Executive Assistant/Operations Manager

Dayton Street Partners LLC; Chicago (IL); On-site; USD 65,000 - 85,000; Full time

Job summary

Dayton Street Partners LLC in Chicago is seeking an Executive Assistant / Operations Manager to serve as the quarterback of our business operations. This role goes beyond calendar management and will be the right hand to the Principals, anticipating needs, coordinating key initiatives, and driving execution across the organization.

This role suits someone who thrives in a fast-paced environment, takes charge without constant direction, and wants a central role in scaling a growing real estate

Qualifications

• 3+ years in executive support, chief of staff, or operations.
• Self-starter with ownership and accountability.
• Exceptional organization, communication, and problem-solving skills.
• Ability to manage multiple priorities calmly.
• Discretion and professionalism with confidential information.
• Proficient in Microsoft Office and common design/website tools; property software a plus.

Responsibilities

• Serve as the primary point of contact between the Principals and internal and external stakeholders.
• Manage the Principals' calendars and prioritize meetings.
• Prepare agendas, take concise notes, and drive follow-through on action items.
• Keep the Principals briefed with context, data, and updates to enable quick decisions.
• Own internal projects, maintain deadlines, and align stakeholders.
• Coordinate across acquisitions, asset management, and vendors; schedule tours and meetings.

Skills

Executive support

Organization

Communication

Problem-solving

Multitasking

Discretion

Tools

Microsoft Office

Outlook

Teams

Excel

PowerPoint

Word

Adobe

WordPress

Rent Manager

Job description

Location: Chicago (River North), onsite Monday–Friday

Reports To: Principals

Type: Full-Time

About the Role

We're looking for a highly organized, proactive Executive Assistant / Operations Manager to serve as the quarterback of our business operations. This role goes well beyond calendar management. You'll be the right hand to the Principals: anticipating needs, coordinating key initiatives, and driving execution across the organization.

This role suits someone who thrives in a fast-paced environment, takes charge without constant direction, and wants a central role in scaling a growing real estate business.

Key Responsibilities

Executive Support

• Serve as the primary point of contact between the Principals and internal and external stakeholders
• Manage the Principals' calendars and prioritize meetings
• Prepare agendas, take concise notes, and drive follow-through on action items
• Keep the Principals briefed with the right context, data, and updates to make quick decisions
• Own internal projects, keeping deadlines on track and stakeholders aligned
• Identify workflow gaps and recommend improvements

Communications & Brand

• Draft correspondence, presentations, and reports
• Maintain the company website, including content updates and listings
• Manage the company's LinkedIn presence with a consistent brand voice
• Track deal flow and key timelines for acquisitions, leases, and dispositions
• Support due diligence by gathering and organizing property documents, contracts, and vendor materials
• Coordinate across acquisitions, asset management, the Principals, and third parties
• Schedule property tours, inspections, and meetings
• Maintain internal databases, project files, and document storage
• Open property bank accounts for new acquisitions and refinances
• Prepare service contracts and engage vendors
• Respond to tenant requests
• Deposit rent checks and reconcile credit card statements
• Handle travel planning and day-to-day office management
• Coordinate with third party IT provider

Qualifications

• 3+ years in executive support, chief of staff, or operations
• Self-starter with a strong sense of ownership and accountability
• Exceptional organization, communication, and problem-solving skills
• Able to manage multiple priorities calmly
• Discretion and professionalism with confidential information
• Proficient in Microsoft Office (Outlook, Teams, Excel, PowerPoint, Word), Adobe, and WordPress; Rent Manager or similar property management software a plus
• Experience with LLC formation and related filings
• Illinois notary, or willing to become one within 120 days of start