About Sensei

Sensei is here to guide you towards greater wellbeing. Founded by Dr. David Agus and Larry Ellison, our ecosystem of products and experiences is designed with one intention: to empower you to grow well. What guides us is a belief that knowledge is the greatest tool in health, and that technology allows us to unlock deeper insights. 

Everything we do is evidence-led, radically transparent, always enriching. 

You can read our story here or see some recent press: Forbes, Condé Nast Traveler.

Position Description 

Sensei is seeking a highly skilled Lead IT Support Specialist to join our team.

As Sensei’s Lead IT Support Specialist, you are responsible for supporting Sensei’s operations on the Hawaiian island of Lānaʻi in all IT areas, providing superior customer service and educating the Sensei team on products and services to ensure everyone is up-to-date on Sensei technology enabling them to support Sensei’s guests and other team members. You will report to Sensei’s IT Manager and be part of the Shared Technology Services team. Additionally, you will work on software deployments, ongoing maintenance, configuration, testing, and troubleshooting.


  • Provide superior customer service to our users through problem resolution and process demonstration
  • Educate and train users as part of ticket resolution and proactively as part of regular training to reduce reoccurring issues
  • Write and publish knowledge base articles, user training materials, and technical documentation and update for accuracy on a regular basis
  • Deploy, install, configure, and/or maintain computer and network hardware and software
  • Maintain detailed records of hardware, software and peripheral configurations
  • Proactively assess the needs of users and make product or process recommendations, especially for common or repeat problems
  • Plan and implement hardware and software deployment and upgrade plans as directed by the IT Manager

Minimum Qualifications

  • 3 years of experience in user support and training role
  • 3 years of experience managing Apple and Windows systems including peripherals such as printers
  • Experience using cloud-based business infrastructure such as G Suite or Microsoft 365
  • Experience using SaaS tools to support IT operations including MDM, ticketing, identity management, knowledge management systems
  • Excellent written and verbal communication skills
  • Highly self-motivated and comfortable in an independent and proactive role with minimal supervision
  • Ability to multi-task and manage multiple simultaneous requests in a ticketing system while prioritizing work based on immediate business needs
  • Demonstrates initiative for continuous technical improvement
  • Valid Driver's License
  • Willingness to work flexible shifts and schedule including weekends, nights, and holidays
  • Willingness to relocate to Lanai City, Hawaii

Desired Qualifications

  • 5 years of experience in a mixed support and engineering role
  • Experience with managing a small team
  • General understanding of enterprise networks
  • Experience with inventory and asset management
  • Specific experience with one or more of the following: Microsoft 365, Okta, Asana, Atlassian suite of tools, Zendesk, Jamf Pro, Kandji
  • Experience with researching and deploying new software or hardware to meet business needs
  • Applicable IT certifications

Sensei Values

  • Loves a good challenge
  • Resourceful and adaptable
  • A strong sense of curiosity
  • Embraces feedback and constantly seeks to improve
  • Collaborative and knows how to get things done as part of a team

Compensation & Benefits

  • Competitive salary
  • Full medical, dental, and vision insurance
  • 401k and FSA plans
  • Subsidized gym membership
  • Cell phone bill reimbursement

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