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Director of Sales Engineers (Automattic for Agencies)

July 15, 2026

Automattic for Agencies (A4A) is dedicated to helping agencies and developers succeed by providing them with the tools, hosting, and expert support needed to create exceptional WordPress experiences. As a senior leader within Automattic for Agencies, you will partner with executive leadership to shape and execute strategies that position A4A as a market leader for agency solutions. You will be responsible for guiding and empowering a high-performing team to drive growth by converting agency prospects into customers, delivering a world-class onboarding experience, retaining small-to-medium business (SMB) customers, and creating a differentiated customer support experience for agencies.

Key Responsibilities:

Vision and Strategy Development:

Develop and articulate the long-term vision for the Sales Engineering function, aligning team goals with Automattic for Agencies’ overall business objectives.
Drive organizational improvements to Sales Engineering processes, setting benchmarks and establishing industry-leading practices for customer engagement and success.

Team Leadership & Development:

Lead and mentor a team of Sales Engineers to achieve individual and team performance goals.
Foster a collaborative, inclusive, and high-performing global team culture.
Provide regular coaching, feedback, and professional development opportunities to team members.
Design and execute a roadmap for scaling the Sales Engineering team to support growth, including identifying skill gaps, recruiting talent, and optimizing team structure for efficiency and impact.

Customer Acquisition & Retention:

Support Sales Engineers in developing consultative sales approaches to convert agencies into A4A program members.
Ensure the team delivers exceptional onboarding experiences, equipping agencies with the knowledge and tools to succeed.
Drive initiatives to retain SMB customers and maximize lifetime value (LTV) through a maintainable and scalable approach.
Act as a senior advocate for agency customers, influencing product roadmaps and company priorities based on insights from the Sales Engineering team and customer feedback.

Operational Excellence:

Define and track key performance metrics for the team, ensuring alignment with company goals.
Oversee the development and execution of efficient workflows for customer acquisition, onboarding, support, and retention.
Collaborate with Sales Engineers to troubleshoot onboarding issues, support trends, and escalate systemic challenges as needed.

Cross-Functional Collaboration:

Lead cross-functional initiatives to innovate customer acquisition, onboarding, and retention strategies, ensuring alignment across all A4A teams.
Represent the Sales Engineering team in discussions around product improvements, feature requests, and overall customer satisfaction.

Support Experience Innovation:

Lead efforts to deliver a differentiated support experience for A4A customers, ensuring seamless interactions and personalized solutions.
Actively identify opportunities for process improvement, automation, and enhanced customer engagement strategies.

Requirements:

Proven experience leading a team in sales, technical support, or customer success roles, preferably in the technology or SaaS space.
Strong understanding of consultative sales techniques and customer onboarding best practices.
Exceptional communication and collaboration skills, with the ability to inspire and motivate team members.
Proven ability to establish team structures, workflows, and performance metrics to support business growth and operational excellence.
Demonstrated ability to manage competing priorities and deliver results in a fast-paced, remote-first environment.
Technical acumen with experience troubleshooting technical systems and aligning solutions with customer needs.
Proven experience in developing a successful customer relationship motion that results in high lifetime value (LTV).
Strong analytical skills with experience using data to inform decision-making and measure success.
Empathy, adaptability, and a commitment to delivering outstanding customer experiences.

Key Measurements of Success:

Team performance in meeting or exceeding customer acquisition, onboarding, and retention goals.
Success in establishing scalable, repeatable systems for customer acquisition and retention, contributing directly to A4A program growth and customer satisfaction.
Customer satisfaction metrics, including onboarding success.
Individual development and performance of team members.
Quality and effectiveness of collaboration with cross-functional teams.

Salary range: $90,000-$125,000 USD. Please note that salary ranges are global, regardless of location, and we pay in local currency.

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

This isn’t your typical work-from-home job—we are a fully-remote company with an open vacation policy. Read more about our compensation philosophy. To see a full list of benefits by country, consult our Benefits Page. And check out these links to learn more about How We Hire and What We Expect from Ourselves.

About Automattic

We’re the people behind WordPress.com, WooCommerce, Tumblr, Simplenote, Jetpack, Longreads, Day One, PocketCasts, and more. We believe in making the web a better place.

We’re a distributed company with more than 1700 Automatticians in nearly every corner of the globe, speaking over a hundred different languages. Enriched by this diversity, we’re united by a singular mission: to democratize publishing, commerce, and messaging so anyone with a story can tell it, anyone with a product can sell it, and everyone can manage their communications from a single source. In short, we help maintain a balance in society, creating and continually refining powerful tools people can use to compete fairly—regardless of income, gender, politics, language, or where they live in the world.

We believe in Open Source, and the vast majority of our work is available under the GPL. Automattic is a Most Loved Company and Disability Confident Committed. (Here’s what that might mean for you.) Learn more about our dedication to diversity, equity, and inclusion and our Employee Resource Groups.

If you need disability-related accommodations during the application or interview process, please fill out this form. We are committed to ensuring an accessible hiring process for all candidates.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...