3 Critical Hires Most Startups Get Wrong and When to Make Them

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You are six months past the point where this hire would have changed the outcome. The work is getting done, just not well. The person doing it is capable, just not right for it. And somewhere between the quarterly review and the next funding conversation, someone will suggest it is time to bring in a specialist.

This is the pattern. Not a shortage of ambition or budget. The pattern is timing.

Three hires follow this pattern with remarkable consistency. Each carries a logic that makes deferral feel reasonable until it suddenly does not. And each one has a specific, identifiable signal at which the decision should be made.

Why Sequence Matters More Than Headcount

Startups tend to organise around the work in front of them. A developer is hired because there is a product to build. A sales hire follows when there is revenue to chase. The mistake is assuming that support functions follow the same urgency.

They do not. Each of the three hires below has a specific window. Miss it and you are not just delayed; you are solving a different, more expensive problem.

It is worth considering this alongside the wider question of how brand coherence and messaging clarity affect commercial performance, because the marketing and communications hire sits directly at that intersection.

The Marketing and Communications Hire: Made Too Late, Scoped Too Narrowly

The most common version of this mistake looks like this: a founder handles all external communications until the volume becomes unmanageable, hands it to the most articulate person on the team, then eventually posts a job description written by someone who does not fully understand what they need.

By this point, the brand has drifted. Messaging has been inconsistent. Sales are presenting the company differently to prospects than marketing is. Content has been produced without a strategic framework behind it.

This hire is not a marketing executive who can execute campaigns. It is someone who can build the communication architecture that everything else sits on. Getting it wrong costs more than the hire itself.

What makes this role particularly difficult to recruit for through conventional means is that the brief requires specialist knowledge to write properly. A generic job specification will attract generalists. The right candidate requires a recruiter who understands both the level of seniority and the nature of the function.

VMA Group, who have been placing marketing and communications professionals since 1978, are direct on this point: the businesses that get this hire wrong are usually the ones that treat a specialist recruiter as a last resort rather than a first call. By the time the brief lands under pressure, the margin for getting it right has already narrowed.

The timing signal for this hire is not when marketing becomes a problem. It is when the business is about to move into a phase where perception will directly affect commercial outcomes. That is earlier than most founders think.

The Senior Commercial Lead: Hired After the Damage Is Done

The second hire that follows a predictable late pattern is the senior commercial lead. In a founder-led business, this role is occupied by the founder by default. It works in the early stages when relationships are close and deal cycles are short.

Then the business scales. The pipeline is larger and harder to manage personally. Sales processes that were informal become inconsistent. New team members close at lower rates because institutional knowledge was never transferred.

The commercial lead should have been hired before the pipeline required one. Instead, the hire is made reactively, and the new person spends their first months unpicking processes never designed with scale in mind.

The right commercial lead is someone who can install rigour into a function that has operated on instinct. That requires a different profile, a different salary expectation, and usually a different type of search.

The timing signal is the first time a deal is lost because of process rather than product. That is the window. Most businesses wait for the second or third time. By then, the cost in revenue and momentum has already been paid.

The Operations Function: Invisible Until It Is Critical

The third hire creates the least urgency right until it creates the most. At the early stage, decisions sit with the founder, finance is outsourced, and things get done because coordination is easy. Then the headcount grows past around 25 people.

Decisions slow down. Onboarding becomes inconsistent. The founder is acting as a coordinator rather than a leader. This is a structural problem, not a people problem.

The right operations hire is someone who can design systems, not just follow them. They are harder to find and harder to describe in a job posting, which is why so many businesses under-hire for this role and pay for it later.

The timing signal is the first time the founder notices they are managing coordination rather than making decisions.

The Cost of Waiting

What connects these three hires is not the function. It is the pattern. Each one is deferred because the immediate cost is invisible. The marketing function limps along. The commercial pipeline gets managed, just less effectively. Operations hold together, just not cleanly.

The cost accumulates quietly. By the time it becomes visible, it has already been expensive. The businesses that absorb this cost rarely make one identifiable mistake. They make a sequence of reasonable-looking decisions, each deferring the difficult one. These three roles have a predictable window, and recognising it earlier changes outcomes.

Making the Decision Earlier

The businesses that navigate these hires well share one characteristic. They treat hiring in these functions as a strategic decision rather than an operational one; asking not just who they need now, but who they will need when the next phase arrives.

When these hires are made at the right moment, they accelerate everything else. When they are made late, they absorb time, resources, and momentum the business cannot easily recover. Act quickly, the window is usually shorter than it looks.

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