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

Job Description Summary

Note: This position follows our hybrid-friendly schedule, so you get the best of both worlds – flexibility and collaboration. In office days will be 2-3 per week averaging 10-12 days per month in our St Petersburg, FL Corporate Office.
This role is not eligible for Work Visa sponsorship, either currently or in the future.

Job Description

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.

Essential Duties and Responsibilities:

• Strategic Planning and Prioritization: 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.

• Project Management and Tracking: 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.

• Operational Efficiency: 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.

• Meeting Support and Coordination: 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.

• Cross-Functional Collaboration: 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.

• Information Gathering and Analysis: Lead information-gathering projects to inform strategic decisions and support the executive committee. 

• Stakeholder Engagement: 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.

Success in this role will be demonstrated by:

• Predictable execution and improved outcomes across strategic initiatives.

• Clear alignment between technology strategy, investment priorities, and delivery.

• High quality, decision ready executive reporting adopted by senior leadership.

• Consistent feedback from leadership, recognizing the Director as a trusted partner who reduces organizational burden by not only coordinating work, but personally executing critical deliverables, demonstrating a strong ‘player-coach’ mindset and the ability to drive outcomes independently when team capacity is limited.

• Strong operating discipline and cadence across the technology leadership team.

• Strengthen Collaboration, Communication, and Stakeholder Engagement.

Skills / Previous Experience: 

Required: 

• 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

Preferred:

• 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.

Knowledge and Abilities:

• Strategic Thinking: Ability to develop and implement strategic plans that align with organizational objectives.

• Operational Leadership: Experience in managing day-to-day operations and driving efficiency improvements.

• Communication Skills: Excellent written and verbal communication skills to effectively engage with diverse stakeholders. 

• Project Management: Proven ability to manage multiple projects simultaneously and track outcomes.

• Collaboration and Influence: Strong interpersonal skills to build and maintain relationships across the organization. 

Leadership:

• 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.

Technology Strategy and Advisory Support:

• 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. 

Executive Reporting & Communication:

• 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.

Administration & Special Project Execution:

• 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.

Financial and Productivity Support:

• 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.

Licenses/Certifications:

• None required.

Education

Bachelor’s: Computer and Information Science, Bachelor’s: Information Technology, High School (HS) (Required)

Work Experience

General Experience – 10 to 15 years

Certifications

Travel

Less than 25%

Workstyle

Hybrid

The total compensation for this position includes base salary or wages, and may include components such as additional compensation (cash or equity), discretionary bonuses, or commissions. This position is eligible for a benefits package that may include medical, dental, and vision; life insurance; critical illness insurance and accident insurance; disability benefits; retirement savings; paid time off (including vacation, holidays, and sick leave); and parental leave.  Eligibility for benefits and specific offerings may vary based on position and employment status. To view more details of the benefits offered, visit Myrjbenefits.com.

At Raymond James our associates use five guiding behaviors (Develop, Collaborate, Decide, Deliver, Improve) to deliver on the firm's core values of client-first, integrity, independence and a conservative, long-term view. 
We expect our associates at all levels to:
•  Grow professionally and inspire others to do the same
•  Work with and through others to achieve desired outcomes
•  Make prompt, pragmatic choices and act with the client in mind
•  Take ownership and hold themselves and others accountable for delivering results that matter
•  Contribute to the continuous evolution of the firm

At Raymond James – as part of our people-first culture, we honor, value, and respect the uniqueness, experiences, and backgrounds of all of our Associates.  When associates bring their best authentic selves, our organization, clients, and communities thrive. The Company is an equal opportunity employer and makes all employment decisions on the basis of merit and business needs. 

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