Executive Assistant to the CEO

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. 

Key Responsibilities 

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, ClickUp, 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 

Qualifications 

• 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). 
  
  

Core Values & Ideal Attributes 

• 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. 
  

What Makes a Great EA at Holladay Ventures 

• 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.