Director of IT Project Management

Join to apply for the Director of IT Project Management role at Olympus Insurance Company
.

• Job Title
  :
  Director of IT Project Management
• Reports To
  :
  Chief Information Officer (CIO)
• Location
  :
  Jacksonville Office (on-site)
• Position Type
  :
  Full Time
• FLSA Status
  :
  Exempt

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 vibrant and encouraging team where you can be a part of delivering the insurance experience that people deserve.

Think Ahead. Think Olympus.

• Employer-sponsored medical, dental, and vision plans, along with company-paid life insurance and short- and long-term disability coverage.
• 401K plan with up to 4% company match.
• Pet insurance, company discount programs, and opportunities for educational and professional development.
• Paid time off, paid holidays, welcoming employee breakroom, and other perks to support your health, happiness, and career growth.

Olympus Insurance is seeking a strategic and results-driven Director of IT Project Management to build and lead our Project Management Office (PMO). As Director of IT Project Management, you will lead Olympus' IT project execution from strategy to realization, establishing and evolving the PMO into a business-critical function that drives efficiency, ensures alignment with company goals, and measures the impact of key technology initiatives.

• Establish and lead the PMO: develop and institutionalize project management standards, frameworks, tools, and templates across the enterprise.
• Strategic alignment: partner with the CIO and senior leaders to ensure projects align with business strategy, regulatory requirements, and long-term technology goals.
• Portfolio oversight: oversee the IT project portfolio, ensuring effective prioritization, resource allocation, and risk management.
• Governance and reporting: develop and lead steering committees, providing transparent communication on project status, risks, dependencies, and value realization.
• Support enterprise data strategy initiatives that improve decision‑making and operational efficiency.
• Methodology leadership: apply and adapt the most suitable project management approach (traditional, Agile, hybrid) to achieve desired outcomes efficiently.
• Executive and sponsor guidance: guide project sponsors through cost‑benefit analysis and ROI evaluation to ensure projects are properly justified and aligned with business priorities.
• Project realization management: monitor and assess project outcomes after completion and implementation, ensuring benefits are realized, measured, and reported against original objectives.
• Technology & tools management: utilize and oversee enterprise project management tools such as Smartsheet, Microsoft Project, Jira, and other collaboration platforms to enable effective planning, tracking, and reporting.
• Mentorship and development: lead, coach, and develop a team of project managers and analysts to ensure consistent, high‑quality execution and professional growth.
• Continuous improvement: monitor and refine project management processes to enhance performance, predictability, and organizational maturity.
• Budget & financial stewardship: collaborate with the CIO and Finance to manage the IT capital and operational budgets, providing cost forecasts and ROI analysis.
• Monitor financial performance of the IT project portfolio, ensuring fiscal discipline and alignment with Olympus’ annual planning cycles.

• Bachelor’s degree in Business, Information Technology, or related field.
• PMP certification (or equivalent recognized project management credential).
• 5+ years leading enterprise IT project portfolios or managing a PMO.
• Demonstrated experience using Smartsheet, Microsoft Project, and Jira.
• Proven ability to influence C‑suite executives and lead steering committees.
• Strong financial acumen: cost‑benefit analysis, ROI assessments, and post‑implementation reviews.
• Expertise…