Journal of Olly Headey. Co-founder & CTO at FreeAgent.

Salary Roulette

September 14th, 2021
Job ads which feature salary bands have been shown to be more inclusive and result in a larger number of applicants. Salary transparency is a staff motivator and increases engagement, so why are most companies still keeping rates secret?

HEY vs Fastmail: One year on

May 22nd, 2021

For all the social media, messaging, and productivity apps I have installed, my digital communication is still dominated by email. Sure I use WhatsApp, iMessage, Slack, Basecamp, Twitter, Instagram… but email is the constant that I can’t do without, at work or at home.

I’ve been using Fastmail for around 7 years, and before that I used Gmail. When HEY launched just over a year ago I signed up as soon as I could. Not because Fastmail had flaws, but because I quite like new shiny things, I love Ruby on Rails, and I’m intrigued by the products that Basecamp create. I don’t think Basecamp have the slickest products on the market by any means (they really don’t), but they create a narrative around their products and I found the promotion around HEY quite compelling.

I’ve used HEY for almost a year now, so it feels like the right time to reflect on the product. I should admit that I haven’t use HEY exclusively over this time. I did try forwarding all my email into it for a few weeks, but I found it something of a trial by fire and I quickly reverted. Instead I started to move different cohorts of email over to it (newsletters, GitHub notifications, receipts), enough to give me a solid experience of it without committing full time.

I wrote a popular post last year that has had thousands of views, and I think all those first impressions still stand today. What follows is a breakdown of what works for me with HEY, what doesn’t, and why I’ve ultimately decided it’s not for me.

Boosting the signal

March 9th, 2021
I had a day "out of the office" yesterday (not to be confused with the previous 360 consecutive days out of the physical office since March 13, 2020). I just had a day off, which shouldn't be a particularly big deal. If anything urgent happened I would have received a phone call, otherwise I should easily be able to catch up with things on my return. I filter my email so it's a pleasant place these days, even after a few days without checking. Slack, on the other hand, is a complete disaster zone.

A reminder that the days are long but the decades are short

February 15th, 2021
I seem to happen upon this blog post from Sam Altman every year or so and it always resonates with me. 36 thoughts on life from a 30-year-old (at the time) who appears wise beyond his years. Reading it is life detox. So go ahead and cleanse.

How I implemented custom domain support with automatic TLS certs for my SaaS app

February 14th, 2021
Managing hosting and TLS certificates for customer-specified domains can be a challenge. In this article I explain how I solved this, with relative ease, for

Update 8 Oct 2021: Include instructions for simpler Caddy install

When I first started working on Blogline (a fast, minimalist blogging platform), I had only planned to use it for my own blogs. Like most app developers (certainly those using Rails), I originally hosted it on Heroku, which has decent support for TLS if you're working with only a handful of known domains. Once I'd finished the early prototype, I decided it might be fun to turn it into a SaaS product that would allow customers to create a blog on their own domain in seconds. This didn't sound complicated technically – the main problem was how to manage TLS certificates.

📪 Free your Gmail Inbox

January 8th, 2021

Your inbox is probably a noisy place that you don't enjoy visiting. Am I right? I recently read the following tweet which motivated me to clear out my work inbox for 2021 (I only use Gmail for work).

You can do the same thing in Fastmail, Yahoo or whatever, but here’s how I did it in Gmail. If you’re using HEY this entire post is probably irrelevant! 

Music in 2020

December 28th, 2020
I thought about writing a “2020 in Review” article that was just a blank page, but rather than being facetious I thought I'd write about some of the music I listened to instead.

The problem with acronyms

December 10th, 2020
Reducing the use of unnecessary acronyms in your business will increase productivity and employee happiness, and reduce cynicism as you grow. Here's how.

Confusing vernacular isn’t a new thing to me, but I’ve noticed that an acronym[1] population steadily increases as projects, or entire companies, expand. I can sort of understand. When a company is bigger, there are more people and more things going on. More projects, more meetings, more presentations. Typing “Engaged User Growth Hack” becomes tedious the 14th time you write it in your proposal, so someone initialises it (EUGH) the first time and uses the acronym there on in. Once the document is circulated, it’s inevitable that at some point – it might take a few meetings, but eventually – it becomes common parlance. "How is the EUGH rate looking this week, Ted?"

One of the many problems you’re going to encounter in a growing business is a lack of clarity among staff. A successful business is one where employees understand things, and when they don’t it's okay because they know where to go to find the information required to understand things. 

Whether you’re a new hire reviewing an onboarding guide on your first day, or a seasoned employee reading the latest project proposal, you’re probably going to be faced with a sea of acronyms. The more there are, the more confused you'll be. This is bad for morale and bad for business, so it's your job as a leader in an organisation to spare everyone from this misery by eliminating acronyms as much as possible in your organisation. Here are my top tips.

The Ascension

November 26th, 2020

Despite liking the idea of liking Sufjan Stevens, the reality of listening to one of his albums has never lived up to expectations for me. I felt the same way about Nick Drake, Bright Eyes and countless other well regarded singer-songwriters. The Ascension is different.

I sort of always have been but I'm really in the mood for spaced-out dreamgaze right now. Coronavirus continues to circulate and dominate our lives, autumn broods outside while we hunker, locked down, inside our houses. As with American Head, and to some extent Folklore, the soft keys and subdued mood of The Ascension fits 2020 perfectly for me.

👋 Farewell, CodeClan

October 29th, 2020
Around five and a half years ago I was asked by Polly if I would join a supervisory group who were tasked with understanding the feasibility of creating a digital skills academy for the software industry in Scotland. The idea was that this academy would train workers in software development over a 16 week course, then help them find jobs within the industry. The ultimate goal of this initiative was to help to bridge the increasing digital skills gap we were seeing in Scotland. Understandably, there were people who thought this couldn’t be done. Two of the biggest concerns were that the revenue model would never work and, perhaps more worryingly, that it wasn't possible to teach someone to code from scratch in 16 weeks. We went ahead and did it anyway.

After a lot of hard work (not on my part really!) the academy became a reality in June 2015 with the official announcement of CodeClan as "the UK’s first dedicated accredited software skills academy". The first cohort of students started in September 2015!

As with all startup businesses, the journey has been a rollercoaster of highs as well as lows. Some of the hard times were particularly pronounced since CodeClan is a social enterprise and the course was being offered at less than cost (the difference being made up by the partner programme). Yet, despite these challenges, the company has not only survived, it has thrived and forged ahead even in the face of the most difficult business challenge of modern times – a global pandemic.

CodeClan is now operating across three sites (Edinburgh, Glasgow, Highlands & Islands) and they recently celebrated 1,000 graduates which is an incredible milestone. At FreeAgent we have hired six CodeClan graduates over the years, all of who are amazing (and are all still with us).

It's a remarkable achievement.

Five years on, it's time for me to step down from the CodeClan board. I've thoroughly enjoyed being a board member, it has been a brilliant, rewarding journey – a privilege, really – and I've learned a huge amount from the experience, from my board colleagues as well as Polly (CodeClan Chair), Melinda (CEO) and her excellent team.

Thank you to everyone for letting me be part of it all and I look forward to seeing where CodeClan goes next!  👋