Chief of Staff to Founder/CEO- Miami, FL

The Calendar Group
Miami, FL

Our client is seeking a strategic Chief of Staff to serve as a true right-hand to a Founder/CEO within a fast-growing ultra-luxury real estate investment firm. This role operates as a high-level partner driving execution, managing key relationships, and owning initiatives across deals and operations.

The Chief of Staff will act as an extension of the Founder, bringing judgment, context, and ownership across all priorities. The ideal candidate thrives in high-pressure environments, combines strategic thinking with hands-on execution, and operates with strong initiative and ownership.

Key Responsibilities

  • Act as a strategic partner to the Founder.
  • Support deal flow across development, brokerage, and capital raising
  • Prepare materials, including desks, memos, and presentations.
  • Interface with directly with brokers, attorneys, investors, and partners
  • Manage vendors and external stakeholders
  • Drive key initiatives and ensure follow-through
  • Prepare for and participate in meetings.
  • Build structure, systems, and operational processes
  • Anticipate needs, identify gaps, and proactively solve problems across both business and personal priorities.

Qualifications

  • 5+ years supporting a founder, executive, or UHNW principal in a high-performance environment.
  • Background in real estate, finance, private equity, or or investments preferred
  • Strategic thinker with strong execution skills
  • Excellent communication skills with the ability to interact confidentially with high-level stakeholders.
  • Tech-savvy (CRM systems, AI tools)
  • Spanish preferred
  • Must be authorized to work in the U.S.
  • Must pass a background check and provide verifiable references

Posted 2026-04-06

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