Progression update: early vs late

A quick one about the A12

I was planning on writing about social audio and Clubhouse this week.

Unfortunately I got stuck for two hours on the A12 to Chelmsford on my way to illicitly wave from afar at some friends who’ve just had a baby. A good lesson in not relying on a specific window of time to get your writing done.

So instead I’m sending a quick Tuesday morning update on Progression stuff. I thought you might like to know what we’re up to.

A lot of what I’m focused on is timing at the moment. I have a good sense of what we need to do, but making sure we time each part right is critical. We can’t get stuck on our proverbial A12 just as we need to reach our destination.

I also have a request: that you hit reply and give me feedback or just say hello! I’d love to know what you’d like me to write about (more learning-to-be-a-CEO things? fewer ‘pound-shop Ben Thompson’ tech opinions?). I’ll read and reply to everything.


A few updates on Progression and my CEO journey right now

  • In case you missed it (completely understandable as we haven’t told anyone yet), we closed a seed round last year. That has shifted Progression from a hand-to-mouth bootstrapped SaaS into a company that can meaningfully go after a market and invest in the bigger bet we wanted to make. We’re thrilled with the folks on our cap table, the increased ability to move and the support we’re getting.

  • We’re growing healthily and bringing on some wicked customers. Woo!

  • As a result our first two full time hires (Sam, an engineer and Anna, a PM) start next week! We’ll then have a team of 8 on our Slack in total — given in November it was still just Neil and I it feels like a whole different vibe.

  • Partly because of this, I’m really trying to be more predictable and plan work better. We have quarterly goals, a north star metric and we’re running lots of qualitative product experiments and user research. The old muscles of building product as a team are starting to return…

  • However, more and more I’m realising I need to step away from being in the weeds and work ‘on the business, not in the business’. My friend Toby, CEO of Lingumi, wrote yet another brilliant piece of reflection which — though they’re a few steps ahead of us on the journey — illustrated the path I’m going to have to go down, moving from ‘how’ to ‘what’ and ultimately to ‘why’.

  • In short, this year has honestly felt like a breath of fresh air so far. We’re doing really good product work, we have focus over direction and I’m personally being pulled in fewer directions.

  • However, having a war chest introduces the option to spend money to move faster. That’s the big question for me — what do we accelerate now (we have momentum, it needs to get done regardless, so sooner is better) vs wait on (we don’t know enough or some other part of the puzzle isn’t ready).

  • This year, for me, is about being able to stop blocking everyday product work and carve out time to make really important decisions on the above, plus work on other strategic things (product direction and positioning, partnerships, go to market etc.).

  • As part of my focus on removing myself from everyday product work, we’re looking for a senior product designer! If you know of anyone great, please do introduce us.

I’m really looking forward to keeping you folks updated as I more from founder to CEO and learn how to be a better CEO as we grow. Again, if there’s anything from above that you’d like me to dig more into, I’d love to hear from you.


Hopefully this week’s newsletter will be (a) on time and (b) a bit less rushed. For now though, thanks for reading and I wish you jolly good health in your various versions of lockdown, working from home and snowy/Covid times.

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