Meet Anna Holland-Smith, Developer At Automattic

Anna Holland-Smith


We recently caught up with Anna Holland-Smith, Internal Developer Advocate at Automattic. It was great to catch up with Anna in this Q&A and find out about her tech career so far, her top tips and advice as a woman in tech.

Former criminal defence lawyer, turned Developer Anna Holland-Smith now find herself in the role of Internal Developer Advocate and Head of Engineer Development, at Automattic. In this thoroughly motivating Q&A, Anna shows that you can indeed transition into tech at any stage of your life and career.

What made you change your career path from lawyer to Software Engineer?

There are many factors that contributed to my decision to leave law. Whilst I was dissatisfied with the pressures and the unsustainable workload of criminal law, there were aspects of the role that I deeply enjoyed. The decision to leave behind any career is never an easy one and for me it was one that took a great deal of consideration and a strong dose of self-belief. I was early in my legal career and I definitely felt pressure from myself and others to stay put. Many of my peers and colleagues held traditional views on what a “career” should look like and career changes were perceived as something to be discouraged.  The catalyst for the change came when I started learning to code. I wrote my first line of code through CodeFirst:Girls. Through the course I was exposed to the variety of roles that are available within the tech industry and my own pre-conceptions of the industry were challenged. By the end of the course, I had fallen in love with coding and had grown increasingly intrigued by the idea of becoming a software engineer, a career that I had previously mistakenly believed was not available to me. 

Birds eye view of a Macbook with mouse and keyboard

Which route did you decide to go down in order to transition into a tech role?

Eventually I decided to accelerate the process of a career transition by joining an intensive coding bootcamp (Makers Academy). This was back when this particular route to entry was less well established in the UK. The course itself was 16 weeks long (with 12 weeks of this taking place in-person). It was, of course, an incredibly intense approach to learning and I recognise that this approach to learning isn’t suitable for everyone and the opportunity to commit time and sacrifice income in order to do this, is not something available to everyone.  I completed the course and started my first role as a Software Engineer at the BBC less than a month later. This was the first and only job I had applied for. This is not necessarily a representative experience and I have observed how the Junior Developer market has become increasingly competitive in more recent years. 

Have you always had an interest in tech or did it crop up later in life?

For me, the interest in tech definitely came later in life. Unusually for someone of my generation I grew up in a house without a television and I didn’t get my own computer until I went to University. Technology wasn’t something I’d interacted with or been intrigued by and it certainly wasn’t a career path that I had been encouraged to follow.  

What’s your advice for women considering making that career change? 

Two female colleagues looking at a laptop at a desk

It’s not a decision to be taken lightly, and there are lots of paths you can take, which can feel overwhelming. Knowing where to start can be difficult. Fortunately there are now plenty of organisations and individuals who are doing incredible work to destigmatise career changes and to provide support, educational resources and encouragement for anyone who is trying to pursue this.

I’d advise anyone considering a career change to invest in building up and leaning into their networks. Whether it’s online or in-person, surrounding yourself with others who are working towards the same goal (or who have done so previously) is both rewarding and incredibly motivating. 

Interestingly, it’s through connections I’ve met through my work and interests in tech that I’ve found every role I have had in this industry. I applied for my first engineering role at the BBC after seeing one of their Engineers speak at an event. I spoke to him afterwards to learn more about the role and the culture of the organisation, and he was able to refer me for a position. My second role in tech came about when I was headhunted for a position after someone in my wider network had put forward my name. I came across my most recent role when a connection of mine Tweeted about the opportunity. Beyond the obvious impact it has had on my career, investing in building relationships in and around the industry has afforded me some incredible insights and opportunities to benefit from mentorship and sponsorship of others at every stage of my career. It’s also opened my eyes to roles and specialisms within tech that I hadn’t known to exist. 

What do you enjoy most about working at Automattic?  

I think most people will say that the best thing about Automattic is the people. We might be a distributed company, but that’s not to say we aren’t a social bunch! 

What does the role of “Internal Developer Advocate” involve?

In this role I work at the intersection of my interests, focussing specifically on the people side of technology and prioritising and promoting the developer experience. Currently this sees me overseeing changes to how we onboard our developers, support and encourage our developers into leadership roles, and encourage professional growth and internal mobility across the engineering organisation. 

Automattic employees

How would you describe Automattic’s culture?  

Automattic’s unique and distributed working culture is one that has been written about extensively. I remember preparing for my current role by reading The Year Without Pants and consuming any and all blogs I could find on the subject (naturally and helpfully, as the company behind WordPress.com and Tumblr, Automatticians are prolific bloggers).

I was particularly intrigued about what it would be like to work at a company that had moved away from the use of email for internal communication and embraced transparency and asynchronicity in their work. I could see how this model of working could make for a more equitable, inclusive, and democratic culture of work. Without the need for an office or a daily commute and with the freedom to hire globally, Automattic is a company that can redistribute opportunity.

A quote favoured by Automatticians when describing the importance of this approach is that whilst “talent is evenly distributed, opportunity is not”. Automattic’s culture and approach to hiring subverts this very idea: we are now 1301 Automatticians, located across 77 countries.

What are your favourite online resources for developing your coding/tech skills?   (I.e. blogs, websites,games, courses, etc) 

I enjoy learning by doing, so I tend to favour resources that encourage an interactive element. Since I don’t code as part of my job any more, I continue to exercise my skills here through coding kata and racking up points on CodeWars and I have a number of pet projects I am always working on for fun.

For other content – I’ve always followed the blogs and talks delivered through the Dev community and Code Newbie to be particularly useful for early career developers. Now that I find myself working as a Lead and closely with Engineering Leads, I get a lot from the content delivered by Lead Devmany of their talks are online and I can pick any one of them and learn something new!

How do you think we can get more women into tech?

I’ve thought a lot about this over the years and the truth of it is there is a lot to be done to encourage women into tech, and even more to be done to keep them there. To address the pipeline problem without addressing the retention problem (women are leaving the tech industry at a disproportionate rate) is to impede any progress towards parity. 

We can begin to address both of these through increasing the visibility of women in tech roles. By this, I don’t mean that they need to be paraded out for diversity events, but that they should be represented (and visible) within your workforce and within the industry at large, they should be speaking at your conference, represented in the boardroom and on interviewing panels.  When this type of visibility is present, you start to see it in your hiring pipeline.

How does Automattic currently promote diversity and inclusion?

We cannot claim to be perfect, but we do place diversity, inclusion, and belonging at the centre of our culture, and we are open to learning in public as we seek to improve. 

To support, deepen, and expand Automattic’s Diversity and Inclusion efforts, various Employee Resource Groups (ERGs) have come to life thanks to efforts from passionate Automatticians. An ERG is a group of Automatticians that identify with each other through a shared characteristic or life experience — examples include (but are certainly not limited to) race, gender, age, sexual orientation, parenthood, and veteran status. ERGs are communities where colleagues connect with and support each other and work together toward common goals.

What’s the best piece of career advice you’ve ever received?

I’m not sure whether it’s some advice I’ve ever received, but it’s a realisation I’ve had tha
t I’ve found to be incredibly useful. Once I realised that not all career progression is or should be linear, I became less intent on ticking the boxes that would allow me to transition from Junior, to mid-level developer, and from mid-level to senior, and so on, and became more motivated to explore and follow my own specific interests. Once I started to do this, I discovered and was offered career opportunities that I hadn’t previously known to exist and that better reflected my own skills and interest. Following a non-traditional career path has allowed me to carve out my own trajectory in a field that is constantly changing and evolving. 

Anna says “Having successfully transitioned into a new career in tech, I am committed to democratising coding education and promoting a more diverse, inclusive and equitable tech workforce. Working at one of the earliest and largest fully-remote/distributed companies, I’m also particularly interested in exploring the future of work and promoting the benefits of remote and flexible working”

Neon sign reading 'Do Something Great'


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