Technical Support Team Lead, Pressable
Automatticcareers · Remote · 2026-06-08
About this role
<p>At <a href="https://pressable.com/">Pressable</a>, a managed <a href="https://wordpress.org/">WordPress</a> hosting service, we’re seeking a dynamic and experienced Team Lead for our growing 24/7 Technical Support team. This role is a “player-coach” position, where you will be instrumental in ensuring our customers receive world-class support while simultaneously elevating the performance and technical growth of your team.</p> <p>As a working manager in a fast-paced environment, your primary focus will be on supporting, coaching, and enabling our team of highly technical Support Engineers. You will manage their day-to-day performance by providing regular coaching and performance feedback. You will accurately track various metrics and SLAs to ensure that our customer-facing standards are met, and work&nbsp; with leadership to develop and implement new support initiatives. As this is a hybrid role, you’ll also be expected to work in our support queue as needed, responding to customer inquiries through email-based tickets and live chats.</p> <p>You will also work cross-functionally with our Sales, Product, and broader Automattic teams to provide seamless solutions and relay valuable customer feedback to inform future development.</p> <h4>Responsibilities:</h4> <ul> <li>Manage, mentor, and develop a team of Technical Support Engineers, fostering a collaborative and high-performing environment that provides a world-class experience for our customers.</li> <li>Set clear performance goals and expectations, and ensure they are met by regularly assessing individual and team performance, as well as providing timely feedback and coaching.</li> <li>Lead by example as a player-coach, directly engaging with customers by answering complex technical questions, performing website performance audits, and migrating customer websites.&nbsp;</li> <li>Serve as a point of escalation, resolving complex or difficult customer interactions in a positive way.</li> <li>Identify, develop, and implement new strategies to drive improvements in customer satisfaction, team efficiency, and the overall quality of our product offering.</li> <li>Actively monitor and report on the performance of our support team to ensure standards, policies, and SLAs are consistently met or exceeded.</li> <li>Create and deliver training programs and materials to enhance the technical and customer-facing skills of the team.</li> <li>Manage scheduling, including reviewing and approving time-off requests, adjusting schedules for coverage, and arranging extra coverage from third-party contractors.</li> <li>Collaborate with the Head of Support to design and implement changes based on the needs of the department, the company, and our customers.</li> <li>Conduct scheduled one-on-one meetings with your team, taking time to connect with them as well as providing feedback and coaching to help them further develop in their career.</li> </ul> <h4>About You:</h4> <ul> <li>You are a results-oriented leader with a passion for customer support and team development.</li> <li>You thrive in a dynamic start-up environment and are comfortable wearing multiple hats.</li> <li>You possess a strong understanding of how to effectively interact with customers, how to create amazing customer interactions, and how to coach and motivate others.</li> <li>You have a deep technical background in both WordPress and Hosting.</li> <li>You have a proven track record of managing high-performing teams.</li> <li>Your communication and interpersonal skills are exceptional, enabling you to build strong relationships with both internal and external stakeholders.</li> <li>You are proactive, organized, and possess excellent problem-solving and decision-making abilities.</li> </ul> <h4>In addition, you have experience with:</h4> <ul> <li>Leading and motivating technical teams to achieve and exceed performance targets.</li> <li>Developing and implementing customer support strategies that create happy customers and enable efficient scaling.</li> <li>Building and scaling processes and training programs within a technical organization.</li> <li>Leveraging AI to solve problems, build tools, and increase your productivity.</li> <li>Working effectively in a cross-functional environment, collaborating with Sales, Support, and Product teams.</li> <li>Analyzing customer data to identify trends and insights that inform strategic decision-making.</li> <li>Managing and resolving complex customer escalations.</li> <li>WordPress development and a deep understanding of managed hosting services.</li> <li>Excellent verbal and written communication skills, with the ability to present technical information to both technical and non-technical audiences.</li> <li>Strong organizational and project management skills.</li> </ul> <h4>About Pressable&nbsp;</h4> <p>Founded in 2010, Pressable is a world-class managed WordPress hosting provider that specializes in scalable, highly available services for agencies, builders, developers, and businesses.</p> <p>With industry-leading performance, 24/7 expert support, an award-winning control panel, advanced developer tools, and seamless integrations with <a href="https://woocommerce.com/">WooCommerce</a> and <a href="https://jetpack.com/">Jetpack</a>, Pressable provides the tools you need to reliably manage your WordPress websites with ease.</p> <p><strong>We are currently looking for candidates in…
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