Executive Assistant to Chief Financial Officer

Company Description

Gatehouse Design and Developments specializes in designing and building high-quality homes with a focus on craftsmanship and attention to detail. Dedicated to enhancing how people live, the team prioritizes thoughtful planning and livability in every project, ensuring a seamless homeowner experience. By collaborating with highly skilled professionals, Gatehouse upholds a strong commitment to quality and precision. Every project reflects pride in workmanship and a passion for creating homes that embody character and meaning. The team's values are grounded in respect, skill, and a mission to elevate industry standards.

About the Role

We're looking for a highly capable, innovative Executive Assistant
who will serve as a true partner to the CFO—not just maintain systems, but
add value, improve processes, and think strategically
about how finance and operations support our growth.

This role blends high-level executive support with
hands-on finance operations (AR/AP, QuickBooks Online, project tracking)
plus light legal/transactional coordination across multiple entities and joint ventures. You'll work in-office and be deeply embedded in the day‑to‑day engine of the business.

This is ideal for someone who:

• Understands the
  big picture
  behind the numbers and structures.
• Enjoys
  building and improving systems
  , not just following them.
• Likes working with
  multiple entities, org charts, and deal structures
  in a fast-moving real estate environment.

Key Responsibilities

Executive Support to the CFO

• Manage the CFO's calendar, meetings, and priorities across
  multiple projects, entities, and partners
  .
• Organize and prepare materials for lender, investor, and internal finance meetings (agendas, financial summaries, supporting documents).
• Draft, edit, and organize emails and correspondence on behalf of the CFO, maintaining a professional tone with lenders, investors, attorneys, and partners.
• Anticipate information and support needs—proactively surface issues, deadlines, and opportunities for improvement.

Finance & Project Support

• Handle day-to-day finance tasks, including:
• End-to-end AR/AP management
  (5+ years' experience): vendor invoices, payment runs, aging reports, and reconciliations.
• Entering and maintaining
  clean books in QuickBooks Online
  (2+ years' hands-on experience required).
• Coordinating with external accountants/bookkeepers to ensure accuracy and completeness.
• Assist with monthly/quarterly reporting packages for projects and corporate entities.
• Track key financial dates and obligations: loan draws, interest payments, tax deadlines, lender and investor reporting.
• Maintain organized digital folders and filing systems for financial statements, loan documents, development budgets, and draw packages.
• Use
  advanced Excel skills
  (pivot tables, lookups, formulas) to build and maintain trackers, reconciliations, and reports.

Legal, Entity & Transactional Coordination (Asset Skill)

• Support coordination of transaction documents for acquisitions, financings, and dispositions (PSAs, loan agreements, easements, leases) in collaboration with outside counsel.
• Maintain and organize corporate/entity records: LLCs, operating agreements, resolutions, signature pages, etc.
• Assist with
  incorporation and entity setup
  across multiple organizations, including maintaining org charts and entity structures.
• Understand and help track
  different company setups
  , including
  joint venture agreements
  and partner structures (not providing legal advice, but understanding the mechanics and documentation).
• Track critical dates (closing dates, contingencies, option periods, renewal options, notice deadlines) and surface them to the CFO in advance.
• Review basic documents for completeness and consistency and coordinate revisions with attorneys, counterparties, and internal stakeholders.

Process, Systems, AI & Optimization

• Build and refine checklists, trackers, templates, and SOPs for:
• Closings and loan draw processes.
• Quarterly reporting and recurring finance tasks.
• Document management, approvals, and signature workflows.
• Leverage AI tools
  (e.g., ChatGPT/Copilot-type tools) to:
• Draft emails, summaries, and standardized documents.
• Help analyze data, detect inconsistencies, and improve reporting.
• Streamline repetitive tasks and improve overall productivity.
• Continuously look for ways to
  improve and modernize systems
  , reduce friction, and speed up information flow to and from the CFO.
• Monitor outstanding tasks and follow-ups, making sure projects and obligations move forward on schedule.

Cross-Functional & Stakeholder Coordination

• Coordinate with internal teams (development, construction, property management, accounting) to gather information needed by the CFO.
• Serve as a professional, responsive point of contact for lenders, investors, partners, and legal counsel seeking information from the CFO.
• Handle sensitive and confidential information with discretion and sound judgment.

Required Qualifications

• 5+ years
  of experience in a finance/operations support role such as Executive Assistant to a senior finance leader, Operations Coordinator, or similar.
• Minimum 5 years of hands-on AR/AP experience
  , including managing invoice workflows, payment runs, and reconciliations.
• Minimum 2 years of hands-on experience with QuickBooks Online
  (not just desktop) including multi-entity setups, classes, and project/department coding.
• 5+ years of Microsoft Office Suite experience
  with
  advanced skills in Excel and Word
  (complex formulas, pivot tables, formatting, mail merges, templates).
• Demonstrated
  experience working with multiple entities
  , org charts, and incorporation processes.
• Understanding of
  different company setups
  , including joint ventures and partnerships, and how they show up in documents and basic financials.
• High attention to detail, with a track record of
  low error rates
  in financial and legal/transactional documents.
• Comfort using and learning
  AI tools
  and technology platforms to improve workflows and productivity.
• Excellent written and verbal communication skills; able to communicate clearly and professionally with external stakeholders.

Preferred / Asset Experience

• Experience in
  real estate, construction, or development
  (strong plus).
• Banking and/or paralegal/legal assistant experience
  —especially in real estate, corporate, or transactional law—is a significant asset.
• Working knowledge of basic accounting and finance concepts beyond AR/AP (general ledger, project-based financials, budgets, soft vs. hard costs).
• Experience with other accounting or project management tools (e.g., Yardi, Procore, or similar) is a plus.
• Bachelor's degree in Business, Finance, Real Estate, or related field preferred (or equivalent experience).

Personal Traits & Working Style

We're looking for someone who:

• Brings a
  proactive, "value-add" mindset
  —anticipates needs and suggests improvements instead of waiting for direction.
• Understands the
  bigger picture
  of how finance, entities, and deals fit together—and enjoys learning more about it.
• Is extremely
  organized and detail-focused
  , comfortable managing many moving parts across multiple projects and entities.
• Enjoys
  structure, systems, and optimization
  —likes building better processes and keeping everything neat and trackable.
• Thrives in a
  fast-paced, deadline-driven environment
  typical of real estate closings, loan draws, and development milestones.
• Has a
  high sense of urgency and follow-through
  , keeping tasks moving until they're fully completed.
• Is comfortable working with both
  numbers and documents
  —spreadsheets, financial reports, contracts, and closing binders.
• Operates with
  discretion, integrity, and professionalism
  at all times.

Please email cover letter and resume to