Executive Assistant

Wedgewood Investment Group, LLC; 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

We are seeking a highly organized, dependable, and adaptable individual to provide direct executive, administrative, sales, and personal support to the Owner and CEO of a commercial real estate investment and Owner of an equipment leasing/financing firm.

ABOUT THE POSITION

This is a hands-on position for someone who can become a trusted right-hand person to an active and entrepreneurial business owner. The role combines executive assistant responsibilities with transaction coordination, sales support, personal assistance, business errands, and general problem-solving.

The Owner and CEO is regularly involved in numerous transactions, meetings, properties, financing opportunities, and business activities at the same time. Priorities can change throughout the day, so the successful candidate must be responsive, resourceful, flexible, and comfortable taking ownership of a wide variety of responsibilities.

PRIMARY RESPONSIBILITIES

• Manage calendars, email, calls, meeting preparation, reminders, correspondence, travel, and event logistics for the Owner and CEO.
• Draft, type, format, and carefully proofread sales proposals, reports, transaction documents, financial materials, letters, spreadsheets, and presentations.
• Track deals, signatures, deadlines, commitments, and follow-up items while coordinating with attorneys, lenders, investors, clients, vendors, and business partners.
• Support commercial real estate and equipment leasing or financing opportunities through research, credit-package preparation, sales reporting, contact management, and transaction coordination.
• Maintain organized digital and physical records, contact databases, shared-drive files, confidential documents, and materials used on computers and mobile devices.
• Prepare agendas and recurring reports, attend meetings when requested, take accurate notes, and maintain action-item and follow-up lists.
• Provide personal assistance, including appointments, reservations, travel, purchases, household or service-vendor coordination, and local errands.
• Perform general office administrative work, including managing office-supply inventory, shipping and deliveries, document organization, vendor coordination, office maintenance requests, and confidential shredding.
• Support employee recruiting, onboarding, offboarding, HR documentation, employee questions, directory updates, and basic IT coordination.
• Assist with receipts, expense documentation, invoices, statements, and other confidential financial or administrative records.
• Provide basic technology support involving Outlook, Teams, Zoom, Word, Excel, PowerPoint, iPads, phones, computers, and artificial intelligence tools.
• Anticipate needs, exercise sound judgment, maintain absolute confidentiality, and take ownership of assignments without constant supervision.

IDEAL CANDIDATE

• Highly organized, detail-oriented, dependable, professional, discreet, and responsive.
• Excellent command of Microsoft Outlook, Word, Excel, and PowerPoint, with strong proofreading and document-formatting skills.
• Comfortable learning and using artificial intelligence, mobile devices, video-conferencing platforms, and other productivity tools.
• Able to manage changing priorities, communicate professionally, and follow through independently in a varied work environment.
• Comfortable handling both business and personal responsibilities and completing local errands.
• Previous executive assistant, administrative, commercial real estate, legal, finance, equipment leasing, sales support, or office-management experience is preferred.
• Willingness to obtain CPR/AED and notary certifications at company expense, if not already certified.
• Reliable transportation and the ability to complete local business and personal errands are required.

POSITION DETAILS

Employment - Full-time