DeliverIt Group is hiring a Lead Executive Assistant to the CEO to serve as the primary operational partner to our founder and CEO while leading and developing our executive support function. 

This is a high-impact role for an experienced executive assistant who brings judgment, discretion, structure, and calm execution to a fast-moving executive office.  

If you’re looking for a role where you can bring order to complexity, support a high-performing executive, and grow into broader leadership over time, we’d love to hear from you. 

Benefits  

• Health insurance 
• Dental insurance  
• Vision insurance  
• 401(k)  
• Paid time off  
• Paid holidays  
• Life insurance  

Why Join Us  

• Direct partnership with the CEO and senior leadership 
• Clear path to expanded scope and responsibility 
• Opportunity to help shape systems and workflows in a growing founder-led organization  
• Long-term growth potential, including broader operational and Chief-of-Staff-style scope  

What You’ll Do  

• Serve as the primary operational partner to the founder and CEO  
• Lead, mentor, and develop the executive support team, including on-site and remote support staff  
• Build, document, and improve standard operating procedures, workflows, and systems for the executive office 
• Manage a complex executive calendar, correspondence, and domestic and international travel  
• Draft communications, reports, presentations, and other materials on behalf of the CEO  
• Coordinate with senior leadership, legal counsel, accountants, vendors, and external partners  
• Take notes in important meetings, track action items, and ensure follow-up items are completed  
• Help maintain smooth day-to-day execution across a fast-moving executive office  
• Provide occasional light personal and household coordination for the CEO as needed  
• Handle highly sensitive and confidential information with discretion, professionalism, and sound judgment  

What We’re Looking For 

• 5+ years of experience supporting a C-suite executive, ideally a CEO, founder, or owner-operator  
• At least 2 years of experience mentoring, training, or supervising administrative support  staff  
• Demonstrated track record of professionalism, confidentiality, and sound judgment under pressure  
• Strong Microsoft 365 skills, including Outlook, Word, Excel, PowerPoint, and Teams  
• Excellent written and verbal communication skills, including the ability to draft on behalf of an executive  
• Comfortable handling protected health information (PHI) in accordance with HIPAA  
• Experience developing and improving SOPs, workflows, and systems  
• Strong organizational skills, follow-through, and ability to manage competing priorities  
• Calm, reliable, and highly effective in a fast-paced environment  

Preferred Qualifications 

• Healthcare, pharmacy, or other regulated industry experience  
• Experience supporting a multi-entity or multi-location organization  
• Spanish fluency  
• Project coordination or Chief-of-Staff-style experience  
• Texas Notary commission, or willingness to obtain one  

Important Note 

This role includes occasional light personal and household coordination for the CEO, such as family calendar overlap, household vendor scheduling, and occasional personal errands. It is not the primary focus of the role, but it is part of the position.