Back to jobs
New

Technical Support Team Lead

Remote

At Pressable, a managed WordPress 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.

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  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.

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.

Responsibilities:

  • 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.

About You:

  • 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.

In addition, you have experience with:

  • 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.

About Pressable 

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.

With industry-leading performance, 24/7 expert support, an award-winning control panel, advanced developer tools, and seamless integrations with WooCommerce and Jetpack, Pressable provides the tools you need to reliably manage your WordPress websites with ease.

We are currently looking for candidates in Latin America and North America only.

Salary range: $40,000 -$60,000 USD. Please note that while salary ranges are presented here in USD, we will pay in local currency.

We are searching for high-caliber candidates with the skills and qualities to have a net positive for Pressable. Pay will reflect the potential contribution and the impact you can bring, which may, in some cases, go beyond the range stated for the right candidate.

Perks & Benefits of Joining Pressable!

  • 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.

Check out these links to learn more about How We Hire and What We Expect from Ourselves. 

So, are you ready to embark on this thrilling WordPress adventure? We can’t wait to welcome you to the Pressable team and empower you to make the web a better place. Come join us in crafting an exceptional customer experience and revolutionizing the world of WordPress hosting. Apply now and let’s build something amazing together!

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...
Select...
Select...
Select...

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Pressable’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.

We use Greenhouse’s AI-powered Talent Matching tool to compare your application against our job requirements.

Learn more