Executive Assistant & Transaction Coordinator to CEO

Wedgewood Investment Group; Chicago (IL); On-site; USD 60,000 - 90,000; Full time

Job summary

Wedgewood Investment Group is seeking a highly organized executive assistant to support the Owner and CEO. The role combines executive support with transaction coordination, sales support, and personal assistance in a dynamic CRE and equipment financing environment.

Responsibilities include calendar management, document drafting, deal tracking, and coordination with attorneys, lenders, investors, and clients. Strong IT skills and discreet, proactive work style are required.

Qualifications

• Highly organized, detail-oriented, dependable and discreet.
• Excellent command of Microsoft Office suite with proofreading and formatting skills.
• Comfortable learning and using AI tools and video-conferencing platforms.
• Ability to manage changing priorities and work independently.

Responsibilities

• Manage Owner/CEO calendars, emails, calls, travel, and meeting logistics.
• Draft and proofread sales proposals, reports, and transaction documents.
• Track deals, deadlines, and follow-ups with attorneys, lenders, investors, and clients.
• Support CRE and equipment leasing/financing opportunities with research and reporting.
• Maintain organized records, databases, and confidential documents.
• Prepare agendas, take notes, and manage action-items and follow-ups.
• Provide personal assistance and run local errands as needed.
• Handle general office tasks, vendor coordination, and IT coordination as needed.
• Assist with HR tasks, onboarding/offboarding, and employee questions.

Skills

Organizational skills

Communication

Problem-solving

Adaptability

Tools

Outlook

Word

Excel

PowerPoint

Teams

Zoom

Job description

Wedgewood Investment Group is seeking a highly organized executive assistant to support the Owner and CEO. The role combines executive support with transaction coordination, sales support, and personal assistance in a dynamic CRE and equipment financing environment.

Responsibilities include calendar management, document drafting, deal tracking, and coordination with attorneys, lenders, investors, and clients. Strong IT skills and discreet, proactive work style are required.