A series of unfortunate (sales) events (Or the biggest mistakes founders make and how to avoid them)

Back in the very first GTM series, we set out a few how-to guides – practical advice on sales & customers to support the Seed to Series A Entrepreneur. Now we want to dig into a few histories, or rather a few stories…you know…the one where someone looks back at what has happened, explains their lessons learnt and optimistically looks to the future knowing a better path.

Or rather sort of.

Let’s begin the story with the simple Seed to Series A – a series of unfortunate (sales) events.

You’ve got baggage

You’ve been there, seen it, done it and felt the pain. With your industry experience, market knowledge and laser insight you might as well BE the customer.

Except you’re not.

You’ve come at the problem with a whole bunch of assumptions which might be right – but very well might not. It’s called assumptive bias and it can blind you to the actual needs of the actual customer.

By believing what you see through your rose-tinted glasses, your view doesn’t match the reality of your customer base. The problem you are solving might not be one they actually have. The value you have put on a particular pain point might be dwarfed by something far more pressing.

The key failing here is not to stop and challenge your own preconceived ideas. You need to test your hunches and instinctive biases against the types and personas of the customers you are targeting.

By identifying what are truly their biggest challenges and pain points you can shape your product accordingly and narrow your focus on the highest value customers.

Spotlight, but no illumination

There are many parts to the sales process and getting them all working like a well-oiled machine is a challenge. Pricing, transactions, demand marketing – if you can see an aspect that is problematic it seems sensible to focus your energies on fixing and optimising it. The easy mistake to make here is to over-focus on that one spot and fail to see it as part of the wider, integrated whole. All the components in the sales process are related, with each having a bearing on the others.

Focus instead on the particular pain point you are trying to solve for your customer. You need to evolve your product to address that problem and doing so informs your sales process – not the other way round. I see companies placing too much emphasis on process or a particular part of it, using tools such as Excel, SFDC and Pipedrive as their saviour. The tool is not the answer, a holistic approach is.

Holding out for a hero

When it’s clearly so easy to get the emphasis and focus of your sales efforts wrong, it makes sense to bring in a guru who wouldn’t make such mistakes. Someone who’s been a CEO or a head of sales at firms she’s built up and successfully sold. Hiring a sales expert with a glittering track record seems like a no-brainer, right? It means you and your co-founders can get back to the important work of developing your product, confident in the knowledge that sales will soon be going stratospheric.

Except your new sales hotshot doesn’t have that same early-stage fire you have – the passion that has already engaged your first customers or development partners. They want to implement whatever drove those explosive sales that are probably still a little way off for your company. They’ll call up their network and try and sell what they think your product should be, and will very likely lean on your engineers to bend it into that more familiar shape.

Failure is going to leave a bad taste for you and your dejected sales guru, with time and money down the drain. The truth is, founders remain the best sellers of their products at the very early stage of a business. While a product is being shaped and crafted through working closely with customers

Can’t let it go

A mistake that’s just as easy to make as handing off sales when your company is not quite ready is not handing off sales soon enough. Confusing? Well, striking this balance is tricky but important at such a crucial moment in the development of your business.

Founder-led sales are enormously important and the best way of setting out with your customer at the heart of your organisation. There will come a point, though, where the time is right for hiring to allow the founders to focus on execution.

Straightening it all out

Perhaps the final potential mistake to avoid is to take these as singular pitfalls to look out for and address. In actual fact, these common problems are very often interlinked and can have a cascading impact that ends up in a tangled mess that’s hard to unravel. The result can be a lack of traction that you can’t understand because there is no one thing that is obviously wrong.

The stage your business is at, the level of customer development you have reached and the resources you have will all be factors affecting how you navigate past these common mistakes.

The best approach is to focus on the customer group with the most significant pain point and make them the focus of your efforts.

From mistakes to lessons to sales that can scale

So, hopefully this post has highlighted the common problems that trip up founders when it comes to developing the sales function in their companies during the 18-month journey from Seed to a Series A funding round.

Over the next few posts we will take a look back into history to see what we can learn from the evolution of sales in the IT and software space. The days of flogging stuff to unwitting customers – regardless of whether it’s stuff they actually want or need – are thankfully long gone. So we’ll explore how putting the customer at the heart of organisation isn’t just the latest sales fad but the only way to really gain traction and how that works as you begin to scale


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