Operational Chief of Staff

Keller Executive Search; Crofton (KY); Hybrid; USD 110,000 - 150,000; Full time

Benefits offered by this job

Competitive benefits

Job summary

Keller Executive Search is seeking an Operational Chief of Staff to sit with the CFO and drive execution across the company. The role focuses on turning strategic priorities into tracked work, partnering with senior leaders, and managing cross-functional initiatives.

The position emphasizes structure, accountability, and proactive leadership, with hybrid work and periodic board-level involvement. Strong Monday.com and Excel skills are essential.

Qualifications

• 5 to 7+ years of executive partnership, chief of staff, operations, or project management experience.
• Ability to manage multiple active workstreams and hold leaders accountable.
• Proficient in Monday.com boards, Gantt views, and dashboards for reporting.
• Advanced Excel skills and strong visual reporting capabilities.
• Direct, pragmatic communication style with discretion and judgment.
• Self-directed, proactive problem solver comfortable with senior leadership.

Responsibilities

• Serve as strategic partner and operational extension of the CFO, prioritizing work and preparing meetings.
• Act as an operational proxy in cross-functional check-ins; surface bottlenecks and drive progress.
• Build and maintain executive dashboards, roadmaps, and milestone updates.
• Track projects from kickoff to completion with timelines and status reporting.
• Attend key operational meetings, capture decisions, and drive follow-through.
• Document and improve internal processes and SOPs, leveraging AI tools.
• Lead special projects and executive problem-solving as needed.

Skills

Executive partnership

Chief of staff

Project management

Cross-functional collaboration

Tools

Monday.com

Excel

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.

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.

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

Use of Artificial Intelligence in Recruitment

Keller Executive Search and our clients may use artificial intelligence (AI) tools to assist in the recruitment and candidate evaluation process. These tools are used exclusively to support human decision-making by helping to review and assess candidate qualifications and materials. AI is never used to automatically reject, disqualify, or make final hiring decisions about candidates. All AI-assisted evaluations are reviewed by experienced recruitment professionals, and all hiring decisions are made by qualified human recruiters. Our use of AI is designed to enhance fairness, consistency, and efficiency while maintaining our commitment to equal employment opportunity and non-discrimination principles.

Genetic Information

In accordance with federal and state laws, both Keller Executive Search and our clients do not discriminate based on genetic information. We do not request or require genetic information from applicants or employees, except as permitted by law.

Local Laws

Both Keller Executive Search and our clients comply with all applicable local laws and ordinances regarding employment practices in the areas where we operate.

Note

This job posting may be for a position with Keller Executive Search or one of our clients. The specific employer will be identified during the application and interview process. Employment laws and requirements may vary depending on the employer and location.

Equal Employment Opportunity and Non-Discrimination Policy

Both Keller Executive Search and our clients are Equal Opportunity Employers. For all positions, whether with Keller Executive Search or our clients, qualified applicants will receive consideration for employment without regard to race, skin color, religion, sex, sexual orientation, gender identity, gender expression, national origin, age, protected veteran status, disability, genetic information, or any other legally protected status.

Equal Employment Opportunity Statement

Both Keller Executive Search and our clients are Equal Opportunity Employers. For all positions, whether with Keller Executive Search or our clients, qualified applicants will receive consideration for employment without regard to race, skin color, religion, sex, sexual orientation, gender identity, gender expression, national origin, age, protected veteran status, disability, genetic information, or any other legally protected status.

Commitment to Diversity

Keller Executive Search and its clients are committed to fostering a diverse and inclusive work environment where all individuals are valued and respected.

Reasonable Accommodations

Both Keller Executive Search and our clients are committed to providing reasonable accommodations to individuals with disabilities and pregnant individuals. We engage in an interactive process to determine effective, reasonable accommodations.

Compensation Information

For client positions, compensation information is available in the job post. If not provided, it will be shared during the interview process in accordance with applicable laws. When required by law, salary ranges will be included in job postings. Actual salary may depend on skills, experience, and comparison to current employees in similar roles. Salary ranges may vary based on role and location.

Compliance with Laws

Both Keller Executive Search and our clients comply with federal, state, and local laws governing nondiscrimination in employment. This policy applies to all employment terms and conditions, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Workplace Harassment

Both Keller Executive Search and our clients expressly prohibit any form of workplace harassment based on race, skin color, religion, gender, sexual orientation or expression, national origin, age, genetic information, disability or veteran status.

E-Verify Participation

Keller Executive Search and/or our clients may participate in E-Verify. Information about E-Verify participation will be provided during the application process where applicable.

Privacy and Pay Equity

• California Residents: For more information about the categories of personal information we collect for recruiting and employment purposes, please review our Privacy Policy at www.kellerexecutivesearch.com.
• Colorado, Nevada, New York City, California, and Washington Residents: Compensation information is available in the job post or will be provided during the interview process if not initially available.
• Both Keller Executive Search and our clients are committed to pay equity and conduct periodic pay equity analyses in accordance with applicable laws.

State-Specific Information

• Rhode Island: We do not request or require salary history from applicants.
• Connecticut: We provide wage range information upon request or before discussing compensation.
• New Jersey: We do not inquire about salary history unless voluntarily disclosed.

Veteran Status

Both Keller Executive Search and our clients provide equal employment opportunities to veterans and comply with applicable state laws regarding veteran preference in employment. If you are a veteran, please inform us during the application process.