence.

Responsibilities

• Technical Leadership & Architecture
• Provide hands-on leadership across the full software development lifecycle (SDLC): architecture, design, implementation, deployment, and support
• Architect and design complex, high-performance systems with an emphasis on scalability, availability, and security
• Stay current with emerging technologies and evaluate their potential to enhance product capabilities and engineering efficiency
• Engineering Excellence
• Establish and drive best-in-class engineering standards, processes, and coding practices
• Ensure adherence to performance, scalability, and security guidelines throughout the development process
• Champion innovation by identifying and integrating new ideas, tools, and capabilities that align with business and platform objectives
• Team Leadership & Collaboration
• Lead, mentor, and develop engineering talent through coaching, feedback, and career development planning
• Collaborate cross-functionally with product management and other departments to define technical requirements and deliver high-quality solutions on time and within scope

Skills and Qualifications

• Deep understanding of modern software architectures, including Microservices, TypeScript, React, and AWS
• Strong expertise in software architecture, design patterns, cloud infrastructure (AWS), and DevOps best practices
• Demonstrated success in delivering complex, high-scale, and mission-critical systems
• Proven experience leading and scaling engineering teams within Agile environments (Scrum, Lean, Kanban)
• Experience managing vendor relationships and implementing effective offshore development strategies
• Exceptional leadership, collaboration, and communication skills, with the ability to align cross-functional teams around strategic goals

Preferred:

• Hands-on experience with microservices architecture, containerization technologies (Docker, Kubernetes), and CI/CD pipelines
• Strong background in SaaS, enterprise platforms, and high-availability, mission-critical systems
• Familiarity with regulatory and security frameworks, including HIPAA, OWASP, and industry standards such as NIST and CIS

Education and Experience

Required:

• Bachelor’s or Master’s degree in Computer Science, Engineering, or related field.
• 6+ years of software development experience, with 3+ years in a leadership or management role.
• 5+ years experience developing SaaS cloud based applications