Senior Director of Software Architecture and Development

Role Description

Imagine360 is seeking a Sr. Director of Software Development to join the team! The Sr. Director of Software Development is a strategic leadership role responsible for driving the design, development, and implementation of innovative and scalable software solutions.

This visionary and results-driven leader in our engineering organization will be responsible for defining our long-term technical strategy, scaling multiple high-performing engineering teams, and overseeing the delivery of mission-critical software solutions. As a key technology leader, you will partner closely with product management, operations, and executive leadership to align technical roadmap milestones with our core business objectives.

Position Location: 100% remote

• Strategic Leadership: Define and execute a scalable software engineering strategy that drives operational excellence and long-term business growth.
• Team Management: Oversee, mentor, and grow multiple cross-functional engineering teams, including engineering managers and directors.
• Product Delivery: Own the end-to-end software development lifecycle, ensuring high-quality, reliable code is delivered on time.
• Architecture Oversight: Champion modern, scalable architectures, cloud infrastructure deployment, and data privacy initiatives.
• Process Optimization: Implement and refine Agile/Scrum development methodologies, CI/CD pipelines, and automated testing frameworks to improve velocity.
• Legacy Modernization: Champion the evolution of existing codebases, driving the deliberate migration of legacy frameworks into modern, decoupled microservices.
• AI Tooling Adoption: Drive the integration of AI-assisted engineering practices, automated tooling, and intelligent code assistants to boost team productivity.
• Financial Oversight: Manage departmental budgeting, resource allocation, vendor contracts, and tool monetization costs.
• Cross-Functional Collaboration: Partner with Product, Security, and Operations to resolve complex technical dependencies and cross-departmental bottlenecks.
• Collaboration: Build and maintain strong relationships with key stakeholders across the organization, including business leaders, product managers, and internal teams.
• Other duties as assigned.

Qualifications

• Bachelor's degree in Computer Science, Software Engineering, or a highly related technical field (Master's or MBA preferred).
• 10+ years of professional software engineering experience delivering customer-facing web and mobile applications.
• 5+ years of experience in senior engineering leadership roles, specifically managing managers or multiple complex platform portfolios.

Requirements

• Strong experience with cloud platforms (AWS, Azure, or GCP), modern microservice architectures, and relational/NoSQL databases.
• Expert-level knowledge of DevOps, automated testing paradigms, compliance standards, and product engineering operations.
• Superior communication and negotiation skills, with a proven ability to translate complex technical jargon for executive-level audiences.
• Proven experience leading and managing development teams.
• Healthcare industry / HIPAA regulated data environment experience preferred.
• Experience working in highly regulated, operationally critical, or financially sensitive software environments.
• Demonstrated success migrating legacy monolithic infrastructures into distributed, microservice environments.
• Active participation or leadership within local or global technology communities.

Benefits

• Multiple Health plan options
• Company paid employee premiums for disability and life insurance
• Parental Leave Policy
• 20 days PTO to start / 10 Paid Holidays
• Tuition reimbursement
• 401k Company contribution
• Company paid Short & Long term Disability plus Life Insurance
• Professional development initiatives / continuous learning opportunities
• Opportunities to participate in and support the company's diversity and inclusion initiatives

Company Description

Imagine360 is a health plan solution company that combines 50+ years of self-funding healthcare expertise. Over the years, we've helped thousands of employers save billions on healthcare. Our breakthrough total health plan solution is fixing today's one-size-fits-none PPO insurance problems with powerful, customized, member-focused solutions.

Imagine360 is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.

RECRUITMENT AGENCIES PLEASE NOTE: Imagine360 will only accept applications from agencies/business partners that have been invited to work on a specific role. Candidate Resumes/CV's submitted without permission or directly to Hiring Managers will be considered unsolicited and no fee will be payable. Thank you for your cooperation.