Associate Chief of Staff - Apprenticeship - Onsite Tampa

The Baldwin Group • Tampa, FL

14d • Onsite

About The Position

The Associate Chief of Staff Apprenticeship is an early-career role offering direct exposure to executive leadership, enterprise strategy, and operational execution at The Baldwin Group. The colleague works alongside the CEO, Chief of Staff, Executive Leadership Team, and Operating Segment Presidents, supporting key business processes and coordination across functions while learning about business transformation, executive decision-making, leadership dynamics, and cross-functional collaboration. The position is based in the Tampa office, five days per week.

The role supports executive meeting preparation and follow-through for the Office of the CEO, as well as active enterprise transformation initiatives in coordination with the Business Transformation portfolio and the Office of the Chief of Staff. It may involve off-hour events and time-sensitive matters requiring immediate attention or support.

Requirements

• A recent master's graduate, an early-career professional 2–4 years out of undergraduate study, or a Junior Military Leader.
• Strategic mindset and strong analytical skills.
• Proactive problem-solving ability and comfort in fast-paced, high-visibility environments.
• Exceptional attention to detail and ability to ensure accuracy and alignment in deliverables.
• Ability to manage competing priorities across multiple stakeholders and move between operational and strategic work.
• Excellent written and verbal communication skills, including the ability to distill complex information into actionable insights and influence senior stakeholders using a concise bottom-line-up-front approach.
• Exceptional judgment and discretion when handling confidential executive-level information.
• Strong proficiency in Microsoft Office Suite, including PowerPoint, Excel, and Word, and executive-level presentation development.
• Working fluency with enterprise AI tools, such as Claude, for research, drafting, and synthesis, applied with sound judgment and executive-level discretion.

Nice To Haves

• Experience in executive support, consulting, strategy, or operations.
• Exposure to Board governance processes.
• Experience in insurance, financial services, or professional services.

Responsibilities

• Partner with the CEO's Office, including the Senior Executive Assistant and Chief of Staff, to prepare for Board and large-scale executive meetings, including agenda development, materials production, in-person setup, and logistics.
• Track meeting agendas, action items, and minutes, ensuring accountability and follow-through across stakeholders.
• Respond flexibly to changing business priorities, including off-hour events and time-sensitive matters requiring immediate attention or support.
• Support active enterprise transformation workstreams in coordination with the Business Transformation portfolio, including logistics and tracking across concurrent initiatives.
• Prepare executive briefing materials, pre-reads, and summaries for executive-level meetings by consolidating presentations, metrics, and strategic insights.
• Contribute to firm-level lessons-learned reviews and help communicate insights to relevant stakeholders.
• Coordinate touchpoints between the Business Transformation team and the Office of the CEO on shared initiatives.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level