Senior IT Project Manager

Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers.

Brown & Brown is seeking a Senior IT Project Manager to lead business-led technology transformation initiatives across our Retail organization. This role is responsible for end‑to‑end delivery of large‑scale IT projects, serving as the single point of accountability for execution, risk, financial management, and stakeholder alignment.

The ideal candidate is experienced working with Managing Directors and executive leaders as stakeholders, serving as the primary point of accountability for delivery, risk management, and clear, decision‑ready communication.

How you will Contribute:

Enterprise‑Scale IT Project Leadership

• Lead highly complex, cross‑functional IT initiatives with multiple workstreams and significant business impact.
• Manage concurrent initiatives with broad scope, complex dependencies, and enterprise‑level visibility.
• Own end‑to‑end delivery accountability for scope, schedule, cost, risk, quality, and outcomes across initiatives typically ranging from $1M–$10M.
• Translate business objectives into actionable technology delivery plans, coordinating architecture, engineering, infrastructure, data, security, and vendor teams.
• Select and apply Agile, Waterfall, or hybrid delivery approaches aligned to initiative complexity, risk, and organizational readiness.

Senior Stakeholder & Governance Management

• Serve as the strategic delivery partner for Managing Directors and senior technology leadership.
• Lead executive‑level governance forums, steering committees, and status reviews for initiatives with high organizational impact and risk exposure.
• Proactively manage inter‑project and inter‑portfolio dependencies, escalations, and delivery trade‑offs.
• Communicate with clarity and authority, framing technical progress, risks, and decisions in business terms.

Technology Delivery & Resource Orchestration

• Coordinate delivery across teams of 15–50+ resources, including internal staff, contractors, and external partners.
• Manage vendor performance, delivery quality, and contractual expectations.
• Ensure alignment with enterprise architecture, security, and operational standards.
• Balance transformation delivery with production stability and operational risk management.
• Operate effectively in ambiguous, fast-evolving environments, bringing structure, clarity, and momentum to complex delivery challenges.

Financial & Risk Stewardship

• Own financial management ensuring investments align to ROI, business outcomes, and strategic priorities for large‑scale technology initiatives, including forecasting, tracking, and variance management within $1M–$10M budgets.
• Identify, assess, and mitigate delivery risks across multi‑vendor, multi‑team environments.
• Develop mitigation and contingency plans before risks materially impact delivery, cost, or business outcomes.
• Ensure delivery decisions protect business value, compliance, and return on investment.

Leadership & Mentorship

• Set expectations and model behaviors for senior‑level project management excellence.
• Mentor and support less‑senior project managers through guidance on complex delivery scenarios, risk management, and stakeholder engagement.
• Contribute to the evolution of delivery standards, governance models, and portfolio reporting across Retail Technology.

Skills and Experience to be Successful:

• Bachelor’s degree in Business, Information Systems, Computer Science, or related field.
• 5–8+ years of experience leading large, complex IT projects or programs.
• Demonstrated experience managing:
• $1M+ technology budgets
• Multi‑team, cross‑functional delivery environments
• Senior and executive‑level stakeholders
• Strong background in technology delivery, system integration, and platform‑based initiatives.
• Proficiency with project and portfolio management tools (e.g., Smartsheet, Azure DevOps, PPM platforms).
• Exceptional communication skills, including executive‑level storytelling and decision framing.
• Able to travel up to 30%.
• PMP, PgMP, SAFe, or equivalent certification. Preferred
• Experience in insurance, financial services, or highly regulated environments. Preferred
• Experience delivering CRM, data, platform modernization, or enterprise integration initiatives. Preferred

Teammate Benefits & Total Well-Being

We go beyond standard benefits, focusing on the total well-being of our teammates, including:

• Health Benefits: Medical/Rx, Dental, Vision, Life Insurance, Disability Insurance
• Financial Benefits: ESPP; 401k; Student Loan Assistance; Tuition Reimbursement
• Mental Health & Wellness: Free Mental Health & Enhanced Advocacy Services
• Beyond Benefits: Paid Time Off, Holidays, Preferred Partner Discounts and more.

Not reflective of all benefits. Enrollment waiting periods or eligibility criteria may apply to certain benefits. Benefit details and offerings may vary for subsidiary entities or in specific geographic locations.

Recruiting Vendor Disclosure Statement

Brown & Brown does not accept unsolicited resumes from external recruiters, recruitment vendors or employment agencies ("Recruiting Vendors"). Recruiting Vendors must have a valid written agreement and received prior written authorization from an authorized Brown & Brown representative before submitting candidates for any publicly posted role. Any unsolicited resumes submitted to Brown & Brown or its employees become the property of Brown & Brown, and no fees will be paid for such submissions. Additional information regarding this policy can be found on our careers page.

The Power To Be Yourself

As an Equal Opportunity Employer, we are committed to fostering an inclusive environment comprised of people from all backgrounds, with a variety of experiences and perspectives, guided by our Diversity, Inclusion & Belonging (DIB) motto, “The Power to Be Yourself”.