Office Administrator and Executive Assistant

Obra Capital, Inc.•Chicago, IL

13d•$75,000 - $100,000•Onsite

About The Position

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.

Requirements

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 with technology and willingness to learn firm-specific software
A proactive, solutions-oriented attitude with a genuine commitment to supporting the team

Nice To Haves

Bachelor’s degree preferred
Experience with event planning or coordination is a plus
Familiarity with legal document handling or financial industry operations is a plus

Responsibilities

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, 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
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
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