Strategic Executive Assistant to CEO (In-Office)

DL3 Realty; Chicago (IL); On-site; USD 70,000 - 90,000; Full time

Benefits offered by this job

Medical, dental, and vision insurance

Paid time off and paid holidays

401(k) with company match

Job summary

DL3 Realty, a Chicago-based real estate investment and development firm, seeks an Executive Assistant to support the CEO and manage the office. The role is in-office in Chicago, requires flexibility for after-hours events, and offers growth opportunities within a fast-paced entrepreneurial environment.

You will handle calendars, meetings, travel, presentations, vendor relations, and basic accounting tasks, while maintaining discretion and professionalism when interacting with investors,

Qualifications

• Bachelor’s degree preferred in business, finance, real estate, communications, marketing, or a related field.
• 4-6 years of experience as an Executive Assistant or in a high-level administrative support role providing direct support to senior executives, business owners, or leadership teams.
• Active Notary Public commission preferred, or ability and willingness to obtain certification upon hire
• Experience with Canva and Adobe Creative Suite, including InDesign, is required
• Proficiency with Microsoft Office Suite, including PowerPoint, Word, Outlook, and Excel, is required
• Experience with CRM systems, Salesforce, or similar platforms is preferred
• Interest in or familiarity with real estate, finance, investing, or professional services environments is strongly preferred
• Demonstrated experience managing executive calendars, coordinating complex schedules and travel, preparing presentations and meeting materials, and supporting executive meetings or board engagements
• Strong organizational skills with the ability to manage multiple priorities, deadlines, and confidential information
• Exceptional written and verbal communication skills with a high level of professionalism

Responsibilities

• Manage and maintain the CEO’s calendar, including scheduling meetings, coordinating appointments, and prioritizing competing demands
• Prepare meeting agendas, materials, presentations, briefing documents, and other resources needed for CEO meetings, company board meetings, external board engagements, speaking opportunities, and business activities
• Support preparation for company board meetings and external board engagements, including coordinating agendas, materials, presentations, schedules, meeting logistics, and follow-up items
• Create and edit professional presentations, documents, and communications using tools such as Microsoft Office, Canva, Adobe Creative Suite, and InDesign
• Coordinate domestic travel arrangements, conference registrations, detailed itineraries, and meeting logistics
• Support planning and execution of industry, community, charitable, philanthropic, and business development events and commitments
• Manage communications and correspondence with investors, government officials, tenant prospects, C-level executives, vendors, board members, and other external stakeholders
• Prepare CEO and leadership team members for meetings by ensuring necessary information, materials, and logistics are organized in advance
• Coordinate executive meetings, including refreshments, meals, conference room preparation, and overall meeting experience
• Maintain executive contacts, business card records, CRM information, and relationship management systems
• Coordinate employee recognition initiatives, team-building activities, and internal events that support a positive and collaborative office culture.
• Assist with light accounting support, including budget tracking, expense reconciliation, and other financial coordination as needed
• Assist with special projects, research, and business initiatives as assigned by the CEO
• Represent the company professionally at meetings, events, and external engagements
• Anticipate CEO needs and proactively identify opportunities to improve organization, efficiency, and effectiveness

Skills

Calendar management

Executive support

Travel coordination

Microsoft Office

PowerPoint

Word

Outlook

Excel

Canva

Adobe InDesign

Salesforce

Education

Bachelor’s degree preferred

Tools

Canva

Adobe Creative Suite

InDesign

Salesforce

Microsoft Office Suite

Job description

DL3 Realty, a Chicago-based real estate investment and development firm, seeks an Executive Assistant to support the CEO and manage the office. The role is in-office in Chicago, requires flexibility for after-hours events, and offers growth opportunities within a fast-paced entrepreneurial environment.

You will handle calendars, meetings, travel, presentations, vendor relations, and basic accounting tasks, while maintaining discretion and professionalism when interacting with investors,