Build #65 - Rethinking senior recruitment in an emerging AI world
Most tech founders I work with realise how important senior hiring is, but even the best of us sometimes treat it as a necessary task and not a strategic intervention.
More so, hiring is frequently done on the backdrop of urgency due to someone leaving or a new client expansion, which can further push towards speed over thoughtfulness.
Something that can be overlooked is how C-Level recruitment isn't just about finding someone competent to do what’s gone before and the security that gives; it’s about shaping the next phase of your business growth.
That used to mean looking for people with prior experience (ideally by the bucket load) who can slot in seamlessly where possible.
However, in the last year especially, AI has shifted the foundations of what work in our industry looks like and what it means to have “done it” when few have is changing faster than most hiring models and founder strategies can keep up with.
Rushing to role before strategy
Senior hiring often starts with a quick internal conversation.
“We need a COO. Someone who’s been through this stage and can help us do the same.”
And off we go. We write a role specification based on the previous incumbent and look for them in our competitors or similar companies.
But we rarely stop to ask: what kind of business are we building now in this era of increased security risks and AI escalation, and what does that really require?
Not just in skillsets, but in mindset, influence, and pace.
Why hire from those doing the same as we were, when we could hire better, smarter, and be at the forefront of the new wave.
Another common blind spot is assuming that bringing in a senior hire will resolve an area of pain or unlock a founder’s time. It’s a tempting shortcut.
But it only works if the structure around that hire is clear and ready. Otherwise, you end up with drift: unclear accountability, clashing expectations, and strategic decisions being made in isolation.
A new hire that’s now been thought through can create more problems than you started with, not to mention taking up much more time.
tl;dr a great hire can’t fix a company or organisational structure that doesn’t know what it needs.
AI is reshaping the roles we’re hiring for
One of the quiet shifts happening right now is that AI isn’t just transforming roles from the bottom up.
It’s changing what leadership looks like too.
I would say even more so, because without leadership that understands our AI-quake that’s happening, how can we be forward thinking enough to hire for this next phase of tech?
In the same way I remember print media being left behind as us New Media Kids (as we were back in the late 90s!) starting taking over.
A CTO used to need depth in engineering and architecture.
Now they need to understand how to orchestrate ethical AI-driven teams, oversee responsible data practices, and know when to build versus when to prompt.
Marketing leaders are navigating generative content, journey automation, and attribution models that update themselves.
Even COOs are increasingly managing tech-first operations where the system could be doing the decision-making instead of a human advisor.
This means we need to stop hiring based purely on what someone’s done under the old systems, and start asking how well they adapt when the landscape underneath them changes.
Curiosity, systems thinking, and the ability to build hybrid human-machine teams are fast becoming non-negotiable traits in top-level hires - yet something I’m not seeing play out as fast as I would have expected in our web tech industry.
A lot of companies are about to be left behind, and they’ve not even realised yet.
Structure before search
Before you even start briefing recruiters or activating your network, it’s worth doing the hard thinking: what shape does this hire need to take not just in role but in resilience and fast adaptability, and how do they fit into the company in a way that is successful in both the current and new era of tech operations and offerings?
That doesn’t (just) mean drafting a job spec with 14 bullet points.
It means understanding your business model at this stage and what you’re optimising for next.
It means having trusted advisors to point out your blindspots and consider your own skills gap analysis ready to make sure you’re hiring for the future, not the past.
It means working out who’s already in your company keeping an eye on trends and able to adapt, and how your teams are structured to give your leadership the best chance of success as we all navigate what’s coming next.
Final thought: Your next hire is part of your AI strategy
We are at the start of a shift where AI isn't just a tool but a second operating layer for the business. It affects how decisions are made, who makes them, and how fast they flow.
This flip will - like print vs new media - decide who the forerunners are in our next wave of tech, and who gets left behind.
This has huge implications for your organisational design.
You may need fewer managers and more systems thinkers. You might hire engineers who focus not on writing code but on validating, securing, and optimising what AI writes for them.
You’ll likely need new governance roles to manage data risks and internal AI use, especially as more of your operations become automated by default.
Security also takes on a different shape.
It’s not just about firewalls and access control any more. It’s about tracking how AI agents interact with your business logic and where unintended outcomes can emerge.
So when you’re hiring at the top, don’t just ask “can they lead this function?”
Ask “can they help us lead in this new context?”
Thayer's recommended reading on this topic: