How To Win New Business When You’re Not A Natural Salesperson

It all starts with your thoughts and language ...

Some Founders & CEO’s have a particular description of what ‘sales’ is and a particular image of what a ‘salesperson’ looks like.

They describe sales as ‘influencing and convincing’ and the image of a ‘salesperson’ as having one or more of these attributes:

  • A natural (at sales)
  • A self promoter
  • An extrovert
  • Pushy
  • Closer
  • Well connected (have a ‘black book of prospects’)
  • Influencer
  • Able to convince
  • Cold-caller
  • Relentless at following-up

The problems with this description and image are three-fold:

1 - Sets an Unhealthy Sales Philosophy & Culture

If your definition of sales is ‘influencing and convincing’ then you're setting on a trajectory where your marketing ‘voice & tone’ is ‘pushy’ and ‘salesy’ and your sales culture becomes ‘get a sale at any cost’.

A sale at any cost - usually results...

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Get In The Head Of Your Buyer Before You Get In The Head Of Your Buyer

No this Title is not a typo …

As a founder, you can get in the head (& heart) of your ideal buyer twice, but only if you do it in the right order …..

Here's the method to the madness (of the title)


As a function of influence, you need to get in the head (& heart) of your ideal buyer, so you are top of mind and you have earned their trust.

But before that ...

As a function of empathy, you need to get in the head (& heart) of your ideal buyer, so you understand their aspirations and their constraints.

So the first time you get in the head of your buyer you are there to observe, listen, learn and empathise. The second time you get in their head you are there to influence, earn trust and be top of mind.


A critical lever for growth is your communication in all its forms including for:

  • Marketing
  • Public Relations
  • Pre-sales
  • Sales
  • Post Sales
  • Customer Success

By ‘getting in the head of your buyer, before you get in the head of your buyer’...

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10 Sales Strategies That Closed 100+ Australian Enterprise Customers & Generated Multi-Million Dollars In Revenue

As the Founder & CEO of my last tech venture, Contexti - a data analytics (big data/AI) company serving mid-market and large enterprise customers in Australia, I had to devise and execute a go-to-market strategy against a number of challenges.

Before starting this venture I had spent the previous 5 years living and working abroad in Silicon Valley, USA with another venture and I had started this business having no expertise in cloud, data analytics or data science.

So I was literally an outsider on all accounts, I was new (again) to the country and new to the industry.

To support our vision of being ‘AsiaPacific’s premier big data analytics company’ and our mission to ‘help customers create value from data’ , I had to figure out:

How do we get leads?

  • We did not have a large marketing budget
  • We did not want to cold-call prospects
  • We did not trust a ‘lead-generation’ service provider will do our brand and voice justice

How do we earn...

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The One Thing From A $200 Million Exit & Why It’s Critical For Your Venture

fintech growth sales scaleups Nov 13, 2020

I was listening to Shola Akinlade, Co-Founder of PayStack, a Nigerian-based Fintech / payments company which was recently acquired by Stripe for $200 Million.

As always it was a great interview by Andrew Warner of Mixergy and I highly recommend you listen to the interview with Shola and subscribe to the Mixergy podcast (links below).

Many things were super-impressive from Shola’s story but the one thing that stood out for me was Shola saying….

“I spoke to the first 300 customers of PayStack”

Reflecting on my own experience and of the founders I advise, when seeking growth we often think the answers exist on the outside (external).

For example …

  • We look at what the competition is doing so we have feature parity in our product (and product roadmaps); or

  • We hunt to acquire new logos to add to our customer list; or

  • We consider changing our marketing or PR strategy or service providers and so on.

While all of these and many other ‘external’...

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