Just over fifteen years ago I shared about joining Automattic and today is the fifteenth anniversary of my start date and has me in a reflective mood. The past fifteen years have seen alot of change both personal and professional and this post is only going to contain some of the highlights.
Over the past fifteen years at Automattic I have had a lot of different roles, so many that it is hard to imagine it has only been fifteen years. When joining calls with new co-workers or external partners it is always hard to work out how much detail to share and what is or isn’t relevant to the discussion at hand but here I am going to try and list out everything. I am sure there will be things I don’t remember!
- Happiness Gardening – I spent the first ~4 1/2 years supporting our incredible support teams (and growing a team to do that work with me). This included everything from iterating on internal and external tools to deep debugging of end-user issues with WordPress.com sites. Along the way I picked up a background interesting in Trust and Safety tooling and automation that set me up well for my current role.
- Big Data – I spent the next ~3 years working in the “Big Data” space – my job title at the time was “Space Filing Curve” – These three years saw a lot of work in the spam detection automation space, working on hadoop infrastructure as well as prototyping on user facing stats features for WooCommerce stores.
- Feeds – This was a short transitional phase where I was working on the WordPress.com reader resolving scaling issues to reduce the maintenance burden.
- Infrastructure – I spent the next ~1 1/2 years working on the infrastructure that underpins wp.cloud. It was a fun time working on scaling server infrastructure, building anti-abuse detection and mitigation systems as well as migrating 1000’s of sites between platforms with no downtime or end-user visibility.
- Trust and Safety – The past ~5 years have been spent deep in the Trust and Safety space working on Tooling, Operations, Product, and Classification systems to scale our work and make it more sustainable. This also includes venturing more into the Product space leading Akismet which is an exciting change of pace.
One thing that probably isn’t as obvious when looking at this is the fact that realistically the past 15 years have always had a Trust and Safety flavor. A lot of that time was spent working in the Trust and Safety space before it was really a recognised role inventing how things should be done as we grew.
To end this reflection – I am really proud of everything I’ve done over the past 15 years and I’ve learnt a lot and I look forward to sharing more in the coming months.

