Operational Chief of Staff

Job Description

Job Description

Our client is a well-established, growing real estate investment and property management organization in the Crofton, MD area. As the business scales and matures its operating model, they are seeking an Operational Chief of Staff to sit alongside the Chief Financial Officer and help drive execution across the company.

This is a high-visibility, high-trust position for someone who thrives on structure, accountability, and turning strategic priorities into tracked, completed work. It is built for a proactive operator who can partner directly with a C-suite executive, manage complex cross-functional initiatives, and hold senior leaders accountable without hesitation.

What You Will Do

• Serve as a strategic partner and operational extension of the CFO, managing priorities, meeting preparation, and competing demands to maximize executive leverage.
• Act as an operational proxy in cross-functional check-ins, running down project updates, surfacing bottlenecks, and keeping multi-departmental initiatives on schedule across functions such as Accounting, Financial Reporting, HR, Property Management, Legal, and Asset Management.
• Build and maintain executive-level visual dashboards, roadmaps, and companywide milestone updates using various technologies and tech tools.
• Track cross-functional projects from kickoff to completion, including timelines, Gantt views, and status reporting.
• Attend key operational meetings with or on behalf of the CFO, capture decisions, document action items, and drive follow-through across department heads.
• Support the documentation and continuous improvement of internal processes and SOPs, leveraging AI tools to streamline workflow documentation.
• Lead special projects and executive problem-solving as new business needs arise.

Working Conditions:

• Hybrid schedule: 3 days on-site per week, with flexibility on the remaining days.
• Occasional travel expected, approximately 5 to 10%, including periodic Board meetings.

Requirements

Required:

• 5 to 7+ years of experience in executive business partnership, chief of staff, business operations, or project management, ideally supporting a C-suite or senior executive.
• Demonstrated project management skill, including building project plans, milestone tracking, and running multiple active workstreams at once.
• Advanced proficiency with Monday.com (boards, Gantt views, dashboards) and strong presentation or visual reporting skills.
• Advanced Excel skills.
• A confident, direct, and pragmatic communication style, with the poise to hold senior leaders and department heads accountable to commitments.
• High discretion, sound judgment, and experience handling confidential executive and financial information.
• A self-directed, proactive style that anticipates needs rather than waiting for direction.

Preferred:

• Background in real estate or property management, including familiarity with acquisitions, dispositions, investor relations, or multi-site operations.

Benefits

• Base range $110k to $150k (commensurate with experience)
• Competitive benefits and incentive structure

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