Helpdesk Manager

About Checkmate

Checkmate is a restaurant technology solution provider that has continually evolved over time. We started in 2017 by integrating 3rd party platforms to the POS systems of restaurants. At that time, there were multiple 3rd party platforms like GrubHub, UberEats, DoorDash, Postmates, Caviar, and even Amazon!

This was the photograph that started it all!

We have since then continually evolved to add multiple products to our portfolio, the primary ones being first party ordering solutions like web and app ordering, kiosks and catering. We have now recently moved into three new exciting products: Digital Menu Boards, Phone Ordering AI and Drive thru AI. We form a very core part of the restaurant technology ecosystem, and are continually adding more and more digital solutions for the restaurant brands to increase their sales.

Our revolutionary enterprise menu management system, Everyware, truly unlocks the potential of menus and how it can be customized for each individual digital channel. As you can see, this is a company that continually evolves and adapts and today we are powering digital ordering solutions for some of the largest brands in the world.

We have been called the "north star of vendors" as we truly believe that technology is just a method by which we service the customers, it does not form the entirety of it. Service is a big component of what we provide to our customers, which is inherently believed by every single team member here. We are doing a lot of exciting things, including application of AI in our products and systems, using experimentation at scale to determine what works for our clients and ML to analyze and productize the massive amount of data we have. Each individual here makes a difference and has a valuable contribution. Key traits here are ownership and drive. Join us if you think you have them.

About the Role:

We are seeking a Helpdesk Manager to lead and manage our internal IT support operations for a fully remote workforce. This role will be responsible for overseeing the helpdesk ticketing system, supporting employees with technical issues, managing IT processes, and ensuring our distributed team has the tools and systems needed to work effectively.

The ideal candidate is self-starting, highly organized, customer-focused, technically capable, and experienced in supporting remote organizations.

Key Responsibilities

• Manage and prioritize incoming helpdesk tickets and ensure timely resolution of employee support requests.
• Provide technical support to internal users across hardware, SaaS tools, identity management, and collaboration platforms.
• Administer and maintain identity and access management systems (e.g., JumpCloud, Okta, Google Workspace, etc.).
• Oversee onboarding and offboarding processes including device provisioning, account setup, and access management.
• Manage Mac and Windows device lifecycle, including provisioning, security policies, and troubleshooting.
• Maintain documentation for IT policies, troubleshooting guides, and internal knowledge base articles.
• Monitor and improve helpdesk performance metrics such as response times, resolution times, and ticket backlog.
• Coordinate with engineering, security, and operations teams to resolve cross-department technical issues.
• Manage vendor relationships for IT tools, software licenses, and equipment procurement.
• Implement and maintain security best practices for a distributed workforce.
• Continuously improve internal IT systems, automation, and support workflows.

Requirements:
• 5+ years of experience in IT support, helpdesk management, or systems administration.
• 5+ years of experience providing support for a Google Workspace based organization
• 3+ years of experience working with Apple Business Manager
• Experience supporting remote or distributed organizations.
• Experience implementing MDM solutions for remote device management (JumpCloud, Jamf).
• Strong experience with MacOS, Windows and common business SaaS tools.
• Experience with helpdesk ticketing platforms (Asana, Jira Service Management, Zendesk, Freshservice, etc.).
• Experience managing identity and device management platforms (JumpCloud, Google Workspace, etc.).
• Strong troubleshooting skills across hardware, networking, and SaaS applications.
• Excellent communication skills with the ability to support non-technical users.
• Highly organized with the ability to prioritize and manage multiple requests simultaneously.
• Must be comfortable working in US hours at least till 5 pm EST

Preferred Qualifications

• Familiarity with security frameworks and access management best practices.
• Experience working in high-growth technology companies or startups.
• Knowledge of automation tools such as Zapier, scripting, or workflow automation.