Director, Strategic Initiatives & Administration | Digital Workplace & PCG Technology

Raymond James•Saint Petersburg, FL

1d•Hybrid

About The Position

Serving as a trusted advisor to senior leadership, the Director supports the development, tracking, and communication of organizational priorities and key initiatives. Working across functions, the Director helps translate strategy into action by enabling informed decision making, improving operational effectiveness, and fostering strong communication, collaboration, and stakeholder engagement throughout the organization. The Director of Strategy & Administration acts as a force multiplier driving priority, coordinating cross-functional work, managing strategic projects, and ensuring the organization runs smoothly by turning high-level goals into execution. This position requires a highly credible leader who can operate as a trusted advisor, enterprise program leader, and hands on driver of work. The successful candidate will be able to take high level direction and ambiguity and convert it into clear, structured plans that are executed consistently across the organization. They will be leading a highly performing specialized team. Additional growth and scope expansion expected.

Requirements

Minimum of 5 years of experience in a leadership or strategic role, preferably in a technology or operations environment within a large financial services organization.
Proven track record of success in strategic planning, project management, and team collaboration.
Experience working closely with senior leadership is essential.
Proven track record producing high quality executive reporting and presentations for senior audiences.
Demonstrated ability to operate effectively in ambiguous, fast moving environments while exercising sound judgment and executive level influence.
Clear understanding that this is a delivery oriented role requiring hands on execution and personal accountability for outcomes
Bachelor’s: Computer and Information Science, Bachelor’s: Information Technology, High School (HS) (Required)
General Experience – 10 to 15 years

Nice To Haves

Financial management experience including budgets, forecasting, headcount planning, and portfolio investment analysis.
Background in financial services.
The ability to perform HOV’s alongside the team and participate in presentation rotations.

Responsibilities

Collaborate with departmental leadership to define organizational strategy, set goals, and identify areas for improvement and efficiency.
Support executive decision-making through analysis, insights, and development of decision-ready materials.
Oversee project initiatives, track project outcomes, and ensure alignment with departmental objectives.
Support workforce planning, resource allocation, and budget alignment.
Drive process improvements to enhance efficiency and effectiveness across the organization.
Lead special projects and perform deep dives on priority topics as needed.
Identify opportunities to enhance operational processes and implement improvements to drive efficiency across the department.
Maintain visibility into key initiatives, risks, and progress through reporting and dashboards.
Create agendas for and provide meeting support to various leadership meetings, ensuring effective communication and alignment among stakeholders.
Own leadership operating cadence including meetings, agendas, materials, and follow-ups.
Facilitate communication and collaboration across different teams and departments to achieve shared goals.
Lead and coordinate cross-functional initiatives to ensure alignment, execution, and delivery of business value.
Lead information-gathering projects to inform strategic decisions and support the executive committee.
Develop and maintain strong relationships with key stakeholders, including internal teams and external partners.
Partner with leadership to define and operationalize strategy, translating priorities into actionable plans and measurable outcomes.
Serve as a key advisor to the SVP and executive leadership by transforming ideas, questions, and direction into structured analysis, recommendations, and actionable execution plans.
Own and drive the core operating rhythm of the organization, including leadership meetings, agendas, materials, follow ups, and executive communications.
Build, lead, and maintain a high performing HOV team, providing coaching, development, and clear accountability for results.
Drive and shape the deliverables assign to our organization from the CIO and EVP of Technology & Operations through analysis, research, and structured, data driven recommendations.
Strengthen strategic decision making by providing context, insights, scenario analysis, and trade off evaluations.
Facilitate strategic planning sessions and senior leadership workshops, including development of multi year technology priorities and combining existing roadmaps into executive level strategy.
Maintain outcomes and update on deliverables.
Prepare materials for executive committees, board level discussions, and C suite engagements.
Produce clear, concise, and decision ready reporting for senior leadership covering strategic initiatives, financial performance, execution risks, and organizational health, strategic projects.
Lead high impact initiatives assigned directly by the SVP and or Leadership team, including operating model assessments, organizational design, strategic planning enablement, and productivity transformations.
Orchestrate complex, cross functional initiatives with firm wide impact, proactively managing risks, dependencies, and executive escalations.
Partner with technology senior leaders and others across the enterprise to establish, enforce, and continuously improve product management best practices, execution standards and productivity enhancers.
Partner closely with finance, operations, and technology leaders on budget planning, forecasting, headcount management, and investment prioritization.
Support productivity and cost efficiency initiatives during periods of budget pressure while maintaining alignment to strategic objectives.
Ensure technology investment decisions are supported by rigorous financial analysis and clear linkage to enterprise priorities.
Responsible for maintaining Total Cost of Ownership deliverables with input from executive leaders.
Maintain product tracking vs headcount growth reporting analysis.