Author: John Clifton

What Founders Get Wrong When Briefing an Executive Search

Posted on by John Clifton

A better brief doesn’t just save time – it changes the quality of the hire

Most founders approach an executive search the same way they’d approach any other procurement decision. They have a role to fill, they know roughly what they’re looking for, and they brief a search firm with a job description and a list of requirements. The search begins. Candidates are presented. A hire is made.

The problem is that this approach optimises for speed and activity rather than fit and outcome. And in senior leadership hiring – particularly in fast-scaling AI infrastructure, data, and cloud businesses where the margin for error is small – a weak brief is usually where a mis-hire begins.

After 15 years working on executive search in high-growth technology businesses, the same briefing mistakes appear time and again. Here’s what they are, and what to do instead.

Starting with the title rather than the problem

The most common mistake is beginning with an org chart rather than a business challenge. A founder decides the company needs a CRO, or a CPO, or a VP of Engineering, and frames the brief around that title – the seniority required, the team size, the reporting line.

What usually gets skipped is the harder question: what specific problem is this person being hired to solve?

That question has a different answer in every business, and the answer matters enormously for the type of leader you actually need. A CRO hired to build a repeatable enterprise sales motion from scratch is a fundamentally different person from a CRO hired to scale an existing team across new geographies. The title is the same. The role is not.

A brief that starts with the title will attract candidates who fit the shape. A brief that starts with the problem will surface candidates who can actually solve it.

Describing the ideal candidate rather than the ideal outcome

Closely related to the above is the tendency to build a brief around a candidate profile – years of experience, previous employers, educational background, technical skills – rather than around what success looks like once someone is in the role.

This matters because profile-led briefs create a filter that feels rigorous but often isn’t. They reward pedigree over capability, and they frequently exclude the best candidates for the actual role. In AI infrastructure businesses particularly, the leaders who perform best in complex, technically demanding commercial or operational roles often don’t come from the obvious backgrounds. They’ve built things from scratch at less well-known companies. They’ve navigated transitions that weren’t linear. They’ve developed deep sector fluency that doesn’t fit neatly into a CV summary.

Defining what success looks like at 6, 12, and 18 months is a far more useful exercise than defining what the ideal CV looks like. It also produces a much better brief.

Underestimating how specific the context is

AI infrastructure businesses are not generic technology companies. The sales motion is different. The buyer relationships are different. The product complexity is different. The organisational culture – typically technical, often founder-led, usually moving very fast – is different.

Founders sometimes brief a search as though any strong senior leader from a technology background could step in and perform. In practice, the context mismatch is one of the leading causes of early failure in senior hires. A leader who has spent their career in enterprise SaaS will approach an infrastructure sales organisation very differently from someone who has built and scaled a technical go-to-market in a similar business. Both might look strong on paper. Only one is likely to work.

A good brief conveys the specificity of the environment honestly – including the parts that are hard. The pace, the ambiguity, the founder’s continued involvement, the technical depth required to earn credibility internally. Sanitising the brief to make the role sound more appealing rarely ends well.

Treating the search firm as an order-taker

Many founders approach a search engagement as a relatively passive transaction. They provide the brief, and the search firm goes and finds people. Updates arrive. Candidates are reviewed. A hire is made.

This model produces mediocre outcomes, even with a good search firm. The best executive searches are collaborative. The founder’s insights about the business, the team, the competitive context, and the nuances of the role are essential inputs – not just at the briefing stage, but throughout the process.

More importantly, the most valuable thing a search partner can offer isn’t just access to candidates. It’s an honest, informed perspective on the market – on what’s realistic, what the competition is paying, what profile of leader is actually available, and whether the brief as written will attract the right people. That perspective is only useful if the relationship is open enough for it to be shared plainly.

If a search firm never pushes back on your brief, that’s not a sign they agree with you. It’s usually a sign they’re not adding much value.

Not thinking about what comes after the hire

The final briefing mistake is treating the search as complete when an offer is accepted. Most founders – and most search firms – move on at this point. The role is filled. The next priority takes over.

But in senior leadership hiring, the real risk sits in the first year. The quality of the brief determines not just who gets hired, but how well the business is set up to support that person once they join. Clarity on the mandate, the success criteria, the founder’s ongoing involvement, and the boundaries of the role are all things that should be established during the briefing process – not figured out after the hire starts.

Common points of failure that trace back to a weak brief:

  • The new leader interprets the mandate differently from the founding team, and no one discovers this until significant damage is done
  • Unrealistic timelines are set because no one modelled what a realistic ramp looks like for this specific role
  • The founder and the new hire have different assumptions about how decisions will be made, because this was never made explicit
  • Early underperformance triggers a loss of confidence before the leader has had a genuine chance to build foundations

None of these are inevitable. Most of them are avoidable with a brief that is specific, honest, and grounded in outcomes rather than activity.

What a better brief looks like

Getting the brief right doesn’t require more time – it requires a different focus. Instead of starting with the job description, start with the business problem. Instead of describing the ideal candidate, describe what the business looks like when this person is performing well. Instead of listing requirements, define the conditions for success and the environment the hire will be operating in.

And choose a search partner who will push back on the brief rather than simply execute it – one who brings genuine market intelligence to the conversation and who stays engaged beyond the hire itself.

In a market moving as fast as AI infrastructure, senior leadership decisions carry outsized risk and impact. The brief is where that risk either gets managed or ignored.

Third Circle Partners works with growth-stage and investor-backed AI infrastructure, data and cloud businesses on senior leadership hiring. Before any search begins, we invest in alignment around the problem, the conditions for success, and what good looks like – because a better brief produces a better hire. A significant proportion of fees are tied to milestones during a leader’s first year.

From Founder-Led Sales to Commercial Leadership: How to Make the Transition Without Losing Momentum

Posted on by John Clifton

One of the most critical – and most mishandled – inflection points in a scaling infrastructure business

There’s a moment that almost every founder of a high-growth technology business reaches. The early customers are in. The product is proven. The pipeline is building. And it becomes obvious that the founder can no longer be the primary driver of commercial growth – there simply aren’t enough hours, and the business needs someone whose entire focus is revenue.

So they hire a commercial leader. And far too often, within 12 to 18 months, that hire has either left or is quietly underperforming. The pipeline stalls. The founder steps back in. The business loses six months, sometimes more.

This pattern is so common it almost feels inevitable. It isn’t. But avoiding it requires understanding why it keeps happening – and what the transition actually demands.

Why founder-led sales is so hard to hand over

Founders who sell well are usually doing several things at once that they aren’t fully conscious of. They carry deep product knowledge. They have a point of view on the market that resonates with technical buyers. They can go off-script in a conversation and still land the deal. They know which customers to prioritise and which ones will drain resource. And they have credibility that took years to build.

None of that transfers automatically to a new hire on day one.

The mistake most founders make is assuming that a strong commercial leader will be able to replicate what they’ve been doing – just at greater volume. In reality, the incoming leader is starting from scratch on context, relationships, and organisational trust. If the handover isn’t structured carefully, the seams show immediately.

The wrong hire for the right reasons

AI infrastructure businesses often make a very specific hiring error at this stage. Under pressure to scale, they look for someone who has run a large sales organisation at a well-known technology company. The CV is impressive. The references are strong. The candidate talks fluently about pipeline management, territory planning, and revenue operations.

What they may never have done is sell a deeply technical infrastructure product to a buyer who is simultaneously a customer and an evaluator – someone who needs to trust the product architecture before they’ll commit to the commercial relationship.

Enterprise SaaS sales and infrastructure sales are not the same discipline. The cycle is longer, the evaluation process is more technical, and the relationships that matter are often at engineering and platform level before they ever reach procurement. A leader who has spent their career selling software to business buyers will struggle to build credibility in this environment, regardless of their track record elsewhere.

The talent exists. But finding it means knowing where to look and being honest about what the role actually requires.

Setting the new leader up to fail

Even when the right person is hired, the transition often goes wrong because of what happens after the offer is accepted. A few patterns come up repeatedly:

  • The founder remains involved in key deals but without a clear agreed framework for when and how – creating confusion about who owns what
  • The new leader is given ambitious revenue targets but insufficient time to build the foundations required to hit them
  • There is no structured onboarding into the product, the technical culture, or the nuances of the existing customer relationships
  • Early tension between the commercial leader and the founding team goes unaddressed until it becomes a serious problem
  • The board treats the first six months as a trial rather than an investment – making the new hire’s position feel precarious before they’ve had a real chance to perform

Any one of these is damaging. Several of them together is usually fatal to the hire.

What the transition actually requires

Getting this right starts well before the search begins. The founding team needs genuine clarity on what they’re handing over, what they’re retaining, and what success looks like at six, twelve, and eighteen months. This sounds straightforward. In practice, it’s rarely done rigorously.

A few things that materially improve the outcome:

Realism about the candidate profile. The right commercial leader for a Series B AI infrastructure business is probably not the same person who would thrive at a scaled enterprise software company. Sector fluency, technical credibility, and the ability to build from a relatively early stage all matter more than a large team or a famous employer on the CV.

A proper handover of context. Key customer relationships, pipeline history, deal dynamics, product positioning, and the technical nuances that underpin the sales conversation – all of this needs to be transferred deliberately, not assumed.

A defined role for the founder. The founder doesn’t disappear overnight. In many cases they remain a powerful asset in senior customer relationships or strategic deals. But the boundaries need to be explicit, agreed early, and respected.

Patience on the timeline. A strong commercial leader in a complex infrastructure business typically needs six to nine months before they’re operating at full effectiveness. Boards and founders who expect a step-change in revenue at month three are usually disappointed – and often draw the wrong conclusions.

Active alignment in the first year. The most valuable thing any external partner can offer is a mechanism for surfacing tension early – between the hire and the business, between expectations and reality – when there’s still time to course correct rather than part ways.

The cost of getting it wrong

A mis-hire at commercial leadership level in a scaling infrastructure business is not just expensive in financial terms, though it is that too. It sets the go-to-market motion back by at least a year. It damages momentum at exactly the moment when the business should be accelerating. And it often leaves the founder more reluctant to hand over commercial ownership the second time around – which compounds the problem further.

The companies that navigate this transition well tend to have one thing in common: they treated the hire as a strategic decision, not a resourcing problem. They invested time in defining the role properly, found someone with the right sector and stage experience, and stayed actively engaged through the critical early period rather than assuming the work was done when the contract was signed.

That’s a higher bar than most businesses set. But in a market moving as fast as AI infrastructure, it’s the only bar worth setting.

Third Circle Partners works with growth-stage and investor-backed AI infrastructure, data and cloud businesses on senior leadership hiring. A significant proportion of fees are tied to milestones during a leader’s first year – keeping the focus on outcomes, not just placements.

Why AI Infrastructure Companies Get Leadership Hiring Wrong

Posted on by John Clifton

The mis-hire pattern that keeps repeating – and what to do about it

AI infrastructure is moving fast. GPU clouds, data platforms, sovereign compute, next-generation storage – the companies building this layer of the stack are scaling quickly, attracting serious capital, and under real pressure to grow. And as they grow, they hire.

The problem is that many of them hire badly. Not through carelessness, but through a set of recurring mistakes that are almost predictable once you’ve seen them enough times. After 15 years working at the intersection of executive search and high-growth technology businesses, the same patterns keep emerging – particularly in companies transitioning from technically excellent to commercially scaled.

Here’s what usually goes wrong.

Hiring the profile, not the problem

The most common mistake is starting with a job title rather than a genuine leadership challenge. A company decides it needs a CRO, or a CPO, or a VP of Engineering. It builds a brief around credentials – years of experience, previous employers, sector pedigree – and goes looking for someone who fits the shape.

What gets missed is the specificity of the problem. AI infrastructure businesses are not generic technology companies. The sales motion for a GPU cloud platform is fundamentally different to selling SaaS. The product challenges in a data infrastructure business at Series C are nothing like those at a scaled enterprise software firm. Hiring someone who looks right on paper, but who has never navigated this particular type of complexity, is one of the most expensive mistakes a founder can make.

The brief needs to start with the business problem, not the org chart.

Optimising for the interview, not the role

Technical founders are often very good at assessing technical capability and very under-equipped to assess commercial or operational leadership. This creates a specific bias: candidates who are articulate, confident, and impressive in a room get hired. Candidates who would actually be brilliant in the role – but who are more methodical or less performative in a 45-minute conversation – get passed over.

Search processes in infrastructure businesses often lack structured evaluation frameworks. They rely too heavily on gut feel, reference checks from within a narrow network, and a handful of informal conversations. The result is a hire that felt right at the time and unravels in the first year.

The most capable leaders in complex infrastructure roles often don’t interview especially well. The best interview candidates don’t always last.

Underestimating the transition from technical to commercial

Many AI infrastructure companies are founded by deeply technical people. That’s a strength. But it becomes a liability when the business needs to shift from product-led growth to enterprise sales, or from a handful of design partners to a scaled go-to-market motion.

This transition requires a very specific type of commercial leader – someone who can credibly engage a technical buyer, navigate complex procurement, and build a repeatable enterprise sales process from scratch. Most CROs from traditional SaaS backgrounds can’t do this. Most technical founders don’t know how to assess whether someone can.

The talent pool exists. Finding it requires knowing where to look and how to evaluate it.

The risk sits after the hire, not before it

The biggest structural flaw in how most companies approach senior hiring is the assumption that the job is done when someone accepts an offer. It isn’t. The real risk in any leadership hire sits in the first 12 to 18 months – the period where strategy either translates into execution or it doesn’t.

Most search firms disappear at this point. The fee is collected, the next search begins, and the new hire is left to navigate onboarding, alignment, and early delivery with very little external support. In fast-scaling infrastructure businesses, where context is complex and the pace is relentless, that gap is where mis-hires happen.

Common failure points in the first year include:

  • Misalignment between the leader’s mandate and what the founding team actually wants
  • Insufficient onboarding into the technical culture and product context
  • Pressure to deliver commercial results before the foundations are in place
  • No structured mechanism for surfacing early tension before it becomes a problem
  • A lack of honest feedback loops between the new hire and the board

What better looks like

Getting leadership hiring right in AI infrastructure requires a different starting point. Before a search begins, there needs to be genuine clarity – on the problem being solved, the conditions for success, and the type of leader who has actually navigated similar transitions before.

The search itself needs to go beyond the obvious candidate pool. The people who perform best in these roles are often not actively looking, are not on the usual radar, and require a network built specifically around this part of the market.

And the work shouldn’t stop at placement. The most valuable thing a search partner can offer is continued alignment between the hire and the business – through the onboarding period, the first milestones, and the moments where early course correction is still possible.

Most firms aren’t built to do this. The incentives don’t support it. But in a market where a single mis-hire at senior level can cost a company a year of momentum, it’s the only model that makes sense.

Third Circle Partners works with growth-stage and investor-backed AI infrastructure, data and cloud businesses on senior leadership hiring. A significant proportion of fees are tied to milestones during a leader’s first year – keeping the focus on outcomes, not just placements.