A little over a year ago, I took on a new role at Automattic: leading the Happiness Experience (HappEx) team. This team is responsible for overseeing the Happiness experience from before someone applies to Automattic, through their last day as a Happiness Engineer. We started out roughly divided into two halves: Happiness Experience and Happiness Hiring. Over time, we’ve grown a bit to include Happiness Onboarding, Leadership Development, and we’re moving with purpose towards Happiness Growth.

This role is very fulfilling for me. I have learned absolute mountains about hiring for this role that I’ve lead for a long time (Happiness Engineer), and I’ve taken a lot of agency to work with my team’s stakeholders to be proactive about improving the Happiness experience at a fundamental level. Fortunately, everyone at Automattic, including my main “external” partner in this work (the lead of the Happiness organization, Andrew Spittle), has the exact same goals. We may have slightly different interpretations and theories about how to move forward successfully, but starting on the same page is a wonderful advantage, and makes work truly energizing and fun every day. Additionally, my team balances taking our work to heart with a healthy dose of whimsy. We hold each other accountable, we deliver when we say we will, and we communicate clearly, kindly, and consistently.

Hiring and Onboarding

Soon after moving into this role, we were mandated to hire at least 25 new HEs as ASAP as possible. We managed to hire 33 new HEs before the end of the year (some started in 2021). Late in 2020, we also recognized that if we were going to keep going at the pace we were, we were going to make some changes. We didn’t want to maintain the pace we had been going at, either, but actually increase it. We wanted to hire nearly seven times as many Happiness Engineers in 2021 as in 2020. That meant a radical change in nearly everything we do. We decided to tear our entire process apart and rebuild it from the ground up. We did this in tandem with running our old process, so we didn’t lose any time.

In November 2020, we identified that the biggest thing we needed to change was the length of our (paid) trial. The old trial was four to five weeks long. During that time, candidates would get hastily trained in all aspects of being an HE, then perform the work. We’d give feedback, they’d have a trial buddy and a trial lead, and we’d just see how it went. We decided to cut it to a three week trial, max. We also changed what we look for in the trial, and how we introduce people to the work. The trial is designed specifically to have two key components: the candidate gets to try out the work and decide if it’s right for them; we get to evaluate the candidate’s skillset. Keeping that in mind, we changed the trial to be much more strictly segmented. Week one involves some broad training about being a Happiness Engineer at Automattic, then some shadowing sessions, and a chance to ask plenty of questions. Week two involves some specific training in tickets, some paired ticket time, some solo ticketing, and a troubleshooting project. Week three includes specific training in chat, some paired chat time, and solo live chat with customers. Another key decision we made was to structure the trial so it would be part-time for everyone. We used to allow folks to take their 5-week trial full-time or part-time. Obviously, that ended up giving people who could invest all their time into the trial an advantage. So by reducing the trial to fewer than 20 hours a week, and gating each week very specifically, everyone has the same opportunity for input and output. Particularly in COVID-times, we were very concerned about how to make the trial as equitable as we could for people who may be teaching their kids all day at home, or caring for a sick family member, or who may just be stressed out of their mind. Reducing the time input and being super clear about our expectations upfront (both in terms of input and output) means that candidates can more easily decide if moving forward with a trial is right for them.

By February 2021, we were ready to launch our new program. So we did. We went through constant iteration on our pipeline process, and indeed, we still are tweaking and iterating our application questions to help us best ask for the exact things we want candidates to show us. We also brought onto the team an Onboarding Lead to build a formal onboarding program for new HEs that was universal. Previously, our onboarding was homespun, developed by the different divisions (WooCommerce Happiness onboarding was different from WP.com Happiness onboarding, for example). We also developed an understanding of how to handle onboarding for our smaller divisions (Tumblr Happiness and Trust & Safety, for example), and how to allow for necessary organic development of style and sense of community between the divisions, without actually leading to vastly different experiences.

We decided to start with the broadest possible onboarding, and narrow from there. Today, new HEs are onboarded into Automattic, then Happiness, then their division and team. They are invited onto their team from day one, so they know where they’ll be working, and who their lead is and their team mates, but we want them to feel at home as Automatticians first. Before the end of March 2021, our first new HE started in our new Happiness Onboarding (HappOn) program. We created a team to work exclusively on onboarding, with these folks responsible for staying very close to the work in their own division, and making sure that the onboarding for each division aligns where it makes sense to, and also helps folks set up for success as early as possible in their new team. To date we’ve graduated around 30 Happiness Engineers from onboarding, and have nearly 40 in the program (or starting soon).

Leadership Development

Something that Happiness has been invested in for a long time is leadership cultivation. This is a program that I helped to run for a few years when I was a lead-of-leads (LOL) in Happiness itself (through a curiosity of org charts, I no longer am technically in the Happiness organization; I’m in Talent, though my heart firmly resides in Happiness). Leadership cultivation is a program that helps folks who are unfamiliar with leading at Automattic how to be successful in the role, and what to expect. We like to say that if someone goes through leadership cultivation (a several months investment) and decides that they don’t want to be a lead, that is a good result! They will have gained new skills, new perspective, and they’re not in a role they don’t actually want to be in. Our intention with leadership cultivation is primarily to build our bench of available leads within Happiness. This intention is primary because it’s the most pressing. We are constantly filling leadership roles, both permanently and temporarily, so maintaining a bench of folks across all regions who are well trained and feel confident about leadership is vital to Happiness. Our secondary intention (which is not less important, but is necessarily less urgent) is to afford new skills across Happiness around leadership. Everyone can benefit from leadership training! Lead cultivation, however, is incredibly time intensive — which of course is a main benefit of it. Clear, direct attention from a tenured lead who coaches the candidate through the process, helps them develop their instincts around leadership, and gives them tools/resources to work through the rest. We ran lead cultivation in a one-to-one manner for years, and it worked okay.

Late in 2020, we recognized that if we were going to hire so many more Happiness Engineers, we were going to need to figure out a new way to run lead cultivation so it was one-to-many. In January, we launched leadership cultivation cohorts. To date, we have 14 graduates, 20 people in cohorts, and a similar amount interested in starting. Our leadership development program also includes support during leadership tenure. We call these leadership dens, and each den comprises 5-7 leads across Happiness with a mix of tenure and experience. Our (HappEx) role in dens is to facilitate; really, leads help each other more than anything. This gives them a safe space to provide support, ask for help, and psychologically come to the realization that they’re not alone in this work.

Given the popularity (and importance) of these programs, we just recently brought on a second person to work on leadership development full-time!

Growth and Development

Training for Happiness Engineers has always been a homegrown affair. We create the training we wish we had had, and stash it in the field guide (the handbook for all Automatticians). With nearly 400 Happiness Engineers alone, we have far outgrown this haphazard arrangement. And to be fair, Happiness Engineers themselves have worked hard to keep relevant information readily available for their peers. We have a training guild who has worked tirelessly at this, and various subject-matter guilds (i.e., domains guild, account recovery guild, CSS guild) that build and maintain their own training. And that all works okay for the work right in front of you (and sometimes not, when things get outdated). But what about actual career growth? What about building a sense of accomplishment and ownership within the Happiness role over the course of a decade? For a long time, the “growth path” in Happiness was assumed to be “go into leadership.” At Automattic, we don’t give pay raises for leadership role changes. Compensation is tied directly to impact, so pay may follow, but it’s not a guarantee. Leadership definitely isn’t for everyone, and the opportunity to move back out of leadership without financial penalty is crucial. For awhile, folks began to assume that “growth” in Happiness meant becoming a developer (and for some people, that’s true! It’s a great next step for some of our HEs). But that’s again not right for everyone, and our internal Developer Apprenticeship program is a big time investment (rightly so). So we have a gap between the time when an HE leaves onboarding and gains proficiency in the role (we feel this should take one to two years), and the next phase of their career. It’s possible to do rotations to different divisions (from WP.com to Tumblr, for example), and that is absolutely career development, but we don’t have structured training with consistent evaluation and gating criteria. So we don’t have an ideal gauge of what all our Happiness Engineers know, today. Happiness, as an organization, works and it works pretty well. But “pretty well” is not good enough. We can do so much better, and serve Happiness Engineers far better with career growth and development. This is something we’re working on now. We’re currently hiring for an instructional designer to begin to get our arms properly around this work, and then we’ll build this team out to serve Happiness effectively for the next several years.

Future Happiness

Today is a great day to look at whether you’d be a good fit for Automattic. Maybe we’ll see you in Happiness soon!