IT Analyst (AI)

Location: Hybrid in Chicago, Illinois, with in-office support required at least one week per month. Applicants must be able to live and work full-time in one of the listed US states.

Salary: $65,544–$75,000 annually, plus equity.

Company

hirify.global builds technology-enabled homeowners insurance and related products designed to make homeownership simpler and more affordable in areas affected by climate risks and rising costs.

What you will do

• Own Tier 2 helpdesk requests and resolve escalations from Tier 1, routing complex issues to Tier 3 or IT Engineering.
• Manage IT onboarding and offboarding, including access, equipment, and orientation for new hires.
• Provision, deprovision, and audit access in Okta, Google Workspace, Slack, and BetterCloud according to RBAC procedures.
• Maintain device records in Jira Assets and JumpCloud and support the Chicago office’s A/V, badge access, and security needs.
• Document procedures and runbooks in Confluence, identify process friction, and lead workflow improvement and automation projects.
• Train and mentor interns and Junior Analysts while using AI tools such as Claude to improve efficiency.

Requirements

• 2+ years of IT experience, including hands-on Tier 2 and remote-first support.
• Proficiency troubleshooting macOS and Windows.
• Administration experience with Google Workspace, Slack, Okta, JumpCloud, and/or BetterCloud.
• Experience with ticketing systems, especially Jira Service Management, and documenting solutions in Confluence.
• Experience using AI tools such as Claude or ChatGPT for workflow efficiency, or strong aptitude to develop this skill quickly.
• Ability to provide in-office support in Chicago at least one week per month and live and work full-time in an eligible US state.

Culture & Benefits

• Remote-first environment with offices in Chicago and St. Petersburg, Florida for collaboration.
• Company equity through Restricted Stock Units and a 401(k) match of up to 4% of eligible earnings.
• Medical, dental, vision, HSA, life insurance, disability, and supplemental insurance options.
• Flexible PTO for exempt employees, company holidays, and paid parental leave.
• Mental health support, confidential counseling, and professional development budgets for certifications, conferences, and learning.
• Culture focused on ownership, respectful collaboration, lean operations, curiosity, and continuous improvement.

Hiring process

• Interviews with recruiters, hiring managers, and team members.
• A relevant skills assessment may be included.
• Prompt updates and feedback are provided following interviews.