Controller

Chesapeake Search Partners; Sterling (VA); On-site; USD 150,000 - 230,000; Full time

Job summary

Chesapeake Search Partners seeks a strategic financial leader to partner with ownership, overseeing multiple operating companies and real estate holdings. This role is ideal for a hands-on operator who can act as a trusted advisor and long-term business partner.

You will supervise accounting, treasury, and financial operations, lead cash flow forecasting, and manage banking relationships across entities, while maintaining discretion and integrity at the highest level.

Qualifications

• Active CPA with 10+ years of senior financial leadership experience.
• Experience in privately held and/or family-owned businesses.
• Background in commercial real estate, construction, development, or distribution.
• Experience managing multiple entities and investment structures.
• Strong banking, treasury, lending, and cash flow management expertise.

Responsibilities

• Oversee accounting, treasury, and financial operations across entities.
• Lead financial reporting and consolidation for multiple entities.
• Direct cash flow forecasting and capital planning.

Skills

Active CPA

Senior leadership

Strategic planning

Education

CPA certification

Job description

Chesapeake Search Partners is seeking a strategic financial leader to partner directly with ownership in overseeing multiple operating companies and real estate holdings. This is not a traditional Controller role as this is perfect for a hands on financial operator who can serve as a trusted advisor and long term business partner. This opportunity is ideal for a Controller or senior finance executive seeking a long term leadership role with direct exposure to ownership and meaningful influence on business strategy.

Responsibilities

• Oversee all accounting, treasury, and financial operations
• Manage financial reporting across multiple entities
• Lead cash flow forecasting and capital planning
• Manage banking relationships and lending structures
• Oversee lease portfolio financial performance
• Conduct investment analysis and entity management
• Partner directly with ownership on strategic planning and decision-making
• Coordinate with external CPA firms, legal counsel, and advisors
• Maintain strict confidentiality regarding all financial and business matters

Requirements

• Active CPA required
• 10+ years of senior financial leadership experience
• Experience within privately held and/or family-owned businesses
• Background in commercial real estate, construction, development, and/or distribution
• Experience managing multiple entities and investment structures
• Strong banking, treasury, lending, and cash flow management expertise
• Understanding of tax strategy and entity structuring
• Proven ability to work directly with ownership and executive leadership
• Strong operational, strategic, and decision-making capabilities
• High level of discretion, professionalism, and integrity