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  • Writer's pictureRobert White

Hiring a Head of Sales for a scale-up

In a recent Linkedin poll asking which role was the hardest to hire for, overwhelmingly people voted for Head of Sales. So, why is this such a hard role to hire?


Having successfully recruited for this role multiple times (and some unsuccessful campaigns too), here are key things I've learned over the years.


Defining the role is the most crucial part of the process. Too often, founders haven't articulated what they want clearly enough.


While this might seem obvious, we've encountered people who think they need a Head of Sales, but are actually need a Sales Executive. Here's a simple decision chart we use to help people discover what they actually need:



Whilst this isn't exhaustive, it provides a starting point to build the ideal of the profile. Finding a great Head of Sales is extremely difficult, especially for a scale-up, so be sure you truly need this role.


The ideal candidate will possess a strong mix of sales experience, leadership abilities, relevant industry knowledge, and a deep understanding of the challenges that come with scaling a sales function. They should not only excel at sales themselves but also be highly capable of building and managing a successful sales team.


The CV

A CV can never tell the whole story, especially in sales. There are often multiple reasons, outside their control, why salespeople move on from companies. It's common to see setbacks in a Head of Sale's CV.


This might initially be seen as a negative, but the key is to delve into their experience and identify what they learned from it. A candidate who doesn't take some responsibility for failures is a red flag. However, those who can articulate why things went wrong, what they learned, and how they'll do things differently next time are excellent additions to your team.


A growth mindset is crucial during a scale-up process, and people with the emotional intelligence (EQ) to self-reflect will be highly likely to succeed in the right environment. This is where working with a trusted recruiter can be advisable to save you time. A good recruiter will have conducted due diligence on reasons for leaving or shorter roles on the profile and be able to give you the full picture, along with how the candidate discussed the situation 


At interview

A good Head of Sales will streamline the interview scheduling process. They'll be accommodating on their end, making it easy to find a mutually convenient time.


Top candidates will be able to articulate revenue figures effortlessly and, crucially, provide context for their personal impact. Beware of candidates who say "we delivered" or "we implemented." This often indicates they were part of a team that achieved results, rather than the driving force behind the initiative, which is the quality you're seeking in a great Head of Sales.


One factor to consider: a great Head of Sales will be able to list contacts and previous employees they could influence on day one of joining your scale-up. This is a red flag if a candidate cannot demonstrate this ability.


A curious mindset is essential in sales, and even more so for a sales leader. Pay close attention to the questions they ask you and what they're interested in learning about your business.


Salary negotiation and close

By definition, a good sales leader will excel at closing deals and negotiation. During the interview process, expect the best candidates to confirm and reconfirm salary expectations and package details upfront. If they leave this until the offer stage, proceed with caution. No one likes surprises, and this behaviour can offer insight into how they might handle client negotiations on your behalf.


Working with a trusted recruiter can make this process much easier. They can act as a third party to test scenarios and package details, ensuring you get the best deal for both sides.

Finally, a good Head of Sales will likely have multiple options when considering a new role, so be prepared to sell them on your company. Explain why your organisation is the best place for their next career step. Understanding their motivations and goals, and how you can help them achieve them, are crucial steps to successfully hiring your next sales leader.

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