Executive Assistant to the CEO and IT Operations Generalist

Position Summary

We are seeking a highly capable Executive Assistant to the CEO with genuine hands-on experience in information technology.

This is not a traditional administrative assistant position. The successful candidate will operate as a versatile cross-functional professional who can support executive priorities, understand technical systems, investigate problems, coordinate projects, document processes, and assist with IT and compliance operations.

Candidates should have previous experience in real technical roles such as System Administrator, IT Support Specialist, Software Tester, QA Analyst, QC Tester, Technical Project Coordinator, Application Support Specialist, or a similar position.

The selected candidate will receive additional training in regulatory compliance, internal controls, organizational systems, and the responsibilities of the IT department.

Key Responsibilities

Executive Support

• Support the CEO with operational, technical, and administrative priorities.
• Organize projects, follow-ups, deadlines, meetings, and cross-department assignments.
• Convert executive instructions into structured action plans.
• Track completion of tasks and identify delays, risks, and unresolved issues.
• Prepare reports, summaries, documentation, and internal communications.
• Coordinate with employees, vendors, technical teams, and external partners.
• Handle sensitive business and technical information with discretion.

IT and Systems Support

• Assist with user access, system configuration, troubleshooting, testing, and technical documentation.
• Investigate software, hardware, connectivity, and workflow issues.
• Support implementation and testing of new systems, applications, integrations, and automations.
• Perform functional testing, quality assurance, and issue reproduction.
• Document defects clearly and communicate technical findings to vendors or developers.
• Maintain system inventories, access records, change logs, and technical instructions.
• Assist with onboarding and offboarding users from company systems.
• Help ensure that technical processes are organized, repeatable, and properly documented.
• Support the IT department with operational tasks, audits, projects, and system reviews.

Compliance and Process Responsibilities

• Learn and follow applicable compliance, privacy, security, and internal-control requirements.
• Assist with compliance documentation, audit preparation, access reviews, and policy implementation.
• Help create and maintain standard operating procedures, checklists, and process maps.
• Verify that required steps are completed and properly documented.
• Identify operational weaknesses and recommend structured improvements.
• Maintain confidentiality and follow strict information-security practices.

Required Qualifications

• Previous professional experience in a hands-on IT position.
• Practical understanding of computer systems, software, user access, troubleshooting, and technical workflows.
• Experience in system administration, technical support, software testing, QA, QC, application support, or a comparable field.
• Strong analytical and problem-solving skills.
• Ability to approach tasks logically, structurally, and methodically.
• Strong written documentation and communication skills.
• Ability to manage multiple unrelated priorities without losing accuracy.
• Ability to learn unfamiliar systems quickly.
• High level of discretion, reliability, ownership, and professional judgment.
• Ability to work directly with executive leadership and accept rapidly changing priorities.

Preferred Qualifications

• Experience supporting healthcare, education, finance, or another regulated organization.
• Familiarity with compliance, cybersecurity, access control, audit trails, or data privacy.
• Experience working with vendors, developers, software platforms, or technical projects.
• Familiarity with testing methodologies, bug reporting, ticketing systems, and change management.
• Experience writing SOPs, technical instructions, or internal policies.
• Basic understanding of databases, networks, cloud systems, APIs, automation, or software development.

Ideal Candidate

The ideal candidate is a structured and technically minded generalist who can move between executive support, IT operations, testing, documentation, compliance, and project coordination.

This person should be comfortable serving as a reliable operational problem-solver rather than working within a narrowl…