# IT Support Specialist II

**Company:** [Openly](https://hotfix.jobs/companies/openly)
**Location:** Remote
**Role:** IT Support
**Salary:** $64k – $107k/yr
**Experience:** 3+ years
**Skills:** it support, Troubleshooting, macOS, Windows, Networking, Okta, Google Workspace, Python, Terraform, Project Management, Documentation, it infrastructure
**Posted:** 2026-07-27

> Mid-level IT Support Specialist providing advanced technical support, infrastructure administration, process improvements, and guidance to junior team members in a remote environment. Requires 3-5 years of IT support experience, strong troubleshooting and networking skills, and familiarity with macOS/Windows, Okta, Google Workspace, Python and Terraform.

## Job Description

## Key Responsibilities
- Provide advanced technical support to end-users, serving as an escalation point for hardware, software, and technology issues that require in-depth troubleshooting and analysis.
- Take ownership of technical challenges, providing guidance to junior team members and collaborating with other IT teams to address and resolve intricate problems.
- Administer and maintain IT infrastructure, including user account management, access control, and other critical systems.
- Identify opportunities to enhance IT support processes and actively implement improvements to increase efficiency and effectiveness.
- Create and maintain comprehensive documentation for IT infrastructure and processes, ensuring knowledge is shared across the team.
- Provide training and guidance to end-users and junior team members on best practices and the use of various hardware and software applications.
- Facilitate the IT onboarding process for new hires by configuring their computers and applications, and serving as their primary point of contact for any initial technical questions.
- Manage IT assets and inventory, from procurement and deployment to tracking and disposal of hardware and software.
- Lead and coordinate small to medium IT projects, leveraging project management methodologies and tools.
- Support and maintain both macOS and Windows environments, staying updated on new technologies and industry trends.
- Effectively communicate technical solutions to both technical and non-technical stakeholders, actively listening to others and ensuring you are understood.

## Requirements
- Associates degree in Information Technology, Computer Science, or a related field, or relevant certifications.
- 3-5 years of experience in an IT support role.
- Awareness of scripting languages (Python), no code automation tools, and infrastructure as code technologies (Terraform).
- In-depth understanding of hardware, software, and IT environments.
- Proven experience in advanced troubleshooting and problem resolution.
- Strong understanding of networking concepts.
- Knowledge of administering and maintaining IT infrastructure including Okta and Google Workspace.
- Proficiency in macOS and Windows environments.
- Ability to implement IT best practices and processes.

## Core Competencies
- Customer Service: A strong commitment to providing prompt and effective support to end-users with a patient and empathetic approach.
- Communication Skills: Communicates clearly and concisely with both technical and non-technical stakeholders, actively listening and ensuring you are understood.
- Documentation: Creates and maintains comprehensive documentation for IT infrastructure and processes, sharing knowledge with the team.
- Process Improvement: Proactively identifies opportunities to enhance IT support processes and implements solutions to increase efficiency.
- Proactive Learning: A strong desire to learn and expand your technical knowledge.
- Collaborative Problem-Solving: Acts as a resource for troubleshooting across the organization, working with other IT teams to address complex issues.

## Perks & Benefits
- Remote-First Culture with flexible, distributed team.
- Competitive Pay & Equity: Top-tier base salary plus ownership in Openly’s growth.
- Comprehensive Health Coverage: Medical, dental, and vision plans.
- Life & Disability Insurance.
- Parental Leave: Up to 8 weeks of paid parental leave.
- 401(k) Company Contribution: 3% of gross income.
- Home Office Setup: $1,500 upfront allowance plus $75/month internet stipend.
- Professional Development: $2,000 annually.
- "Be Well" Program: $50/month stipend.
- Volunteer Hours & Referral Rewards.

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