Executive Software Engineer Jobs in Naples, FL (NOW HIRING)

The Director Technology, Program Management is a hands-on role that will play an integral part in the Technology + Product Project Management office, focused on the creation of cross functional program/ project teams to bring order and enforce standards to the portfolio of work.

What You'll Do:

• Deliver Solutions using our delivery framework that are on time, on budget and in scope
• Create and manage projects with strong stakeholder alignment and buy-in
• Drive close project collaboration across business, technology and product
• Manage, support, and synthesize the work of project teams
• Create and update project plans, as appropriate
• Create, collaborate, and support the appropriate Project Framework documentation as required 
• Create Project Framework Gate materials as necessary
• Interface with executives to define project priorities, implementation opportunities, challenges and communicate project risks and opportunities.
• Contribute to the ongoing support of the PMO in alignment with Project Management Institute (PMI) guidelines, quality standards and company delivery framework requirements.
• Develop, implement, and govern program management processes, dashboards, templates, policies, and metrics.
• Monitor compliance with project policies and standards, including Project Status Reports and Roadmaps
• Coach and mentor project management practitioners and share knowledge of best practices.

What We're Looking For: 

• Skilled at managing teams, projects, deliverables, and timelines

• Expert-level knowledge of project and change management, methodologies, techniques, processes (e.g., Project and Portfolio Management Methodology - PPM).

• Vendor management experience

• Expert with Jira and Confluence and KPI generation from Jira

• Expert working knowledge of Microsoft Office Suite

• Knowledge of resource management tools.

• 7+ years' experience in full life cycle of complex software deployment projects

• Must be a self-starter that takes initiative in development of project teams and schedules with cross functional teams. 

• Excellent judgment with proven ability to identify problems and deal with complex issues.

• Strong analytical and problem-solving skills, particularly on challenging, complex, and difficult issues to develop solutions that address root causes.

• Cross-Team Dependencies: Orchestrate and track dependency frameworks across multiple product lines and platforms to prevent bottlenecks and reduce waiting times

• Communication: Exceptional storytelling and conflict-resolution skills, capable of influencing C-suite executives and managing cross-functional matrix environments

• Lead the annual and quarterly Objective and Key Results (OKR) and Quarterly Business Review (QBR) processes. Ensure company goals cascade clearly to teams and reflect true capacity and sequencing.

• Road mapping: Develop comprehensive portfolio roadmaps that balance short-term deliverables with long-term strategic investments.

• Resource Capacity Planning: Align departmental capacity limits with strategic project needs to ensure teams are properly funded and staffed.

• Trade-off Facilitation: Host portfolio forums for prioritization and dependency alignment. Make difficult trade-offs explicit and adjust sequencing based on resource realities.

• Prioritization Models: Establish strict scoring models and gating processes to evaluate new project requests based on strategic alignment, ROI, and risk

• Performance Monitoring: Define, track, and publish portfolio KPIs via executive-ready dashboards

• Financial Acumen: Strong understanding of financial forecasting, budget management, and return-on-investment (ROI) tracking.

Required Qualifications

• Bachelor's degree in Business, Engineering, Information Technology, or a related field.

• Project Management Institute Certifications in Program/Project Management or Equivalent 

• Minimum of 10+ years of project management experience, including ownership of large, complex, or enterprise-wide initiatives.

• Demonstrated success leading cross-functional teams and managing multiple stakeholders in fast-paced environments.

• Strong knowledge of project management methodologies, including Agile, Waterfall, or hybrid delivery models.

• Expert in managing project budgets, schedules, risk registers, and status reporting.

• Excellent written and verbal communication skills, including executive-level presentations and stakeholder management.

• Expert proficiency with common project management tools such as Microsoft Project, Jira, and similar platforms.

The starting salary is $165k with annual bonus and profit-sharing eligibility; actual salary will be determined based on years of relevant work experience. 

What You'll Get:

• 40% off any standard Hertz Rental 
• Paid Time Off
• Medical, Dental & Vision plan options
• Retirement programs, including 401(k) employer matching
• Paid Parental Leave & Adoption Assistance
• Employee Assistance Program for employees & family
• Educational Reimbursement & Discounts
• Voluntary Insurance Programs - Pet, Legal/Identity Theft, Critical Illness
• Perks & Discounts -Theme Park Tickets, Gym Discounts & more