"Up until recently I was on a clear leadership track and have experience managing large teams. But since leaving my last role I’m finding it hard to obtain a leadership role that matches my experience level, and the people management aspect doesn’t seem to be translating in the current job market. What should I change about my approach?"
Navigating leadership roles in tech right now can feel like looking into a foggy crystal ball.
The rules of company building are being rewritten at pace, fuelled by advances in AI and the ripple effects on org design that come with the leaps in automation and agency. Founders are choosing to build smaller, leaner, more focused teams — and may seem indifferent to your leadership experience. That can be very disorientating.
The way companies create leverage has changed. Where leaders once drove impact through teams, today individual output is dramatically amplified. In the AI era, a smaller number of high-performing, tech-enabled operators can now deliver results that previously required entire departments. This shift reduces the dependency on people management as the primary engine of progress.
I hear from many mid-career leaders who, until recently, were squarely on a management track. Now they’re faced with a trickier market for leadership roles and a tough question: should I hold out for a senior position, or “revert” to an individual contributor role? It can feel like a career identity wobble — a return to the “what do I want to be when I grow up?” question that you thought you’d resolved.
But you are not unhireable, and your leadership experience is not irrelevant.
The hiring landscape has simply shifted. Here’s what’s changed — and the rethinking required to adapt.
What’s actually happening?
Founders are hiring fewer but higher-quality people — and this trend is here to stay. It addresses many of the growing pains of the last cycle: overhiring, high burn, organisational bloat, mass layoffs and cultural breakdowns.
The talent being hired now is high-output and autonomous. As a result, this means fewer people to manage, and fewer management roles overall. The middle layer — traditionally full of strong but less differentiated managers — is being thinned out.
The market is instead rewarding those who can do the work as well as direct it. Strategic capabilities paired with hands-on execution is the most in-demand combination. Particularly in early-stage and AI-native companies, it’s not about how many people you’ve led — it’s about what you can personally deliver and how quickly you can show results.
If your leadership track has been more about coordinating others vs. shipping work yourself, your value may not be immediately visible — not because it lacks merit, but because the market’s context has changed.
Rethink what leadership means
Try embracing ‘Leadership’ with a lowercase ‘l’: demonstrating the behaviours associated with leadership are more important than the title or position in today’s landscape. Every high-growth company creates opportunities to lead, but those opportunities aren’t always tied to headcount. Hands-on leadership is in; high-level abstraction is out.
Many experienced operators worry that stepping closer to the work signals career regression. In reality, it can be a powerful accelerant. If you’ve spent years leading from above, you may appear too far removed to thrive in today’s scrappier, pacy environment. And it’s not just early-stage startups looking for more hands-on hires who can do more with less, it’s also later stage scaleups and larger tech firms. We’re entering an era where headcount is no longer a marker of company success, and so it makes sense that managing people will no longer be the defining measure of leadership either.
Instead, think about leverage. Where can you have the most direct and indirect impact? How might you combine human insight with AI tools to scale your effectiveness? If you still love managing people — great. The best companies will still need brilliant, inspiring people leaders. But expect to go deeper with fewer direct reports.
The upside: More time to practise your craft, build real solutions and coach with less hierarchy.
Rethink the shape and optics of your role
This is a moment to get essentialist. What’s the differentiated value you bring? Move beyond titles (and any ego attached) and double down on your unique capabilities.
The roles worth chasing now may look blurrier, messier and less well-defined. That’s a feature, not a bug. Leaders who operate as generalists, general managers, or organisational ‘glue’ often have far more optionality than those with rigid functional identities.
It’s also okay — even strategic — to take an individual contributor (IC) role. Some of the most exciting, trajectory-defining roles I’m seeing right now don’t have a Head, Director or VP prefix in sight. In very early companies, founding operator positions are “super IC” roles with enormous leverage and visibility.
This isn’t a demotion — it’s a deliberate investment in your continued growth and relevance. Influence, accountability and trust will always matter more than team size.
The upside: Less vanity, more white space — and often a better match between your talents and your day-to-day work.
Rethink your narrative
Hiring managers are listening for evidence of ownership, adaptability, impact — and now — AI fluency. It’s not enough to say you’ve led — you need to show what you’ve built, fixed, scaled and augmented using AI.
What was the problem? What did you do? What changed? “I managed a team of 30” is less compelling than “I rebuilt the onboarding experience, halving ramp time and reducing attrition by 40%.” Your management experience should amplify your story — not be the story itself.
On your CV and in conversations:
- Lead with results, not reporting lines.
- Tailor your language — ‘VP of X’ can be reframed as ‘Operator who scaled Y’.
- Signal your readiness to get close to the work again.
- Showcase curiosity and humility.
The upside: A sharper, more compelling narrative that reflects the leader you are, not just the title you had.
Rethink the ‘track’ altogether
One of the most persistent myths is that career growth compounds in a straight line. But the leadership ladder is being replaced by something far more fluid. Careers are increasingly non-linear — and that’s not a problem to fix, it’s an opportunity to leverage.
That doesn’t mean people no longer want progression. You can still crave movement, expansion, growth. But the shape of that growth is evolving in new directions and the role playbooks of the past may no longer apply to you.
The slope of your growth matters more than the title. And in many cases, less formal structure means faster acceleration.
The upside: Fewer bureaucratic hoops, more interesting growth paths and momentum that matches your ambition.
This is a fascinating time to be building both companies and careers. It may feel like your leadership story is being interrupted. But in reality, it’s simply evolving. If you’re after the steepest ascent, sometimes the smartest move is to choose momentum over status.
