Technical Support Team Lead

Automattic

Technical Support Team Lead at Pressable overseeing a 24/7 support team. Responsible for customer interactions and team performance development in a fast-paced environment.

Posted 6/8/2026full-timeRemote • 🇺🇸 United StatesSenior💰 $40,000 - $60,000 per yearWebsite

Tech Stack

Tools & technologies

WordPress

About the role

Key responsibilities & impact

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.
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.
Lead by example as a player-coach, directly engaging with customers by answering complex technical questions, performing website performance audits, and migrating customer websites.
Serve as a point of escalation, resolving complex or difficult customer interactions in a positive way.
Identify, develop, and implement new strategies to drive improvements in customer satisfaction, team efficiency, and the overall quality of our product offering.
Actively monitor and report on the performance of our support team to ensure standards, policies, and SLAs are consistently met or exceeded.
Create and deliver training programs and materials to enhance the technical and customer-facing skills of the team.
Manage scheduling, including reviewing and approving time-off requests, adjusting schedules for coverage, and arranging extra coverage from third-party contractors.
Collaborate with the Head of Support to design and implement changes based on the needs of the department, the company, and our customers.
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.

Requirements

What you’ll need

You are a results-oriented leader with a passion for customer support and team development.
You thrive in a dynamic start-up environment and are comfortable wearing multiple hats.
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.
You have a deep technical background in both WordPress and Hosting.
You have a proven track record of managing high-performing teams.
Your communication and interpersonal skills are exceptional, enabling you to build strong relationships with both internal and external stakeholders.
You are proactive, organized, and possess excellent problem-solving and decision-making abilities.
Leading and motivating technical teams to achieve and exceed performance targets.
Developing and implementing customer support strategies that create happy customers and enable efficient scaling.
Building and scaling processes and training programs within a technical organization.
Leveraging AI to solve problems, build tools, and increase your productivity.
Working effectively in a cross-functional environment, collaborating with Sales, Support, and Product teams.
Analyzing customer data to identify trends and insights that inform strategic decision-making.
Managing and resolving complex customer escalations.
WordPress development and a deep understanding of managed hosting services.
Excellent verbal and written communication skills, with the ability to present technical information to both technical and non-technical audiences.
Strong organizational and project management skills.

Benefits

Comp & perks

Health Benefits for US-based staff (99% Paid Employee Medical, Dental, and Vision).
Matching 401(k) for US-based staff.
Life and Disability Insurance for US-based staff (100% Paid Life, & LTD).
Work from home with home office setup and coworking allowances.
Open vacation policy (no set number of days per year).
Hardware and software, books or conferences that promote continued learning.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

WordPressHostingwebsite performance auditscustomer support strategiesAI problem-solvingdata analysisproject managementtraining program developmentperformance assessmenttechnical coaching

Soft Skills

leadershipteam developmentcommunicationinterpersonal skillsproblem-solvingdecision-makingorganizationcollaborationmotivationcustomer interaction