Job Title: Director of Enterprise Applications & Innovation

Reports to: VP of Information Technology

Direct Reports: Yes

Location: Jacksonville Office

Position type: Full-Time

FLSA Status: Exempt, Salaried

Normal Working Hours: Monday-Friday, 8:00AM-5:00PM

What You'll Do

Technology is transforming the insurance industry and at Olympus, you'll help lead what's next.

As our Director of Enterprise Applications & Innovation, you'll shape the technology strategy behind the applications our employees, agents, and customers rely on every day. You'll lead a talented development team while driving digital transformation, modern application architecture, AI adoption, and enterprise innovation across the organization.

This is more than an application development leadership role. It's an opportunity to influence how technology accelerates business growth, improves operational efficiency, and creates better experiences for employees and customers alike. If you're energized by building high-performing teams, solving complex business challenges, and bringing innovative ideas to life, this role is for you.

Key Responsibilities

Lead a High-Performing Engineering Team

Build, coach, and inspire a team of application developers while fostering a culture of collaboration, accountability, innovation, and continuous improvement. Guide software delivery from strategy through execution while maintaining high standards for quality and performance.

Shape Our Technology Future

Define the technical vision for enterprise applications, architecture, software development, and modernization initiatives. Lead the evolution of our development practices through Agile methodologies, DevOps, CI/CD, cloud technologies, and scalable engineering standards.

Drive Innovation Through AI & Automation

Identify opportunities to leverage artificial intelligence, automation, and emerging technologies to improve business processes, developer productivity, customer experience, and operational performance. Lead pilot programs, evaluate new technologies, and help bring innovative ideas into production responsibly.

Partner with Business Leaders

Serve as a strategic technology advisor to executive leadership and business partners. Translate business objectives into scalable technology solutions while balancing innovation, risk, cost, and long-term value.

Deliver Business Value

Oversee enterprise technology investments, vendor partnerships, and strategic initiatives that strengthen Olympus' technology ecosystem while ensuring projects are delivered securely, efficiently, and with measurable business impact.

What You'll Bring

• Bachelor's degree in Computer Science, Engineering, Information Systems, or a related field (Master's preferred).
• 15+ years leading enterprise application development, software engineering, or technology organizations.
• Experience building and mentoring high-performing engineering teams.
• Deep expertise in software architecture, cloud technologies, DevOps, Agile delivery, and enterprise application development.
• Experience implementing AI, automation, machine learning, or other emerging technologies in a business environment.
• Strong executive presence with the ability to influence across technical and business teams.
• Experience managing vendors, technology investments, and enterprise technology strategy.
• Strong business acumen with experience developing business cases, measuring ROI, and aligning technology investments to organizational goals.
• Insurance or financial services experience is a plus.

This position will remain open until September 10, 2026, or until a sufficient pool of qualified candidates has been identified.