Executive Assistant to the CEO jobs in United States
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Holladay Ventures · 1 week ago

Executive Assistant to the CEO

Holladay Ventures is seeking a high-performing, technology-forward Executive Assistant (EA) to the CEO, Evan Holladay. This role involves serving as a trusted partner to increase the CEO’s capacity and effectiveness by managing complex tasks, leading special projects, and improving productivity systems.

Property DevelopmentReal EstateReal Estate Investment

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

Qualification

Executive Assistant experienceTechnology proficiencyProject managementCommunication skillsOrganizational skillsDiscretionEmotional intelligenceIntegrityFlexibilityAdaptability

Required

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)

Company

Holladay Ventures

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Holladay Ventures is a real estate development and investment company.

Funding

Current Stage
Early Stage

Leadership Team

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Evan Holladay
Founder and CEO
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Company data provided by crunchbase