Director, Software Technology Delivery

Position Summary

We are looking for a Director of Technology Delivery who is both dynamic and experienced. This role is crucial in steering our internal IT team and vendor partners, ensuring the development and support of software applications and integrations are reliable, high‑quality, and predictable through a well‑managed agile SDLC process. The Delivery Lead will collaborate closely with business leadership, vendor partners, and internal technology teams to deliver timely solutions that align with our business goals.

• Strategic Leadership: Define and lead IT strategies that add value to the business.
• Financial Management: Oversee budgeting, expenses, and personnel.
• Relationship Building: Foster strong connections with Ryan Alternative Risk business leaders.
• Project Oversight: Manage the quantification, delivery, and testing of development efforts on a regular sprint cycle.
• Collaboration: Work with IT department leaders and Ryan Specialty’s vendors in design, scoping, support, and troubleshooting.
• Communication: Utilize collaborative communication and project management platforms for transparency.
• Change Management: Drive user adoption of new applications and technologies.
• Innovation: Stay abreast of the latest insurance‑industry related technological advancements for potential adoption.
• Resource Coordination: Organize internal and external resources for project execution.
• Reporting: Prepare and present monthly status reviews and quarterly business reviews.

• Unqork: For intake automation and task management
• Ruby on Rails: An underwriting workbench based on Ruby on Rails
• Coherent Spark: For rater integration
• Vertafore's IMS: For back‑office management
• Insurity’s SureMGA: For policy administration
• Azure: For cloud management

• Education: Bachelor’s degree in computer science or information technology.
• Experience: 10+ years in software development and delivery.
• Insurance Expertise: 10+ years in insurance process automation, preferably with a focus on Property and Casualty.
• Project and Program
  
  Experience:
  
  10+ years driving or overseeing project or program management.
• Leadership: 5+ years in personnel and team management.
• Development Processes: Deep understanding of modern development processes including requirements, visualizations, prototyping, Agile, and SDLC.

• Innovation: Be at the forefront of a major technology transformation.
• Leadership: Lead a talented team of IT professionals and vendors.
• Automation: Drive innovation using Generative AI to automate workflows.
• Collaboration: Work with business leaders to deliver impactful solutions.

On‑site in Chicago, IL. Salary range $140,000 – $175,000 annually; eligible for bonuses and benefits.

We offer paid time off for company holidays, vacation, sick and personal days, paid parental leave, mental health services, and more. Visit  for full details.

Ryan Specialty is an Equal Opportunity Employer. We are committed to building and sustaining a diverse workforce throughout the organization and fostering an inclusive workplace where all employees are valued. Applicants must be authorized to work for any employer in the U.S.; we are unable to sponsor or take over sponsorship of an employment visa at this time.

We provide reasonable accommodations to individuals with disabilities to participate in the application or interview process. Contact  to request an accommodation.