Job Title: Director of Enterprise Applications & Innovation (Application Development & AI)
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
Who We Are
Olympus Insurance Company is the premier insurance partner, providing the broadest coverage and superior service for Florida homeowners since 2007. We believe that insurance is a promise, and we honor our commitment to help homeowners navigate life's inevitable storms. Becoming an Olympian means joining a collaborative, people-first culture built on growth, accountability, and connection. Think Ahead. Think Olympus.
What Olympus Offers
We extend our signature White Glove Service to our employees through a comprehensive total rewards package, including:
- Employer-sponsored medical, dental, and vision plans
- Company-paid life insurance, short-term disability, and long-term disability
- 401(k) with company match
- Paid Time Off to include annual PTO, Holidays, Floating Holidays, and Volunteer Time Off
- Education Assistance Program and ongoing professional development opportunities
- Wellness Lunch N Learns
- Employee perks such as pet insurance, discount programs, and a welcoming office environment
At Olympus, we empower you to grow, contribute, and thrive both professionally and personally.
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.
EEO Compliance
Olympus Insurance Company is an equal opportunity employer committed to fostering a diverse, inclusive, and respectful workplace. We prohibit discrimination and harassment of any kind based on race, color, religion, national origin, sex (including pregnancy, childbirth, and related medical conditions), age, disability, genetic information, marital status, sexual orientation, gender identity or expression, veteran or military status, or any other protected characteristic under federal, state, or local law.
Agency Disclaimer:
This job posting is not intended to solicit resumes from staffing agencies. Any unsolicited resumes sent to this posting, to employees, or to the Company without a valid written and signed agreement from Human Resources will be considered the property of the Company, and no fees will be paid.
This position will remain open until September 10, 2026, or until a sufficient pool of qualified candidates has been identified.
