Time for Sales to Change

Paul O'Brien
6 min readJul 16, 2024

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Has the internet forced that it’s time for Sales to change? I think so, but bear with me because I know a lot of successful salespeople, and I suspect they’re going to disagree with me; let me set the stage a bit, and hell, bring on some disagreement because if we don’t spark a conversation, then what fun are we having??

I’ve posed the following idea before; that the internet broke everything (over the last 25 years) and we’re only now starting to meaningfully develop the solutions society wants, having suffered through the consequences of the early days of wrestling with what the internet changed. In time things will be better but until then, we’ve had to deal with, among many more things, broken social media, abuse of SEO, the end of copyright thanks to a global digital economy. What happened with blockchain, and cryptocurrency, was a kneejerk reaction to misunderstanding the internet, and what’s happening with AI now is just another growing pain. eCommerce caused us to wrestle with massive amounts of fraud, email promised a better world and yet now we’re deleting hundreds of spam messages every day, Marketing was completely screwed by CMOs who didn’t understand digital, and so here, I want to ask what you think of Sales.

Sales is a bit of a sore spot for me. I’m not personally any good at closing business and I abhor meetings, I value my time unless there is a problem — so sales taking up my time is an affront. Despite that, I’m good at reaching and connecting with people, teaching, and influencing, and advisors constantly push that I’m very good at sales… and yet the previous statement remains true. Maybe it’s not that sales is a sore spot but rather that I expect it to work the way the internet makes possible, frustrating me with the fact that it doesn’t.

Sales too was broken by the internet

I’m an internet baby. One of the oldest in society to know the internet intimately, while today’s generations have always had it, I’m among the few who can say I’ve had it since it started. As a result, I find I think differently about what I expect of founders, politicians, marketers, investors, and salespeople, because of what is valid to expect is in place because of what the internet can do.

Last week, I had a founder ask me about cold outreach (both of angel investors and finding prospects) and it was that inquiry that pushed me over the edge to convey more clearly: The worst things you can do in a cold outreach, I report all as spam:

  • Can we talk?
  • Can I send you a pitch deck?
  • You need what we offer
  • We can make things better for you
  • We have a lot in common, we should connect
  • Can I pick your brain?
  • I see we know a lot of the same people…
  • Investors are making 7% returns, I thought you’d be interested
  • We’d like to explore possibilities
  • Do you have time to discuss any synergies?

I’m sure you’ve probably messaged someone with something like that.

On the few occasions where I’m willing to take a moment to reply to some, I’ll usually say something like, “go ahead and tell me here what you have to offer,” and when I’m met with someone who says, “it’d really be best for us to talk,” or that, “we should find a time to set up a demo,” I lose my cool.

In effective networking, your job (reaching out), is first providing value.

And in such outreach, it’s immediately clear that you did not.

Get to know your target — the person, the business, etc. Then, DO something for them. It could be (because who knows what works) something as simple as providing some new research relevant to them.

What’s the key to startups? Execution Not talking. Not meeting. Doing.

And despite that understanding, it’s astounding to me in networking or Sales, people want something before giving something. Even Sales is wanting something without creating any value — you are asking for my time.

Make my time worthwhile by leading it forward first. How you might do that is up to whatever works best for you; just appreciate that even your audience merely reading your messages, means they’ve already done something for you at their expense — make sure that message creates value if you want more.

This discourse begged the question I have for us today, I was asked, “but then what do we do?”

To that end, I put together a list that might help change sales but guiding what might be better. Again, HUGE grain of salt, I don’t like doing sales and by no stretch would it be valid to say I’m an expert nor experience; but I will say this, I don’t take your call, I report your cold email, and most of those messages are failing.

  1. Create value. A business selling something is not value created, it’s a cost you want others to bear, in order to be sold.
  2. Know your audience. This isn’t a marketing process of profiling customers, understanding your buyers, nor targeting your messages, I mean that in sales, today, actually KNOWS the person whose attention you’d like.
  3. Impart some of that value to your audience. Your target. It could be something as simple as tagging them because what you did is meaningful to them. It could be even simpler, studying them so that you don’t waste their time. It could be substantial, promoting them. Notice, I didn’t lead with the OLD practice of first knowing or profiling your customer, I led with first creating value — if YOU (not your business nor your employer) are not personally doing something value, what you have to push on someone from the business isn’t value. The internet has created a world in which you personally have no excuse not to create some value so that when others make time for you, you can impart that. THEN figure out for whom you should do that.
  4. Engage with your audience. Business is built on relationships. So, if you cold reach, it tells me you don’t give a damn about me, you’re just trying to close a deal — hence, spam. Comment on posts, reply to tweets, or share an article I wrote. It costs you nearly nothing to engage… And you’re asking of me time and consideration.
  5. A CRM is free. If you aren’t using one, if your business or company doesn’t have one (and you aren’t demanding it be in place), shame on you. If you call, email, or message ANYONE and you haven’t already determined that they are interested by way of their engagement with something, shame on you.
  6. Communicate your message and value proposition. Do not ask for time! Tell me what you offer. Tell me why I’d care. Do that IN your outreach with no expectation of anything from your audience. If you need to “explore it,” do discovery, “talk about potential synergy,” or “pick my brain,” as you’re trying to get a meeting to do that, it tells me you didn’t bother with 1–4. Get across the value proposed, in the way I’d value it.
  7. Meet on their terms. Don’t send a calendly and make them figure out in some passive aggressive, “I’m being helpful,” assertion, when is good for you both, respect that your target is busy and their time is valuable, meet on their terms. More, don’t be that person who is unwilling to engage on their terms (people who reply to a request for more information, saying we really need to talk or do a demo, stop — you lose, immediately, when you do that).

If you don’t know how to reach someone in these ways, you’re practicing an old sales methodology that still believes getting out dozens of cold calls, spamming email, or booking meetings, closes business. You are wrong. Your employer is wrong. You don’t need a phone number, email address, or intro, and you don’t need a meeting, catch up with how the internet is changing everything, and start creating value.

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Paul O'Brien
Paul O'Brien

Written by Paul O'Brien

CEO of MediaTech Ventures, CMO to #VC, #Startup Advisor. I get you funded. Father, marketer, author, #Austin. @seobrien & @AccelerateTexas. https://seobrien.com

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