About OpenSesame 

OpenSesame is disrupting the workforce development industry, leveraging an AI-powered marketplace of more than 50,000 skills courses, complemented by assessments, content authoring, curation, personalized learning pathways, and virtual coaching. eLearning is delivered seamlessly through existing enterprise systems and in the flow of work. More than 2,000 companies, including 150+ of the Global2000, rely on OpenSesame to develop the world’s most productive and admired workforces.

www.opensesame.com/about.

About the Team

The IT team at OpenSesame keeps our employees productive by providing responsive, high-quality technical support. We work across the organization to resolve issues quickly, manage systems efficiently, and continuously improve the employee technology experience. Our team values collaboration, customer focus, and reliability.

About the Job

As a Help Desk Support Specialist, you’ll be the first point of contact for investigating, troubleshooting, and resolving technical issues, managing user access, and setting up hardware and software. You’ll support employee onboarding, maintain support documentation, and help ensure smooth day-to-day operations across a primarily remote workforce.

This role requires strong communication skills, attention to detail, ownership of issues through resolution, and the ability to support non-technical users in a fast-paced environment. Success in this role depends on the ability to independently gather information, follow a structured troubleshooting process, and provide clear documentation and communication throughout the support lifecycle. The ideal candidate is comfortable working through ambiguity, identifying root causes, and performing thorough investigation before escalating issues when appropriate.

Performance-Based Objectives

Within 30 Days

• Complete onboarding and demonstrate proficiency with OpenSesame’s ticketing system, IT documentation tools, and support workflows.
• Shadow hardware and software deployment activities, including workstation setup and user account provisioning.
• Resolve at least 20 Tier 1 IT support tickets, ensuring adherence to internal documentation and defined SLA standards.
• Demonstrate effective ticket documentation, including accurate issue descriptions, troubleshooting notes, and resolution details.

Within 60 Days

• Independently resolve an average of 15 IT support tickets per week, handling hardware, software, and login-related issues.
• Complete 100% of user account requests within one business day of receipt.
• Demonstrate consistent troubleshooting methodology by gathering complete diagnostic information, documenting investigation steps, and identifying likely causes before escalation.
• Update at least 3 knowledge base articles internal documentation to reflect current procedures and reduce repeat support requests.

Within 90 Days

• Increase to an average of 30 resolved support tickets per week, maintaining a 90% SLA compliance rate for Tier 1 tickets.
• Lead at least one IT onboarding session for a new employee, covering essential tools and support processes.
• Identify at least one recurring technical issue, document its impact, and propose a prevention or resolution plan in collaboration with Systems Engineering where appropriate.
• Consistently provide complete escalation documentation that includes troubleshooting performed, relevant system information, and supporting evidence when engineering assistance is required.

Within 120 Days

• Sustain an average of 50 resolved support tickets per week, balancing ticket resolution with onboarding support and documentation responsibilities, with consistent SLA adherence and positive user feedback.
• Deliver a peer training session on a key IT tool, application, or support process.
• Actively contribute to one internal IT process improvement initiative, such as refining onboarding workflows, improving support documentation, enhancing triage practices, or streamlining hardware deployment processes.
• Demonstrate the ability to independently resolve the majority of routine support requests while minimizing unnecessary escalations.

By 6 Months

• Demonstrate full autonomy in managing support, including hardware/software troubleshooting and user lifecycle management, identity and access issues, and endpoint support.
• Maintain high accuracy and completeness in logging and closing tickets in the system, and continue contributing to team knowledge-sharing and documentation.
• Maintain strong end-user satisfaction through clear, timely, and effective communication.
• Demonstrate sound judgment regarding issue prioritization, troubleshooting, and escalation decisions.
• Continue contributing to team knowledge-sharing, process improvements, and documentation.

Tech Stack

• OKTA
• Apple Macbook
• Google Workspace (GSuite)
• Jira
• Confluence
• Zoom
• Microsoft Intune
• JAMF
• Password Manager

Location: This is a remote-first role based in Mexico or Argentina. 

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, and we're highly selective about who we hire. We don't focus on typical job requirements, instead, we're interested in specific examples from your past experiences.

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance