Project Manager 1099 Jobs in Florida (NOW HIRING)

Service Beyond Banking- At Gulf Winds, we are forward-thinking and team-oriented. We recognize and reward service that exceeds our members’ expectations and, most importantly, have fun while working hard and impacting our community. We’re looking for driven professionals who are passionate about service, fueled by purpose, and guided by core values of Integrity, Care, Growth, and Innovation

We own our decisions and actions by doing the right thing, learning from our mistakes, and taking responsibility.

We help members meet their goals by listening to understand and offering the best solutions, placing kindness above all else.

We set ambitious goals, provide personal development opportunities, and encourage results.

We challenge the status quo to enhance the member’s experience and solve tomorrow’s challenges today.

We offer a comprehensive benefits package designed to support your health, financial well-being, and work-life balance. Benefits include 11.5 paid federal holidays, PTO starting at 18 days for new hires, 16 hours of paid volunteer time, competitively priced medical insurance, and dental and vision coverage with 100% of individual premiums paid by Gulf Winds. Team members also receive employer-paid life insurance, short-term disability coverage, a 401(k) with company match, an employer-funded pension plan, flexible spending accounts, tuition reimbursement, and wellness programs.

Working at Gulf Winds is not just a job, it’s a career. We’re hiring collaborative, motivated people who want to love what they do. We recognize and reward excellent member service and have fun while working hard. When you join the team, you can expect:

• Open and transparent communication with your leaders
• Consistent coaching and opportunities to improve performance
• Collaborative and team-focused environments
• Short and long-term professional development
• Opportunity to participate in cross-functional projects

With you on our team we can achieve our vision of becoming the leading and most trusted credit union on the Gulf Coast.

The Senior Project Manager is responsible for leading, planning, organizing, and executing complex, multi'departmental, and enterprise'wide initiatives with significant technical integration and organizational impact. Operating with a high degree of independence, this role establishes the delivery strategy, drives project execution through all phases of the lifecycle (initiation, planning, execution, control, and closure), and ensures solutions meet business, technical, regulatory, and quality requirements. The Senior Project Manager proactively identifies risks and interdependencies, facilitates cross'functional collaboration, provides executive'level communication, and ensures the successful transition of solutions into operational readiness. This role also mentors project managers and analysts, contributes to continuous improvement of project management practices, and partners with leadership to ensure alignment with enterprise strategy.

• 30% Leads the full project lifecycle for large, complex, or enterprise wide initiatives involving multiple departments, systems, and vendors. Defines execution approach, develops integrated schedules, manages scope and budget, ensures adherence to methodology, and drives day to day execution to achieve measurable outcomes.
• 25% Facilitates coordination between business units, IT, vendors, and analysts to ensure technical requirements, integrations, dependencies, and constraints are understood and addressed. Leads detailed working sessions, technical reviews, and decision forums to ensure alignment between business needs and system capabilities.
• 15% Identifies, evaluates, and manages risks, issues, and interdependencies across multiple projects and systems. Develops mitigation strategies, performs impact assessments, escalates critical items early, and ensures transparent, data-driven decision-making with leaders and stakeholders.
• 10% Provides clear, concise, executive ready communication, including dashboards, status summaries, risk profiles, and program updates. Facilitates decision making sessions and ensures leadership is informed of project progress, challenges, and required actions.
• 10% Mentors Project Managers and Technical Business Analysts; provides feedback on documentation, execution practices, and communication quality. Contributes to improving standards, templates, workflows, reporting structures, and tools to increase project delivery maturity across the organization.
• 5% Partners with Finance and Risk Management to develop budgets, track forecasts, manage SOWs, and oversee vendor delivery performance. Holds vendors accountable for outcomes, escalates deficiencies, and ensures contractual compliance within projects.
• 5% Performs other job related duties as assigned.

1. 1. Strategic Delivery: Enterprise critical initiatives are delivered on time, within budget, and within scope, with documented benefits realization and minimal production disruption.
2. 2. Executive Engagement: ELT and key stakeholders receive timely, decision-ready updates; issues and risks are escalated early with clear options and recommendations.
3. 3. Portfolio Effectiveness: Interdependencies and resource/contention risks are identified early and reduced through proactive planning; cross-team cycle times improve relative to the baseline.
4. 4. Team Leadership: Provides high-quality mentorship, elevates the performance of Project Managers/Analysts, and fosters a culture of accountability and continuous improvement.
5. 5. Technical Execution: Complex, multi-system implementations (e.g., core, digital channels, integrations) are sequenced and delivered with strong UAT readiness and cutover plans.
6. 6. Vendor Performance: Third-party providers meet contractual obligations and SLAs; performance issues are addressed with corrective actions and measurable outcomes.
7. 7. Reporting Quality: Portfolio and project status are accurately maintained in the prescribed PM tools and repositories; dashboards and reports are complete, accurate, and timely.
8. 8. Compliance & Policy Adherence: Complies with all applicable rules, regulations, procedures, and policies, including but not limited to BSA, OFAC, and Physical Security.

Experience 5'7+ years of project management experience, including leading high-risk, multi-stakeholder technical projects; financial services or other regulated industries preferred. Demonstrated success delivering multi'system implementations and integrations; experience coordinating across business units, IT, vendors, and analysts. Symitar Core and related systems experience preferred (or equivalent core banking environment).

Education (1)A bachelor's degree is strongly preferred.

(2)PMP is required.

(3)IT-Focused Certifications preferred. Preferably related to ITIL, Azure, or AI/ML fundamentals.

Interpersonal Skills Executive-level communication and facilitation; able to influence without authority across departments. Advanced conflict resolution in high-stakes environments; skilled at guiding data-driven decisions and balancing business/technical tradeoffs. Strong analytical, technical, and organizational skills; exceptional documentation and presentation abilities. Demonstrates analytical, technical, and organizational skills. Must have excellent documentation and verbal and written communication/presentation skills. The ability to manage many activities and assignments, recognize when prioritization may be needed, and escalation appropriately.

Other Skills Advanced proficiency with Microsoft Project, Excel, Word, PowerPoint, and Power BI; accustomed to portfolio and project management in Jira or MS Project.

Familiarity with software implementation lifecycles, configuration management, QA/UAT practices, and technical documentation; able to translate between business and technical stakeholders.

Financial acumen (budgeting, forecasting, cost/benefit, ROI modeling) and vendor/SOW management.

This role requires sitting at a computer for most of the day. This role would also need the ability to file files, open filing cabinets, and bend or stand as necessary. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential function.

The position is based in-office in our Pensacola, Florida market, operates primarily in an office setting, and routinely uses standard office equipment, including computers, printers, and phones. This position requires consistent in-office presence to collaborate with team members and fulfill job responsibilities effectively. It requires actively participating in conference calls and meetings with other Credit Union team members and vendors. The standard expected work schedule is Monday through Friday, 8:30 a.m. to 5:00 p.m. After-hours work or travel is required to meet project deadlines or attend conferences, seminars, or meetings. Must adhere to safety rules and regulations.

This Job Description is not a complete statement of all duties and responsibilities comprising the position.