Title: Associate Chief of Staff - Apprenticeship Location: Tampa, FL (in-office, 5 days per week) This role offers direct exposure to executive leadership, enterprise strategy, and operational execution at the highest levels of the firm. Designed as an apprenticeship gateway for future business leaders within The Baldwin Group, it places you alongside the CEO, Chief of Staff, Executive Leadership Team, and Operating Segment Presidents, where you will help drive key business processes and ensure seamless coordination across functions. You will gain a front-row seat to business transformation and operations, learning how to navigate leadership dynamics, executive decision-making, and cross-functional collaboration. PRIMARY RESPONSIBILITIES Executive Meeting Support — Office of the CEO · Partner with the CEO's Office (Senior Executive Assistant, Chief of Staff) to prepare for Board and large-scale executive meetings, from agenda development and materials production to in-person setup and logistics, ensuring accuracy, completeness, and seamless execution · Track agendas, action items, and meeting minutes, ensuring accountability and follow-through across stakeholders · Maintain flexibility to respond to evolving business priorities, which may include off-hour events and time-sensitive matters requiring immediate attention or support Business Transformation and Strategic Initiative Support — Office of the Chief of Staff · 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, consolidating presentations, metrics, and strategic insights · Contribute to firm-level lessons-learned reviews and help ensure insights are communicated to relevant stakeholders · Coordinate touchpoints between the Business Transformation team and the Office of the CEO on shared initiatives EDUCATION AND EXPERIENCE This role is ideal for a recent master's graduate, early-career professional (2 - 4 years out of undergrad), or Junior Military Leader with exceptional communication, problem-solving, and organizational skills, who is eager to accelerate a path to leadership. KNOWLEDGE, SKILLS, AND ABILITIES REQUIRED · High-potential early-career professional with a strategic mindset and strong analytical skills · Proactive problem-solver who thrives in fast-paced, high-visibility environments · Exceptional attention to detail, ensuring accuracy and alignment in all deliverables · Comfortable managing competing priorities across multiple stakeholders, moving fluidly between operational and strategic work · Excellent written and verbal communication skills, with 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 handling executive-level confidential information TECHNICAL, COMPUTER, AND SYSTEM SKILLS Strong proficiency in Microsoft Office Suite (PowerPoint, Excel, Word) and executive-level presentation development Working fluency with enterprise AI tools (e.g., Claude) to accelerate research, drafting, and synthesis, applied with sound judgment and executive-level discretion NICE TO HAVE · Experience in executive support, consulting, strategy, or operations · Exposure to Board governance processes · Experience in insurance, financial services, or professional services This description indicates the general nature and level of work performed by colleagues in this role. It is not intended to be a comprehensive inventory of all duties, responsibilities, and qualifications. Duties may be assigned or modified as the firm's needs evolve. IMPORTANT NOTICE: This position description is intended to describe the level of work required of the person performing in the role and is not a contract. The essential responsibilities are outlined; other duties may be assigned as needs arise or as required to support the organization. All requirements may be subject to reasonable accommodation to applicants and colleagues who need them for medical or religious reasons. Click here for some insight into our culture! The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume. The Baldwin Group is a cohesive group of experts in business insurance, employee benefits, retirement planning, and all areas of private and personal insurance. Since 2011, we’ve evolved from a local business into a national firm with a vast network of specializations serving two million clients across the country. At The Baldwin Group, we provide solutions so our clients can pursue what’s possible for themselves, their families, and their businesses. Whether renting a first apartment, opening a small business or taking a company public, we offer solutions to support clients at every step of their journey giving them peace of mind to pursue their purpose, passion, and dreams. We Protect the Possible. The Baldwin Group is an equal employment opportunity firm and strives to comply with all laws prohibiting discrimination based on race, color, religion, age, sex (including sexual orientation and gender identity), national origin or ancestry, disability, military status, marital status, and any other category protected by federal, state, or local laws. All such discrimination is unlawful, and all persons involved in the operations of the firm are prohibited from engaging in this conduct.

Associate Chief of Staff - Apprenticeship - Onsite Tampa.

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