Careering into AI
Career opportunities for the truly ambitious are emerging
We’re going to struggle not to make this a long essay, but here goes nothing.
Okay, so this issue of No Rocket Ships is special, and we make no apologies for the fact that this is about building a career using AI to power your progress. We’ve put it here on substack so that you can share more easily, and maybe even have a discussion about it. Let us know your thoughts… after all I’ve had a career as a business owner rather than an employee - I may have got this all wrong.
Why now?
We’ve seen enough progress within mid-sized and large organisations to have a clear view of where the opportunity lies, and who should be going after it.
The scale of this change is 100X what’s gone before. Every part of every business will have some AI in a few years time, and the understanding is incredibly low currently. In most large enterprises there are execs with 3-4 years under their belts, but they’ve covered very little ground (due mostly to the org structure and the politics).
In mid-sized companies with a small dev team - the pace is rapid. Unfettered by big politics and always constrained for resource, these guys have taken Claude in the last 12 months and accelerated away. They’ve mitigated risk with the CISO, brought new outcomes to the board, and now have permission to go harder :)
What am I arguing in favour of?
A new version of the old chief digital officer role is up for grabs, and taking the opportunity right now are mid-career technology leads. Domain knowledge plus experience is the superpower of the next few years, and if you can truly add critical thinking to this despite being a long-term employee you’ll write your own salary cheque.
Technical strategic thinkers have been constrained by subservient IT roles, but now engineering an architecture isn’t the constraint. Those often quiet and more thoughtful people finally have the tools to illustrate what they’ve always been good at, but unable to rally people around.
The gap is becoming really obvious to most of us - progress is being made, but the speed of change is a competitive advantage, and both control (in all forms) and choice (use cases) are critical.
What allows us to claim this?
We moderate a group of senior executives in their mid-careers, I would say, and the reason we have a viewpoint here is that we are starting to see how those individuals are grasping at the opportunities that AI is giving them in order to create a new career path for themselves. It’s that that we wanted to explore here.
As our own community of Commerce Futures leaders debate AI almost weekly, a persona has emerged which vendors should consider carefully.
Mid-career, ambitious and technical, but also carrying domain expertise (they really understand the business). These individuals are finding ways to fund Claude-coded solutions to problems the business hadn’t considered. A few examples:
Automated board papers (avoiding bias)
Early submitted trading data with insights (stealing 2 days from every week)
BI, BI and more BI
Building your own stripped out CRM maybe?
Tooling to prioritise store repair suppliers based upon urgency/quality/spend
How do you get it?
This - it turns out - is the tricky part. It is not enough to just wave and say “I can help”. The politics from owners, CFO’s, resistors in general is real… and you do not want to get fired.
Here’s a picture of “Gordon” from a Persona deck I did years ago, the grumpy 55yr old CTO who never wanted “cloud” in the first fucking place :) - We all know Gordon.
Gordon is just one of the problems, but the biggest barrier is also the greatest opportunity - Nobody else has a clue!
So, what we are seeing work is as follows:
Choose something that’ll get you noticed and build it. Choose wisely. Not mission critical but something nobody can ignore (list above has worked).
Build it in your own time, using work tokens.
Show up with it to an important meeting and present - cleary articulate what it solves and how you speed things up. DO NOT MENTION GETTING RID OF STAFF.
Then do it again… and again… make sure you have three really good ideas that you can build cheaply and quickly to demonstrate value.
We’ve seen that these initial builds get attention, and either the CEO or CFO starts referencing them, or colleagues ask for help, and then momentum builds.
Do not ask for permission - we’re hearing some companies have started adoption and then become scared and locked it all down.
Also - be ready for some tough questions about cost and hallucination, find your CISO and have a quiet word once the first demo has been done. Be prepared to work harder than you have without reward for a while.
Then ask for a new job.
Not
Head of AI
Chief intelligence Officer
Brainy git
….nothing with ego….
Instead
Head of Automation
AI Operations Lead
All the best - what do we all think?




