Executive Assistant

Job Title: Executive Assistant to the CEO

Reports To: CEO

Job Type: Full-Time, Remote

Experience Level:  Mid-Senior Level

Location: Remote

Executive Assistant to the CEO

Role Summary

As a Executive Assistant to the CEO, you will function as a strategic extension of the CEO: tracking every decision to completion, drafting and answering email on the CEO's behalf, keeping the systems that run the business current, and making sure nothing gets dropped. You'll also work with the broader team to support important projects and operational work on behalf of the CEO. We're looking for someone with real fluency in the real estate investment industry preferably syndications. Ideally, you should be able to draft to an investor or broker, jump on a collaboration call, and hold your own without additional support, always ready to conduct the research needed or reach out to the right person to give you the answer you need to just get the job done.

Key Responsibilities

Strategic Extension of the CEO

• Attend the CEO's investor, collaboration, partner, and team meetings; capture decisions and drive follow-up to completion without being asked.
• Answer questions in real time during meetings so the CEO can stay present and lean on you for information on the spot.
• Anticipate what the CEO needs before it's requested - surface priorities, flag risks, and manage the calendar and inbox with judgment, not just logistics.
• Prepare briefing materials and talking points ahead of investor, partner, and deal meetings.

Inbox & Communication

• Own the CEO's inbox: draft replies for quick approval, send on the CEO's behalf, and make sure nothing slips through unread or unanswered.
• Act as a second set of eyes so emails don't get missed or mis-routed - audit for dropped balls and catch them before they become problems.
• Acknowledge investor inquiries and hand them cleanly to the appropriate IR rep, reinforcing the handoff so the CEO can step back out of day-to-day investor relations.
• Draft on the CEO's behalf to investors, sponsors, brokers, and partners in a clear, credible voice.

Relationship & Deal Coordination

• Maintain the CEO's network map across investors, sponsors, brokers, and partners spanning all four portfolio companies.
• Proactively identify who should be connected to whom to move a capital raise, joint venture, or deal forward - and make those introductions.
• Nurture key relationships between transactions so they're warm and ready when the CEO needs them.
• Support deal-flow logistics: scheduling diligence calls, tracking documents, and coordinating with legal and finance counterparts.
• Keep templated legal instruments and key documents organized and findable (e.g., PPM, operating agreement, subscription agreement, addenda) so the CEO can get to them instantly.

Systems & Operations

• Keep ClickUp and HubSpot current - projects, owners, deadlines, and sales activity - so the CEO and Ben never have to chase status.
• Maintain a centralized CEO directory of the links, sheets, and documents the CEO reaches for most, so nothing turns into a fire drill.
• Track the CEO's priorities and brain-dumps, translate them into owned action items, and follow up with the relevant leaders for updates.

Cross-Portfolio Operations

• Coordinate priorities and communication across different departments
• Keep projects, tasks, and follow-ups organized; manage documents and correspondence in Google Workspace

Required Qualifications

• 5+ years supporting a founder, CEO, or executive in an EA, executive support, or operations coordination capacity.
• Working knowledge of real estate investing, syndications, and/or fund structures (LP/GP, capital calls, waterfalls) - enough to speak credibly with investors and brokers without translation.
• Excellent written and verbal communication; comfortable drafting and replying on the CEO's behalf.
• Demonstrated discretion and sound judgment handling confidential business and financial information.
• Proficiency with Google Workspace and task/project management tools (ClickUp preferred); comfortable in a CRM (HubSpot a plus).
• U.S.-based with availability aligned to Eastern time zone, including flexibility for occasional after-hours or weekend coverage when needed.

Preferred Qualifications

• Prior experience inside a real estate syndication, family office, or multi-entity founder-led business.
• Experience managing or directing other support staff.
• Hands-on experience using AI tools to streamline executive and operational workflows.