What A CEO Worth $150M Taught Me About Sales

Jan '23 in Other

This post teaches you how a CEO worth $150M thinks about Sales.

QUICK BACKGROUND

In 2019/2020, I worked at one of Toronto's fastest growing software startups. Zoom and Shopify are clients. Company was just valued at $1.2B. (65X valuation...) Head of Sales was 26 and had already sold two companies. CEO was 33, and had also sold a few companies. It was an amazing environment. I booked multiple 1:1 meetings with the CEO to find out what he knew that I didn't. Here's what he taught me about improving my response rate and sales.

CLARITY/BE CONCISE & THE NEWSPAPER METAPHOR

You have to get right to the point and indicate how you're going to bring some clear-tangible value. His exact words were 'imagine every word you write is incredibly expensive and you are incredibly cheap.'

His metaphor was this: Think about sales through a newspaper metaphor:

The more senior someone is in an organization, the more they just communicate and understand headlines; they only understand and will only listen to the 8 words that are the highlight of today’s story,
The more junior someone is in an organization, the more they front load information in huge text bodies and paragraphs. They’ll give you all this information and then end with the headline,
Senior people, if they open an e-mail, and see something that extends beyond a couple lines––they’ll just ignore it immediately. Complete default ignore.
If you can craft a picture of the e-mail being really tight, really small, it’s more likely to be opened and responded too and it’s a sign of respect––you’re not taking time away from them.

For me specifically, the sweet spot is 70-125 words. Any longer is playing with fire. I booked meetings with CEOs of big companies with 70 word emails.

VALUE

You must bring Value. But wait, what actually is Value? It's a buzz word that gets tossed around a lot in the sales/entrepreneur world and since I like asking stupid obvious questions, I asked him: What does Value actually mean to you? His exact words:

'Value is a reflection of the extent to which I’ve learned something new. The root of this is really about teaching something new to someone. It’s a reflection of expertise and then being able to instil new learning in someone who doesn’t have it. Value is a reflection of deep understanding.'

In the context of sales emails. Value is some tangible, measurable, significant increase in some major arena. So long as it's clear, specific and beneficial - you're in the clear.

TRANSPARENCY

Be really clear what the intention is upfront - when things are unclear, people assume the worst, and ignore you. His exact words: Be super transparent about what you're asking for at the beginning. It’s 2019, transparency is king, gone are the days where there’s like subtlety or implicit sales pressure. That role is dead.

PERSONALIZATION IS CRITICAL

You must personalize the first line of your email so it shows you've actually done your homework to differentiate yourself from the millions of other people asking for something. Do you understand my company/where its going/what it’s challenges are/is it clear that you care about this relationship?

If it's clear you’ve done your homework and that you understand the business, that will always get someone’s attention - not a revolutionary idea. It’s a huge yield for a small effort. Last key point is your personalized first line can't be longer than a sentence. Don't write a paragraph. Make it personal, human and concise. Jokes work too if they're actually funny.

ATTITUDE/BE DEFERENTIAL/BASIC COURTESY- GIVE!

If you want something out of someone and you don’t have any leverage, you’ve got to be deferential. You’ve got to make it clear that you’re putting in more effort than they are, initially.

Another way to think about this is an Effort Exchange - there's a market that’s happening when you're engaging in sales . You want to make sure that the prospect is always winning - that they’re always getting more from you than what they’re giving. There needs to be an exchange but in the early days, it shouldn’t be an equal exchange. It should be a lot of work that you’re doing up-front for a little bit of return because the return on their investment is super high. Most sales-cycles breakdown in the early funnel because people assume a tit-for-tat relationship or it’s heavily skewed in favour of the seller when the buyer doesn’t get anything or what the buyer is giving far outweighs what the seller is asking for.

It might be valuable to think about that ratio, but it should be an obvious trade for the buyer - "I’m giving 1 point of value and I’m getting 20 in return…I’ll play”

BE SPECIFIC

Don't message people and tell them you have great ideas to help them do 'xyz'. Tell them specifically. Example of what doesn't work: "Hey Ms XYZ, I have some great ideas around customer support". What does that mean? I don’t need ideas - I need things I can do.

JUST A GREAT GUY

Last key point. The CEO was such a nice guy. So approachable. So humble. So nice. He made you want to work for him and you felt like he actually cared. It matters to point this out because there's SO much hate for the rich and successful and media organizations 100% feed into this. It's tangible evidence that the most succesful person I know is actually very loving, kind, and warm.

That's it.

THE END

Hope that's helpful y'all! His notes helped me write effective sales campaigns. I brought in 5 new mid-market companies for the company from pure cold-emailing. Total value of those contracts was probably $250K per year. The above works. Happy to answer any more questions and elaborate. Happy hunting!

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