Office Administrator and Executive Assistant

Company Overview

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.

Position Overview

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.

Responsibilities

Executive Support

• 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
  
  

Office Administration

• 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, ID activation, 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
  
  

Event Planning

• 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
  
  

Legal & Closing Support

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
  
  

Requirements

• 3 years of experience in an administrative, executive assistant, or office management role, preferably in financial services or a professional services environment
• Bachelor’s degree preferred
• 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 with technology and willingness to learn firm-specific software
• Experience with event planning or coordination is a plus
• Familiarity with legal document handling or financial industry operations is a plus
• A proactive, solutions-oriented attitude with a genuine commitment to supporting the team
  
  

Compensation & Benefits

Obra Real Estate offers a competitive base salary of $75,000–$100,000 commensurate with experience, complemented by a comprehensive benefits package. This is a full-time, on-site position based in our Chicago office.

The firm also offers robust Benefits offerings which include Comprehensive Medical/Rx, Dental and Vision plans; 401(k) program with company match; Flexible Savings Accounts (FSA); Healthcare Savings Accounts (HSA) with company contribution; Basic and Voluntary Life Insurance; Long-Term Disability (LTD) and Short-Term Disability (STD) insurance; and Commuter Benefits plan for parking and transit. In addition all employees of Obra are provided with a daily lunch stipend.