Executive Assistant to the CEO

Holladay Ventures • Nashville, TN

2d

About The Position

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 who specializes in developing impact-driven affordable housing solutions that are not only intentionally designed but also make a positive difference in the lives of residents and the environment.

Requirements

• 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).

Nice To Haves

• real estate or entrepreneurial environment preferred

Responsibilities

• 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
• 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
• 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, ClickUp, Pipedrive, etc.), and knowledge management systems.
• Troubleshoot technology issues independently and recommend smarter ways of working.
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed