Technical Support Specialist

Job Summary Company Overview Squirrels is a globally recognized creator of cutting-edge screen mirroring and digital signage software, with a focus on making wireless communication easier for schools and businesses. Role Overview We are looking for a highly skilled, customer-oriented, and resourceful Technical Support Specialist to take ownership of technical support at our company. This is a unique opportunity for someone who enjoys solving a wide variety of technical problems, working independently, and having a direct impact on both our customers and our internal team. This is a solo operator position. You will be the primary owner of the technical support function and will have significant autonomy over how support operates and evolves. That includes external customer support, internal technical support, ticketing workflows, live chat, phone support, documentation, support tooling, and the processes we use to identify, prioritize, escalate, and resolve technical issues. Rather than joining a large support organization with narrowly defined responsibilities, you’ll have the opportunity to shape the function yourself. We’re looking for someone with broad technical aptitude who is comfortable learning new systems, investigating unfamiliar problems, and figuring things out. You don’t need to be deeply specialized in one particular technical discipline. Curiosity, resourcefulness, technical range, and the ability to solve problems independently are especially valuable in this role. In this role, you will provide exceptional technical assistance to our customers, ensuring they can effectively utilize our screen mirroring and digital signage software. You will troubleshoot and resolve technical issues, guide users through setup and usage, and escalate complex problems as necessary. The ability to understand and explain complex scenarios to a wide range of audiences is a must. The ideal candidate has strong problem-solving skills and a passion for customer service. This is also an AI-first role. We expect you to actively use AI tools as part of your day-to-day work to investigate issues, improve efficiency, create and maintain documentation, analyze support trends, automate repetitive work, and continuously improve how support is delivered. You’ll also have the opportunity to identify and implement AI-assisted support strategies that directly improve the customer experience. We’re looking for someone who sees AI as a practical tool for getting better work done, not simply another piece of software to learn. Because you will have significant ownership of technical support, this role offers substantial room to make an impact, develop new capabilities, introduce better systems, and grow alongside the company. Job Description Key Responsibilities Serve as the primary point of contact for customers experiencing technical issues with screen mirroring software, addressing problems related to connectivity, compatibility, and performance.Own the day-to-day technical support function across customer and internal support, including tickets, email, live chat, phone calls, support workflows, and related processes.Take responsibility for evaluating and improving how technical support is delivered, including the tools, workflows, escalation paths, documentation, and processes used to support customers and employees.Provide troubleshooting assistance via email, phone, or chat, guiding users through diagnostic steps and resolving issues in a timely manner.Diagnose and resolve customer problems with device compatibility, software configuration, network settings, and security/firewall issues.Escalate more complex issues to the appropriate internal teams when necessary and track the resolution progress for customer follow up.Assist customers with the initial installation and configuration of software, ensuring smooth setup on various devices (tvOS, Windows, macOS, etc).Provide step-by-step support for users during the installation process, helping to resolve any issues related to system requirements, device pairing, and network configuration.Help customers configure advanced features, such as multi-device mirroring, screen sharing with audio, and integration with third-party tools (e.g., conferencing platforms).Contribute to and maintain the internal knowledge base by documenting common technical issues, resolutions, and best practices.Update and create new troubleshooting guides, FAQs, and tutorials to help users self-resolve issues and maximize their use of the software.Regularly review and improve support documentation based on feedback and recurring customer inquiries.Communicate recurring technical issues, bugs, or feature requests to the Product and Engineering teams to help improve the software.Provide input on software usability based on customer feedback and technical support insights, contributing to ongoing product enhancements.Guide customers through product features, explaining how to best use the software to meet their specific needs.Use AI tools as a regular part of technical support work, including troubleshooting, research, documentation, communication, analysis, and process improvement.Identify opportunities to use AI and automation to improve support efficiency, response quality, self-service resources, and the overall customer experience.Experiment with and implement new support tools, AI-assisted workflows, and processes when they can meaningfully improve how technical support operates.Act as the internal owner and advocate for technical support, using patterns from customer interactions to identify opportunities for improvements across Support, Product, Engineering, and the broader organization. Key Qualifications Experience: 1+ years of experience in a technical support role, preferably in the SaaS industry. Experience with screen mirroring or collaboration software is a plus.Technical Knowledge: Strong understanding of networking concepts, device compatibility, screen mirroring technology, and troubleshooting methods.Communication Skills: Excellent written and verbal communication skills, with the ability to explain technical concepts to non-technical users in a clear and empathetic manner.Problem-Solving: Strong analytical skills with the ability to diagnose complex technical issues and find effective solutions quickly.Customer-Focused: A passion for helping customers succeed and providing outstanding service, with a track record of building positive relationships.Tools: Experience with customer support platforms (e.g., Zendesk, Freshdesk, Jira).Technical Proficiency: Familiarity with various operating systems (Windows, macOS), mobile devices (iOS, Android), and AppleTV. Knowledge of networking protocols (TCP/IP, DNS, firewall settings) and troubleshooting techniques is essential.Ownership: Comfortable working independently and taking responsibility for an entire functional area, including identifying problems and opportunities without waiting for them to be assigned.Technical Curiosity: Broad technical aptitude and a willingness to learn unfamiliar technologies, systems, and tools. We value someone who can confidently investigate and solve new types of problems over someone whose experience is limited to a single technical specialty.AI Fluency: Comfortable using modern AI tools to accelerate research, troubleshooting, communication, documentation, and other day-to-day work. You should be interested in continually finding new ways to apply AI to improve both your own effectiveness and the customer experience.Initiative: Ability to recognize when a process, tool, or workflow could be better and take the initiative to investigate and implement improvements. Why This Role Is Different This isn’t a role where you’ll inherit a narrow queue of tickets and spend your days following someone else’s support playbook. You’ll own the playbook. You’ll be the person responsible for how technical support works at the company, from helping an individual customer troubleshoot a difficult networking problem to deciding how tickets should be handled, improving documentation, introducing automation, experimenting with AI-assisted support, and bringing recurring customer issues back to Product and Engineering. That makes this role particularly well suited to a technical generalist: someone who likes understanding how things work, isn’t intimidated by unfamiliar problems, and would rather have broad ownership than specialize in one small piece of a larger organization. You’ll have the autonomy to improve the function, the opportunity to see the direct results of your work, and room to expand your responsibilities as the company and its support needs grow. Worker Type Regular Number Of Openings Available 1