I am a born helper. When I first heard the job title “Happiness Engineer,” I thought, “What an amazing job title! I want to do that!” At the time, I had been blogging regularly on WordPress.com for about two years, and had just finished volunteering to host a community blogging challenge in collaboration with Automattic’s editorial team. They sent me a thank-you tee-shirt that said “Happiness Engineer” on it, and my life was forever changed. I pursued the role, and the first time I wore the shirt as an official Happiness Engineer was one of the proudest days of my life.

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.