Olympus Insurance Company
Director of IT Project Management
Olympus Insurance Company, Jacksonville, Florida, United States, 32290
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
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 vibrant and encouraging team where you can be a part of delivering the insurance experience that people deserve. Think Ahead. Think Olympus.
What Olympus Offers At Olympus our White-Glove service extends to our team members! We offer employer-sponsored medical, dental, and vision plans, along with company-paid life insurance and short- and long-term disability coverage. Secure your future with our 401K plan that includes up to 4% company match.
Enjoy a welcoming employee breakroom, paid time off, paid holidays, pet insurance, company discount programs, and opportunities for educational and professional development. With many additional perks, we’re committed to supporting your health, happiness, and career growth!
What You’ll Do Olympus Insurance is seeking a strategic and results‑driven Director of IT Project Management to build and lead our Project Management Office (PMO). If you're passionate about aligning technology with business strategy and love turning vision into measurable outcomes, we want to hear from you.
As Director of IT Project Management, you will lead Olympus' IT project execution from strategy to realization. You'll establish and evolve the PMO into a business‑critical function that drives efficiency, ensures alignment with company goals, and measures the impact of key technology initiatives. This is a hands‑on leadership role where you'll be able to help shape a future‑focused IT environment while delivering real business results. Join a collaborative team that values innovation, leadership, and professional growth.
Key Responsibilities
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, whether traditional, Agile, hybrid, or otherwise 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.
What You Bring Required
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 in both traditional and Agile/hybrid project management methodologies
Preferred
Master’s degree in Business, IT, or related field
Additional certifications (PMI‑ACP, SAFe, PRINCE2)
Experience in insurance, financial services, or other regulated industries
Knowledge of property and casualty insurance operations and systems
EEO Compliance Olympus Insurance Company is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based upon race, religion, color, national origin, sex, age, sexual orientation, gender identity, status of an individual with a disability, veteran status or any other characteristics protected by federal, state or local law.
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Director of IT Project Management Reports To:
Chief Information Officer (CIO) Location:
Jacksonville Office (on-site) Position type:
Full Time FLSA Status:
Exempt
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 vibrant and encouraging team where you can be a part of delivering the insurance experience that people deserve. Think Ahead. Think Olympus.
What Olympus Offers At Olympus our White-Glove service extends to our team members! We offer employer-sponsored medical, dental, and vision plans, along with company-paid life insurance and short- and long-term disability coverage. Secure your future with our 401K plan that includes up to 4% company match.
Enjoy a welcoming employee breakroom, paid time off, paid holidays, pet insurance, company discount programs, and opportunities for educational and professional development. With many additional perks, we’re committed to supporting your health, happiness, and career growth!
What You’ll Do Olympus Insurance is seeking a strategic and results‑driven Director of IT Project Management to build and lead our Project Management Office (PMO). If you're passionate about aligning technology with business strategy and love turning vision into measurable outcomes, we want to hear from you.
As Director of IT Project Management, you will lead Olympus' IT project execution from strategy to realization. You'll establish and evolve the PMO into a business‑critical function that drives efficiency, ensures alignment with company goals, and measures the impact of key technology initiatives. This is a hands‑on leadership role where you'll be able to help shape a future‑focused IT environment while delivering real business results. Join a collaborative team that values innovation, leadership, and professional growth.
Key Responsibilities
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, whether traditional, Agile, hybrid, or otherwise 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.
What You Bring Required
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 in both traditional and Agile/hybrid project management methodologies
Preferred
Master’s degree in Business, IT, or related field
Additional certifications (PMI‑ACP, SAFe, PRINCE2)
Experience in insurance, financial services, or other regulated industries
Knowledge of property and casualty insurance operations and systems
EEO Compliance Olympus Insurance Company is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based upon race, religion, color, national origin, sex, age, sexual orientation, gender identity, status of an individual with a disability, veteran status or any other characteristics protected by federal, state or local law.
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