Office Administrator and Executive Assistant

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Chicago, IL, US

Today Requisition

$65,000.00 to $95,000.00 annually

Obra Real Estate, LLC ("ORE") is a nationwide, direct commercial real estate lender specializing in bridge and transitional financing. A subsidiary of Obra Capital— a specialized alternative asset management firm with expertise across structured credit, asset-based finance, insurance special situations, and private lending— ORE combines institutional‑quality underwriting with the speed and flexibility that sponsors and borrowers demand. ORE differentiates itself through disciplined credit underwriting, in‑house servicing, and a commitment to relationship‑driven execution.

Obra Real Estate is seeking a highly organized and proactive Office Administrator & Executive Assistant to join our Chicago team. This is a dual‑function role that sits at the center of our office operations and provides direct executive support to senior leadership. The ideal candidate is a self‑starter who thrives in a fast‑paced, professional environment, exercises sound judgment and discretion, and takes genuine pride in keeping things running smoothly.

This position is full‑time and on‑site in our Chicago office.

• Provide high‑level administrative support to three senior leaders, including calendar management, scheduling, and prioritization of competing demands
• Coordinate complex domestic and international travel arrangements, including flights, hotels, ground transportation, and itineraries
• Prepare correspondence, presentations, and briefing materials on behalf of leadership
• Screen and manage incoming communications; triage email and phone inquiries with discretion
• Anticipate needs, proactively manage schedules, and help leadership stay ahead of deadlines
• Handle sensitive and confidential information with the utmost discretion and professionalism
• Assist with expense reporting and reconciliation

• Manage day‑to‑day office operations, ensuring a professional, welcoming, and well‑functioning work environment
• Oversee supply ordering and inventory management; maintain appropriate stock levels and manage vendor relationships
• Coordinate employee onboarding logistics, including workstation setup, security access, , and new hire orientation support
• Serve as primary point of contact with building management, IT vendors, and facilities for maintenance, repairs, and technology coordination
• Manage mail, shipping, receiving, and courier services

• Plan and execute internal events, including team gatherings and holiday parties, from concept through execution
• Coordinate external ORE‑sponsored events such as Mortgage Madness and other firm‑hosted functions, managing logistics, vendors, invitations, and on‑site execution
• Track event budgets and manage vendor contracts and payments

In close coordination with the legal team, this role provides operational support for loan closings and document management:

• Deliver hard copies of legal documents to the custodian as required
• Serve as the primary point of contact for receipt of incoming loan document deliveries
• Coordinate note exchanges and assist with updating and maintaining hard copy records
• Facilitate the arrangement and collection of signatures across internal and external parties
• Prepare and organize signature page packets for closing transactions

• 3+ years of experience in an administrative, executive assistant, or office management role, preferably in financial services or a professional services environment
• Exceptional organizational and time management skills with strong attention to detail
• Demonstrated ability to manage multiple priorities and work effectively under pressure
• Strong written and verbal communication skills; professional and polished demeanor
• High level of discretion and sound judgment when handling confidential matters
• Proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint); comfort…