Level 2 Technical Support Specialist

Customer Support Team LeadRequired Skills & Experience: High School diploma required, bachelor's degree preferred in Information Systems, Business, Operations, or related field; equivalent experience considered. Technical certifications in relevant platforms or disciplines are a plus. HubSpot Service Hub certification required at time of hire or within 90 days of start date. Experience: 3–5 years in a technical support, customer support, or implementation support role preferably within a SaaS environment. Demonstrated experience handling complex, multi-layered support issues that require genuine technical investigation, not just script-following. Experience building or significantly contributing to support documentation, knowledge bases, or internal playbooks. Background supporting enterprise or mid-market B2B customers with high operational stakes. Bonus: Prior experience in fleet technology, telematics, logistics software, asset tracking, or industrial SaaS.Technical Skills: Comfortable working at the technical layer of a SaaS platform: understanding data flows, diagnosing configuration issues, and reading API behavior without needing Engineering on every call. Some familiarity with REST APIs, webhook configurations, and basic integration troubleshooting. Mobile application support experience; IoT device familiarity is a strong plus given the fleet context. Proficiency in support ticketing platforms. Proficiency in CRM platforms, HubSpot strongly preferred. Competency in knowledge base and documentation tools. Comfortable working with browser developer tools, log files, and basic diagnostic outputs to investigate reported issues is a plus.Competencies & Characteristics: Customer service ninja: You don't just resolve tickets you leave customers genuinely impressed. Your interactions are responsive, clear, patient, and human. People feel helped when they talk to you. Technical depth with communication clarity: You understand complex systems and you can explain them simply. You never hide behind jargon, and you never oversimplify to the point of being unhelpful. Builder: You encounter a gap in documentation, and you fill it. You see a recurring issue, and you suggest a process to address it. You don't wait to be told you identify what's needed and you build it. Investigative rigor: When something breaks, you want to understand exactly why, not just enough to close the ticket, but enough to explain it, document it, and prevent the next one. Process-oriented: Your tickets are organized, your documentation is structured, and your escalations are clean. You bring order to complexity without losing responsiveness. Calm under pressure: A fleet operator with an active operational disruption needs someone who communicates with calm, clear authority. That's you — even when the issue is hard. Collaborative: You share what you know. You ask for help when you need it. And you make the people around you better by working with them.Job Description: The Customer Support Team Lead is a senior individual contributor and subject matter expert responsible for delivering exceptional, technically credible support across our customer base. Reporting to the Director of Customer Success, this role is not a people manager, but it is absolutely a leader. You will be the most knowledgeable support resource in the building, the person the team turns to when a ticket gets hard, and the person customers come to trust when something goes wrong. You will provide direct, hands-on support coverage while simultaneously building the knowledge infrastructure the entire support function will operate on: knowledge base content, FAQ libraries, escalation workflows, troubleshooting guides, and bug documentation processes. You will investigate issues deeply, understand them completely, and communicate them clearly to customers, to teammates, and to Product and Engineering. This is a ground-level, in-the-guts-of-the-product role. You will know this platform better than almost anyone. And you will use that knowledge to deliver a support experience that customers in this industry have simply never encountered before.The Role: We are looking for the founding member of our front-line support crew. Only customer champions, advocates, ninjas, or legends need apply. The Customer Support Team Lead is the standard-setter. You are not here to close tickets. You are here to solve problems completely, clearly, and in a way that leaves the customer more capable and more confident than they were before they reached out. You'll handle the full spectrum of support: product bugs, configuration questions, user issues, integration troubleshooting, and escalation triage. You'll be the SME your teammates bring their hardest questions to. When you don't have the answer, you'll know exactly how to find it and you'll document it so the next time, someone on the team does. You are building something here. The knowledge base, the support playbook, the escalation framework, none of it exists yet at the level it needs to. That is not a problem. That is your opportunity.Why This Role Matters: Fleet operators run 24/7 operations. When something breaks or stops working as expected, it's not an inconvenience, it's an operational disruption. The experience they receive in those moments determine whether they feel like they made the right purchase decision or the wrong one. One of the most consistent and damaging complaints in technology is that support after the sale is slow, generic, and handled by people who don't actually understand the product. We are going to be the exception to that rule, and this role is the reason why. The Customer Support Team Lead sets the tone, helps to build the infrastructure, and personally demonstrates what legendary customer experience and expert support looks like in this industry.