Executive Assistant to CEO – Healthcare in Sugar Land, Texas at DeliverIt Holdings and Investments Inc

Lead the executive support function for a founder/CEO running one of Houston's fastest-growing healthcare and pharmacy organizations.

DeliverIt® Group is hiring an exceptional Lead Executive Assistant to serve as the primary operational partner to our founder and CEO — and to lead, mentor, and develop our small executive support team. This is a senior, supervisory role at a privately held, multi-entity healthcare and pharmacy organization headquartered in Sugar Land. We are looking for someone who wants a long-term home and a path to growing into broader scope over time, not a stepping stone.

If you are an experienced EA or executive support lead who thrives on complexity, takes pride in being the steady hand behind a busy executive, and has the judgment to develop a team underneath you — read on.

About DeliverIt® Group

Founded in 2011, DeliverIt® Group is a privately held, founder-led healthcare organization with operations across Greater Houston. Our entities include retail pharmacies, a closed-door specialty pharmacy licensed in multiple states, an ambulatory infusion center, and a 503B sterile compounding facility currently under development. We are entering our most exciting chapter yet — and the right EA will be in the room for it.

Health, dental, vision insurances, 401(k), PTO accrual, paid holidays, life insurance

• Direct partnership with the CEO and senior leadership.

• A clear growth path toward expanded scope and responsibility.

• A stable, long-term home in a founder-led organization that is still growing.

What You'll Do

• Serve as the primary operational partner to the CEO of a multi-entity healthcare organization.

• Lead, mentor, and develop the executive support team, including a junior on-site assistant and remote executive support.

• Build and own standard operating procedures, workflows, and systems for the executive office.

• Manage a complex executive calendar, correspondence, and domestic and international travel.

• Draft communications, prepare reports and presentations, and keep the CEO two steps ahead.

• Coordinate with senior leadership, legal counsel, accountants, vendors, and external partners on the CEO's behalf.

• Take notes in high-stakes meetings, track follow-ups, and quietly make sure nothing slips.

• Provide light personal and lifestyle coordination as needed (we're honest about this — see note below).

• Operate with discretion in a regulated environment where confidentiality is non-negotiable.

What We're Looking For

• 5+ years supporting a C-suite executive (CEO, founder, or owner-operator preferred), including at least 2 years mentoring, training, or supervising other administrative staff.

• A verifiable track record of confidentiality and sound judgment under pressure.

• Fluency in Microsoft 365 (Outlook, Word, Excel, PowerPoint, Teams).

• Exceptional written and verbal communication, with the ability to draft on the CEO's behalf.

• Comfort handling protected health information (PHI) per HIPAA.

• Demonstrated ability to develop standard operating procedures, workflows, and systems.

• The leadership presence to coach a junior team member and the candor to flag when something isn't working.

• Reliable, consistent, and unbothered by a fast pace.

Nice to Have

• Healthcare, pharmacy, or other regulated industry experience.

• Multi-entity or multi-location organizational experience.

• Spanish fluency.

• Project coordination or Chief-of-Staff-style experience.

• Texas Notary commission (or willingness to obtain one).

One Honest Note

This role includes occasional light personal and household coordination for the CEO (family calendar overlap, household vendor scheduling, occasional personal errands). It is not the main focus of the job, but it is part of the job. We mention it now so there are no surprises in month two.

Growth Path

This role is designed to grow. The right candidate will start as Lead Executive Assistant, demonstrate impact in the first 6–12 months, and have a real path toward expanded scope — potentially including Chief-of-Staff-style responsibilities, operational projects, and broader corporate support as DeliverIt continues to grow. We are looking for someone who wants to build a career here, not pass through.