IT Technology Enablement Specialist (Microsoft 365)

TL;DR

IT Technology Enablement Specialist (Microsoft 365): Providing white-glove IT support to executive leadership and driving enterprise-wide adoption of Microsoft 365 tools with an accent on productivity optimization and training delivery. Focus on translating complex technical features into actionable workflows and ensuring seamless technology experiences for senior stakeholders.

Location: San Jose, Costa Rica (Remote)

Company

hirify.global is a global technology company dedicated to providing world-class service and enterprise software solutions.

What you will do

• Provide concierge-level IT support to the Executive Leadership Team, ensuring rapid resolution of complex technical issues.
• Design and deliver training sessions, lunch-and-learns, and practical guidance for Microsoft 365 and enterprise applications.
• Develop reusable training materials, knowledge articles, and best-practice content for the organization.
• Proactively identify opportunities to enhance executive productivity through AI tools and process streamlining.
• Partner with IT, Security, and Business teams to align training with organizational standards.
• Monitor adoption trends and user feedback to continuously improve enablement activities.

Requirements

• Significant experience in an IT support, digital workplace, or technology enablement role within an enterprise environment.
• Strong hands-on knowledge of Microsoft 365, including Outlook, Teams, OneDrive, SharePoint, and Copilot.
• Extensive experience supporting both Windows and macOS applications.
• Proven track record of supporting senior leaders or executives in high-trust environments.
• Demonstrable experience in identifying training needs and delivering effective training programs.
• Excellent communication skills with the ability to explain technology clearly to non-technical audiences.

Nice to have

• Familiarity with executive collaboration patterns and personal productivity workflows.
• Experience working with security and compliance requirements in regulated environments.
• Exposure to AI-assisted productivity tools.
• Microsoft certifications such as MCT, MS-900, or Modern Desktop Administrator.
• Experience with change management frameworks like ADKAR or Prosci.

Culture & Benefits

• Opportunity to work in a fast-paced, global IT organization.
• Commitment to diversity and equal opportunity employment.
• Supportive environment focused on professional growth and high-achieving teams.
• Emphasis on continuous improvement and digital workplace evolution.

Hiring process

• Background and reference checks are part of the hiring process.