Executive Assistant to CEO

Overview

Holladay Ventures is seeking a high-performing, technology-forward Executive Assistant (EA) to the CEO, Evan Holladay. This is not a traditional administrative role. The EA will serve as a trusted partner who increases the CEO’s capacity, focus, and effectiveness by anticipating needs, creating operational leverage, and bringing order to complexity. The ideal candidate thrives in a dynamic, entrepreneurial environment and sees themselves as a strategic operator, not just a support function.

Holladay Ventures is a nationally award-winning real estate development company that specializes in developing impact-driven affordable housing solutions that are intentionally designed and make a positive difference in the lives of residents and the environment.

• Strategic & Executive Support
  • Serve as a trusted thought partner and “Force Multiplier” to the CEO, proactively identifying inefficiencies, risks, and opportunities.
  • Own and manage a complex calendar with intention—prioritizing high-value work and protecting focus.
  • Act as an assertive and thoughtful gatekeeper for meetings, requests, and interruptions.
  • Prepare agendas, capture meeting notes, and ensure consistent follow-up on action items.
  • Draft, edit, and manage correspondence on behalf of the CEO with investors, partners, and senior leaders.
  • Manage by clarifying priorities and helping the CEO stay aligned with top objectives.
  • Sit in meetings or represent CEO in meetings as needed.
• Project & Operations Management
  • Lead special projects from concept to completion, coordinating across internal and external stakeholders.
  • Design, document, and improve workflows that increase efficiency and reduce friction.
  • Oversee office and administrative operations, including vendor coordination and digital asset organization.
  • Assist Integrator as needed.
• Technology, Systems & Leverage
  • Own and continuously improve the CEO’s productivity systems (calendar, task management, documentation, and information flow).
  • Identify and implement tools, automation, and AI solutions that eliminate low-value work and increase leverage.
  • Confidently evaluate, adopt, and iterate on platforms such as Microsoft 365, and project management tools (Smartsheet, Click Up, Pipedrive, etc.), and knowledge management systems.
  • Troubleshoot technology issues independently and recommend smarter ways of working.
• Personal Support
  • Provide limited personal support for the CEO, including personal travel coordination, scheduling, household logistics, and gifting.
  • Occasionally travel with the CEO for conferences or events.
  • Handle all personal matters with discretion, professionalism, and clear boundaries.
  • Be available as needed for after hours or weekend events or tasks/work.

• 3+ years of experience as an Executive Assistant supporting a CEO, founder, or senior executive (real estate or entrepreneurial environment preferred).
• Proven ability to manage complexity, shifting priorities, and high-stakes communication.
• Demonstrated comfort managing up and operating with autonomy.
• Highly tech-savvy with a strong interest in systems, automation, and continuous improvement.
• Exceptional written and verbal communication skills.
• Extremely organized, detail-oriented, and reliable.
• High emotional intelligence, discretion, and integrity.
• Comfortable blending professional and limited personal support.
• Physically able to manage light office needs (ability to lift up to 20 lbs).

• Proactive:
  Anticipates needs and takes initiative without being asked.
• Committed:
  Follows through with excellence and consistency.
• Strategic & Tactical:
  Thinks ahead while executing flawlessly.
• Integrity:
  Maintains confidentiality and ethical standards at all times.
• Forward-Thinking:
  Embraces change and continuously seeks better ways to work.
• Flexible & Adaptable:
  Thrives in a fast-moving, evolving environment.
• Emotionally Intelligent & Positive:
  Brings professionalism, resilience, and calm under pressure.

• Sees themselves as a strategic partner, not “just an assistant.”
• Enjoys creating order out of chaos.
• Comfortable holding high standards and managing up.
• Balances urgency with thoughtful execution.
• Takes pride in being the leverage behind the leader.