Chief of Staff

Chesapeake Search Partners; Crofton (MD); On-site; USD 120,000 - 180,000; Full time

Job summary

Chesapeake Search Partners is partnering with a growing real estate organization to identify a Chief of Staff reporting directly to the Chief Financial Officer.

This highly visible role sits at the intersection of executive partnership, business operations, and project management, serving as an extension of the CFO to keep priorities moving across Accounting, Financial Reporting, HR, Property Management, Legal, and Asset Management.

Qualifications

• 5+ years of executive partnership or chief-of-staff experience.
• Experience with AI tools to improve processes and reporting.
• Strong presentation and reporting skills for executive-level audiences.

Responsibilities

• Serve as an extension of the CFO, managing priorities and preparing for key meetings.
• Lead cross-functional project tracking and monitor milestones across departments.
• Develop executive dashboards and visual reporting for visibility into priorities and progress.
• Attend key meetings with or on behalf of the CFO and drive follow-through with department leaders.
• Build and maintain project plans, schedules, and Gantt charts for multiple workstreams.
• Support process improvement and SOP development, including AI-enabled workflows.

Skills

Project management

Executive communication

Cross-functional collaboration

Tools

Monday.com

Job description

Chesapeake Search Partners is partnering with a growing real estate organization to identify a Chief of Staff reporting directly to the Chief Financial Officer. This highly visible role sits at the intersection of executive partnership, business operations, and project management, serving as an extension of the CFO to keep priorities moving across Accounting, Financial Reporting, HR, Property Management, Legal, and Asset Management. The ideal candidate is highly organized, proactive, and comfortable driving accountability across multiple senior-level stakeholders and initiatives.

Key Responsibilities:

• Serve as an extension of the CFO, managing priorities, preparing for key meetings, and helping drive execution across competing business needs.
• Lead cross-functional project tracking across multiple departments, identifying bottlenecks, monitoring milestones, and ensuring initiatives remain on schedule.
• Develop executive-level dashboards, roadmaps, presentations, and visual reporting that provide clear visibility into priorities, progress, and deliverables.
• Attend key meetings with or on behalf of the CFO, document decisions and action items, and drive follow-through and accountability across department leaders.
• Build and maintain project plans, schedules, timelines, and Gantt charts to manage multiple concurrent workstreams.
• Support process improvement, SOP development, AI-enabled workflows, and special projects that strengthen organizational effectiveness and executive decision-making.

Qualifications:

• 5+ years of experience in executive business partnership, Chief of Staff, business operations, or project management, ideally supporting C-suite or senior executives.
• Demonstrated project management experience with the ability to manage multiple complex initiatives, deadlines, and stakeholders simultaneously.
• Advanced proficiency with Monday.com, including project boards, Gantt views, and executive dashboards.
• Strong PowerPoint and visual communication skills with the ability to translate complex information into clear executive-level reporting.
• Experience leveraging AI tools to improve process documentation, drafting, workflows, and operational efficiency.
• Confident, proactive communication style with strong judgment, discretion, and the ability to drive accountability among senior leaders.