Sep 28, 2026 · 43 min · 11 segments
Anna Kelk has spent her whole career inside rocket ships. She started out at Ask.com (the Ask Jeeves search engine) back in 2001, helped scale A Cloud Guru from around $20 million to $140 million ARR…
So as they were growing so quickly, it must have felt that the product was breaking at times as well.
When you get to that point, like how do you prioritize what to focus on next? And, you know, how do you kind of build that next level of scale into the product operation?
I think in terms of prioritisation, you have to be really clear about what the company level priorities are and be really rigorous about only prioritising things which are going to ladder up to that result.
You've also got to, for companies, for expansion and scale, you've also got to make sure that you're investing in platforms and systems and the foundations which will get you to the next stage as well.
Sometimes it's hard to know when to push the button on that, particularly if you're taking people away from building, you know, the more tangible stuff.
like the product that you ship, saying, okay, I'm going to take one third of those people away to build out infrastructure is it can be a really hard sell.
So I think what you need is some good storytelling abilities and able to sort of reflect on companies who have done that really well and why and and perhaps companies who didn't scale well and why.
And generally one of the whys is because they didn't invest in those foundations soon
Yeah, I think biting off more than you can chew in the sense that, you know, perhaps you are – You've scaled to one region.
You've got some customers there, but you haven't really nailed it there, but you're already thinking about, okay, now we're going to do this one.
So what I've seen go wrong there is that you're already investing in something new before you've achieved product market fit in a region where...
So just understanding some of your limitations and making sure that you're applying rigour to some of those limitations.
decisions around, okay, if we scale out to this new region, what does it actually mean for the one that we've just rolled out to where we haven't really achieved product market fit? The result could be that actually we have two regions now where we don't achieve product market fit, which is a really poor outcome.
And, you know, you get one chance to do a successful launch and build that momentum.
So as they were growing so quickly, it must have felt that the product was breaking at times as well.
When you get to that point, like how do you prioritize what to focus on next? And, you know, how do you kind of build that next level of scale into the product operation?
I think in terms of prioritisation, you have to be really clear about what the company level priorities are and be really rigorous about only prioritising things which are going to ladder up to that result.
You've also got to, for companies, for expansion and scale, you've also got to make sure that you're investing in platforms and systems and the foundations which will get you to the next stage as well.
Sometimes it's hard to know when to push the button on that, particularly if you're taking people away from building, you know, the more tangible stuff.
like the product that you ship, saying, okay, I'm going to take one third of those people away to build out infrastructure is it can be a really hard sell.
So I think what you need is some good storytelling abilities and able to sort of reflect on companies who have done that really well and why and and perhaps companies who didn't scale well and why.
And generally one of the whys is because they didn't invest in those foundations soon
Yeah, I think biting off more than you can chew in the sense that, you know, perhaps you are – You've scaled to one region.
You've got some customers there, but you haven't really nailed it there, but you're already thinking about, okay, now we're going to do this one.
So what I've seen go wrong there is that you're already investing in something new before you've achieved product market fit in a region where...
So just understanding some of your limitations and making sure that you're applying rigour to some of those limitations.
decisions around, okay, if we scale out to this new region, what does it actually mean for the one that we've just rolled out to where we haven't really achieved product market fit? The result could be that actually we have two regions now where we don't achieve product market fit, which is a really poor outcome.
And, you know, you get one chance to do a successful launch and build that momentum.
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