I will build our business sustainably through passionate and loyal customers.

Customers are central to everything we do. The Happiness Engineer title aims to capture how seriously we take that work. In 2007, when Matt Mullenweg posted Automattic’s first Happiness Engineer job listing, he described the role like this:

We consider the support side of the user experience to be vitally important because it is the person who interacts with our customers most and makes the biggest impression in their time of need.

At the time, Matt paid close attention to Tony Hsieh of Zappos, where customer happiness wasn’t merely a metric, it was the whole business. Matt wasn’t going to call it Support. We focus on outcomes at Automattic, and the outcome he wanted was happiness. 

Meanwhile, Automattic at that time was mostly engineers. Matt wanted every person at Automattic on equal footing. When he posted that first job listing for a Happiness Engineer, he did not mean engineer in the sense of code and credentials. He meant engineer in the deepest sense of the word: someone who does not just solve problems but asks whether the problem needed to exist in the first place. The best engineers are not the ones who answer the most tickets. They are the ones who build the solution that means the ticket never gets created again. Helping a small business owner resolve their site’s issue at 2:00 A.M. is as important as writing the code that powers it.

Minutes after the first job listing went live, a colleague wrote back: “Happiness Engineer. I like that.”

Nearly two decades later, so does everyone else. For me, it’s the greatest job title I’ll ever have. It’s aspirational. It inspires me to engineer happiness for the people I serve, whether those people are customers, team members, peers, or other Automatticians. Happiness Engineers debug, investigate, and advocate for customers. They often know more about how our products work in the real world than anyone else in the company.

Build Real WordPress Experience

The most valuable thing you can do is use WordPress. A lot.

• Set up your own site (or several!). WordPress.com lets you create a site for free. Build something real. Break things and fix them. Try different themes. Install plugins. Experiment with the block editor.
• Try WooCommerce. Even setting up a test store and walking through the setup process will teach you a ton about how online stores work on WordPress.
• Troubleshoot on purpose. When something doesn’t work as expected, resist the urge to just search for the answer and move on. Dig in. Look at what’s happening. Try to understand what the root cause of an issue is rather than looking for a simple fix of a symptom. That troubleshooting instinct is exactly what we’re looking for.

Get Into the WordPress Community

• Volunteer in the WordPress.com forums. Start helping other users with their questions. This is essentially practice for the HE role and is a way to showcase some relevant support work. You’ll build WordPress knowledge, develop your support communication skills, and show genuine initiative. If you do this, mention it in your application and link to your profile.
• Attend a WordCamp or WordPress meetup. These are community events where you can connect with other WordPress users, learn from talks and workshops, and immerse yourself in the ecosystem. They’re affordable, welcoming, and a great way to deepen your involvement. You might even find us at a career booth. Come say hello!
• Follow WordPress development and news. Read the WordPress.com blog, follow WooCommerce updates, and stay current with what’s happening in the ecosystem.

Build Your Support Skills

If you don’t have customer support experience yet, find ways to start.

• Freelance or volunteer. Help people with their websites. Offer to troubleshoot for friends or local businesses. Any experience where you’re solving someone else’s technical problem through clear communication counts.
• Practice writing support responses. Find real questions in the WordPress forums and draft responses, even if you don’t post them. Focus on being clear, warm, and thorough without being overwhelming.

Develop Your AI Skills

This is newer territory, and it’s increasingly important.

• Go beyond prompting. If you’ve only used AI to ask questions and get answers, start experimenting with building something. Automate a repetitive task. Create a workflow. Build a tool that solves a real problem.
• Try building with AI coding tools. Tools like Claude Code, GitHub Copilot, or Cursor let you build things even if you’re not a traditional developer. Try shipping a project: a browser extension, a script that automates part of your workflow, a custom tool for something you do regularly.
• Use AI in your WordPress learning. As you’re building sites and troubleshooting, practice using AI as a research partner. Ask it to explain concepts, then verify by testing. Build the habit of understanding what AI tells you, not just accepting it.
• Document what you build. When you apply, you’ll want specific examples. Keep track of the workflows, tools, or processes you’ve created with AI and what impact they had.

Develop Your Technical Foundation

You don’t need to be a developer, but a solid technical foundation goes a long way.

• HTML & CSS basics: MDN Web Docs and freeCodeCamp are excellent free resources.
• Domains & DNS: Cloudflare’s Learning Center explains how the internet works in approachable terms.
• SEO fundamentals: Many customers want to grow their audience. Understanding the basics of how search engines work makes you more helpful.
• eCommerce concepts: If you haven’t run or helped run an online store, even a small test shop will give you useful context.

Resources to Help You Level Up

WordPress Skills

• WordPress.com Learn – Tutorials straight from the source.
• WP Beginner – Great for building foundational knowledge.
• WordPress.tv – Video content from WordCamps and the WordPress community.

HTML & CSS

• MDN Web Docs – Solid, comprehensive tutorials.
• freeCodeCamp – Interactive learning that’s actually free.
• CSS-Tricks – Because CSS can be tricky!

Domains & DNS

• MDN Web Docs DNS Guide – Easy to follow explanations.
• Cloudflare’s Learning Center – Deeper dives when you’re curious.

AI Tools & Learning

• Claude Code – Build projects and automate tasks with AI assistance.
• GitHub Copilot – AI-powered coding that helps you build tools and workflows.
• Cursor – An AI-first code editor, great for learning to build with AI even if you’re not a developer.
• Prompt Engineering Guide – Learn how to get better results from AI tools.
• Zapier and Make – Build automations and workflows without writing code.

Customer Service Skills

• Support Driven – A community of support professionals with workshops and resources.
• LinkedIn Learning courses like “Customer Service Foundations” and “Technical Support Fundamentals.”
• Google IT Support Professional Certificate – Covers both technical and customer service skills.

Get to Know Automattic

• The Automattic Creed – Our values.
• The Happiness Engineer Blog – Stories and day-in-the-life posts from current HEs.

In this video, Job shares how a willingness to try things (and stick with them) shaped his approach to leadership, why he defines it as creating space for others to flourish, and what he looks for in the people around him. If curiosity and genuine care for customers sound like you, he’d love to hear from you.

In this video, Adrian shares what made him finally take the chance on applying, how he approaches leadership through communication and trust, and what he values most in his teammates. If you’ve ever doubted whether you belong here, this one’s for you.

If you’re reading this, you might be considering applying for a Happiness Engineer role. My name is Miguel Campal, Lead of the Retrograde, a team focused on delighting merchants who run their stores on WooCommerce. I wanted to share how I ended up here, how I lead, and what it’s like to work with me; not the glossy version, but the real one.

How I Got Here

I’ve reinvented myself more than once. Before Automattic, I lived several lives: musician, teacher, salesperson, real-estate agent, always learning, always adapting. Music taught me patience and presence. Teaching taught me how to guide without taking over. Sales taught me how to ask questions instead of assuming answers. All of that would later come into focus as leadership training I didn’t know I was getting.

I joined Automattic a little under five years ago as a Happiness Engineer. I was curious, hungry to learn, intimidated, and completely unaware of how much I would grow. Over time, I discovered that supporting people felt natural to me. I moved into a lead role three years and five months ago, with excitement but also with questions: Can I do this? Will I lead well? The answers came slowly, through relationships, one teammate at a time.

What surprised me most when I joined? How deeply Automattic trusts individuals. You don’t wait for permission here: you step forward, learn, iterate, and build something meaningful. That’s the path I walked, and the path I care about helping others walk, too.

My Leadership Philosophy

My approach to supporting team members is simple: I want people to feel safe, seen, and capable. I don’t believe in micromanaging: my job isn’t to backseat-drive, it’s to widen the road. I help teammates find the place where their curiosity, strengths, and impact meet. Sometimes that means asking hard questions. Sometimes it means slowing down. Often it means stepping aside and letting someone shine on their own terms.

When it comes to communication, I believe honesty is kindness. I try to be clear, direct, and human. English isn’t my first language, so I learned early on to speak from the heart rather than try to sound perfect. If something matters (good or difficult) I’d rather talk about it before it becomes a wave instead of after it’s already a storm. Feedback goes both ways, and I mean that literally: I learn as much from my team as they learn from me.

The way I see our work is simple: the merchant is the reason we’re here, and the team is how we get there. A great Happiness Engineer balances empathy with problem-solving, curiosity with initiative. Mistakes happen; that’s how we learn. What matters is not avoiding errors but growing through them.

Our team culture is built on trust, a bit of laughter, and shared purpose. We celebrate wins, big or small. We ask questions. We share knowledge freely. We don’t pretend we always have it together, but we always move together. My goal is for teammates to feel not only capable, but proud of how they show up.

What I Value in Teammates

There are a few qualities that stand out to me:

• Curiosity. This work rewards people who explore, who ask why instead of accepting what.
• Empathy. Merchants don’t come to us at their best. They come when something is broken. Compassion is power.
• Clear communication. This is our oxygen. It builds confidence, alignment, and trust.
• Ownership and initiative. I love watching someone pick up an idea, shape it, and run with it; not because they were asked, but because they believed it mattered.

If you see yourself in these traits, you’ll likely find yourself right at home here.

Real Talk

This job isn’t easy. You’ll need resilience, patience, and the kind of curiosity that digs deeper instead of getting frustrated. You’ll face ambiguity. You’ll make mistakes. You’ll stretch beyond your comfort zone. But you won’t do it alone. If you join my team, I’ll be in your corner, listening, challenging you, celebrating with you, and helping you find the path that fits you.

Closing

My hope is that you walk away from this feeling like you’re not applying to work for someone, but with someone. If you care about merchants, if you want to grow, if you enjoy solving problems with kindness and clarity, you might be one of us. I’d love to meet you, learn your story, and help you write your next chapter here.

If you’re thinking about applying: do it. You might surprise yourself; I certainly did.

My Journey

My story begins with completing a Digital Systems Engineering degree and not being entirely sure what to do next. I landed an internship with a tech company in Greece that actually trained interns and placed me in customer support—the beginning of an amazing journey. I couldn’t have asked for a more supportive (no pun intended), more knowledgeable team. Everyone helped me learn the work, collaborated with me on complex tickets, and joined customer calls when frustration levels rose. When the company was acquired and the culture crushed, I moved to a small company building WooCommerce plugins.

I joined Automattic in 2021 through an acquisition, already leading the support team. I was asked to keep leading during the transition, which felt scary. The previous company had just 9 people, where Automattic has over 1400—I didn’t know what to expect from such a tremendous change. After the rough first months focused on learning, it turned out I couldn’t have made a better decision.

Everyone was so welcoming and supportive: no question was stupid, and nobody was too busy to help. After 4 years, I know I’d do it again. The reason? The people. Every single person I’ve collaborated with has been amazing, smart, caring, and dedicated to putting out their best work.

My Leadership Philosophy

When it comes to communication, I believe in being present, transparent, and meeting people where they are. My team and I connect daily in Slack—we have our public channel for morning check-ins and bits of personal life, a private team channel for discussions people don’t feel comfortable having publicly, and a highlights channel for important posts. If something needs individual attention, I’ll DM or save it for our next 1:1. Most of my team works direct support much of their day, so I avoid ad hoc calls unless someone tells me that’s what works best for them.

My goal with feedback is that it must never come as a surprise.. We work with personalized quarterly goals, and everyone posts monthly progress summaries. I use this data, plus our 1:1 conversations about blockers and highlights, to write short monthly updates: what went well, what could improve (and how), and optionally what to focus on next month. For yearly reviews, I gather feedback from colleagues, write a detailed draft, and share it with the team member before I submit it. We discuss and agree on the content together—I want them to have a chance to correct me if I’m missing anything that paints a different picture. When difficult conversations come up, I approach them with kindness and curiosity first. I share what I’m observing, ask for their perspective, and then we discuss a plan for improvement. I also leave room for them to suggest what they think would be a good path forward before making suggestions of my own—for an improvement plan to work, people need to have agency and really consent to the plan.

The way I see our work is about balance: delivering a satisfying customer experience while ensuring an exceptional HE experience. Balancing these two is not easy, but it’s essential if we want the work to be sustainable, rewarding, and efficient. Mistakes, whether big or small, are learning opportunities. Recently, one of my HEs forgot to share something important with a customer. I asked them to follow up to set expectations clearly; they did it quickly, and the customer was grateful! But when the same mistake repeats, that’s a sign that we need to dig deeper together to understand why it’s happening.

Our team culture is built on friendliness, psychological safety, and autonomy. Last year at our Division Meetup in Mexico—which I couldn’t attend due to family reasons—other HEs from Woo Happiness reached out to tell me they’d run into Libra and found the team so bonded they were walking together to presentations, spending lots of time with each other, and taking care of HEs who were there without their lead. Knowing that the members of Libra are really there for each other, even when I’m not around, was incredibly rewarding.

What I Value in Team Members

Curiosity is the most important trait I look for: it’s what opens the path of endless possibilities. A curious HE asks questions not merely to solve the immediate issue, but, more importantly, to understand the merchant, their business, and how to help with their long-term success. Curiosity also drives learning: wondering how things work, how we can improve a process, or how we can grow as individuals.

I value ownership and accountability—understanding when you need to take something into your hands and see it through, or ensuring it doesn’t fall through the cracks by handing it off properly. Recently, a team member spotted patterns in our interactions that led to negative feedback, pitched fixing them as part of their goals, completed the analysis, and shared it with the team—all without anyone asking them to do it. That’s ownership in action.

Finally, collaboration and knowledge sharing help us tackle complex work without fear. In Libra, this looks like shadowing sessions, Learn-Ups, or knowledge posts. And this isn’t just tenured HEs teaching newer members—it works both ways! Fresh eyes questioning how you do things is valuable. Even if you’re still learning about a Woo extension, there’s always room to share your observations. You don’t have to be an expert to contribute.

Real Talk

One of the most challenging aspects of this work is time and task management. Everyone needs to develop a solid plan to keep up with demands while respecting their personal time—consistently working on goals, tracking tasks and deadlines, and collaborating well with colleagues.

Here’s what people might not realize: this role isn’t just about how much you know about WooCommerce or how quickly you can answer questions. It’s about being empathetic, connecting with customers, and genuinely wanting to find the best solution for them. It’s about balancing that empathy with curiosity about their site, business, and goals—taking a step back to see the bigger picture. One thing I’ve learned from all my support roles: it’s often not about answering the question that’s asked, but understanding why it was asked, and addressing the actual issue behind it.

Closing Paragraph – Join Us

I hope you take away that Libra is a team that will support you and help you grow—if you’re willing to put in the work. We openly share knowledge, answer questions, and give feedback, and we expect the same from new team members.

If you’re reading this and feeling hesitant because you don’t tick all the boxes, but this opportunity sparks your interest, you have WooCommerce experience and are curious to take it to the next level, and you’re open to receiving feedback and applying it to improve your work—I’d encourage you to take a chance. We’d love to hear from you.

More than a decade later, I still love my job in Happiness. I lead HappOps, our support operations team: we build the operational infrastructure that enables every Happiness Engineer to deliver excellent customer experiences. If you’re considering a role as a Happiness Engineer, I want you to know about how HappOps would support you and what kind of leader I try to be.

My Journey

I started at Automattic in 2014. A couple of years in, I became a team lead for 11 WordPress.com Happiness Engineers (HEs). Back then, we didn’t have an operations team. HEs and team leads filled that gap ourselves as we saw it emerge. We managed data, scheduling, workflows, tools, and staffing—while also serving customers and our teams. It was messy. It was hard work. And we learned a ton.

As 20+ team leads attempted to drive the support organization forward while also leading our teams, the operations load outgrew our capacity to manage it as a collective. We recognized that we’d benefit from individuals dedicated to operations, and we began shaping what is now HappOps: our Happiness Operations team. During that period, I took some time away from Automattic to lead operations for Support Driven, a customer support community. Eighteen months later, I brought those learnings, and a broader perspective on the support industry, back to Happiness. 

This is the beauty of a career at Automattic: you get to grow with the company. I grew into my career path by identifying gaps and doing my best to fill them. That’s still how we work today.

My Leadership Philosophy

My strength is not that I am the smartest person in the room. On the contrary, I am surrounded by people who are smarter than me. As a leader, my strength is to listen, to ask questions, and to lean into the talents of the people around me. Every day, I get to work with highly intelligent, funny, and generous people who are driven, and who genuinely want to help Happiness and Automattic succeed. My job is to create the conditions where they can do their best work.

Coming from years of collective decision-making, I’ve learned that clarity matters. I try to be direct about expectations, decisions, and reasoning. When I don’t know something, I say so. When someone on my team has a better idea, which happens regularly, I get out of their way and/or actively support them.

Our distributed culture is built on open communication and knowing that great ideas come from anywhere in the organization, not just from leaders. As a leader, I am a voracious reader of others’ processes, decisions, and goals, and I am continually looking to role models who are often not leads–to see how they do things. I love that I can learn from our Systems, Finance, HR, Engineering, Product, and Design teams through our internal network of P2s where everyone’s work is visible. When I was away from Automattic, I craved the written context that is abundant across our internal communication tools. I’ve learned so much from working here, and I’m still learning.

What I Value in Team Members

I appreciate people who are curious and resourceful, who dig into problems, ask good questions, and find paths forward even when the answer isn’t obvious. I value clear, proactive communication, especially what, why, and when. In a distributed company, this is everything. Tell me what you’re working on, what’s blocking you, what you need, and when people can expect what you’re working on to ship. I am delighted when team members underpromise and overdeliver.

I appreciate people who take ownership—not just of their tasks, but of outcomes. If something’s not working, flag it. Propose a solution. Help us get better. I love when people come to me with a problem that is paired with “This is how I’m thinking of solving it.” 

I value kindness and humor. We spend a lot of time together, and the best teams I’ve been on are the ones where people genuinely enjoy each other and what they’re doing. People who enjoy their work and their workplace tend to do great work that they’re really proud of.

Real Talk

If you become a Happiness Engineer, you’ll have HappOps in your corner. We’re the team that builds the tools, dashboards, and workflows that help you do your best work. We handle forecasting and staffing plans so your division can plan effectively. We identify and remove operational barriers so you can focus on what matters most: helping customers.

That said, working in support isn’t always easy. Some days are hard. Customers are frustrated, queues are long, and you won’t always have a clear answer. What I can tell you is that you won’t be doing it alone—HappOps exists to make excellent customer experiences possible, and that starts with supporting you.

If This Sounds Like You

I started as a Happiness Engineer over a decade ago, and I’ve grown from HE to team lead to operations leader, all within Happiness. That path exists here. You can build a meaningful, long-term career helping people.

If you’re curious, collaborative, and genuinely love helping others, I hope you’ll consider joining Happiness. You’ll be surrounded by smart, fun people who want you to succeed, and by teams like HappOps working behind the scenes to set you up for it.

Ramona, a Happiness Engineer on the Customer Growth Team within WooCommerce, takes us through a typical workday in Happiness. As part of a fully distributed company, Ramona works from her home office, connecting with WooCommerce merchants around the world.

In this video, Ramona shares what makes her role special: regular video calls with merchants to understand their businesses and support their growth. She walks us through her daily routine, from documenting merchant conversations to keep her team aligned, to collaborating on strategies that help stores increase revenue and solve technical challenges. These one-on-one conversations with merchants are what Ramona loves most about her work.

You’ll also see how Automattic’s commitment to flexible work plays out in real life, whether that means taking breaks to play with her cats or connecting with teammates through Slack channels dedicated to both hard work and fun.

Whether you’re curious about the customer-facing side of Happiness Engineering, considering applying to join our team, or simply want to see the authentic human side of what we do, Ramona’s video offers a genuine look at life on the Customer Growth Team.

Interested in learning more about the Happiness Engineer role? Check out our other blog posts or visit our Work With Us page to see current openings.

For Happiness Engineers, team meetups are an awesome perk of the job. Once or twice per year, teams head to incredible locations around the globe for five to seven days of collaboration, learning, and connection. Past meetups have taken teams to Seoul, Lisbon, New York, Tokyo, Edinburgh, and countless other cities where teammates can work together and experience new places.

Why We Meetup

Working remotely gives you incredible flexibility and autonomy. You get to choose where you live, how you structure your day, and what your workspace looks like. But face-to-face time is crucial for building the kind of relationships that make distributed work truly successful.

When you’re solving problems together in person, discussing support strategies over coffee, or sharing productivity tips between sessions, you build connections that carry you through the other 51 weeks of the year. It becomes so much easier to understand the nuance in a Slack message when you’ve explored a new city together or shared meals with your teammates.

What Happens at Meetups

Team meetups blend work and exploration. You might spend mornings discussing best support practices, advanced troubleshooting techniques, or planning your team’s quarterly goals. Afternoons could involve collaborative projects, skill-building sessions, or working your regular shift while sitting next to colleagues you usually only see through video calls.

But it’s not all work. Teams build in time to explore their host city, whether that’s visiting museums, trying local restaurants, or taking day trips to nearby attractions. The combination creates memories that strengthen team bonds and remind you why the distributed model works so well.

Work From Anywhere, Meet Up Everywhere

Team meetups show what’s possible when you embrace distributed work without losing human connection. The flexibility to work from your chosen location combined with the chance to collaborate in person creates the best of both worlds. You build a career that fits your life while forming genuine connections with colleagues across the globe.