Seven HUGE Lessons on B2B Sales from Pitch Anything’s Oren Klaff

Oren Klaff is the author of the classic bestseller on the science of persuasion and getting the deal done, Pitch Anything: An Innovative Method for Presenting, Persuading and Winning the Deal. Since its release in 2011 it has been considered by many to be the sales bible and it’s one of the books I have recommended the most to fellow entrepreneurs, sales professionals and people who just want to get better at, well, persuasion, having first read it when embarking upon my own entrepreneurial journey back in 2012.

Unlike most of the books on my overflowing bookcase, I return to Pitch Anything often.

Today, Oren is the Director of Capital Markets at investment bank Intersection Capital and founder of Pitch Anything. Oren has applied his neuroscience-based approach to capital raising to secure over $2BN from high net-worth individuals and financial institutions for entrepreneurs.

After learning about Oren’s extensively mind boggling collection of motorcycles and cars, we delved into the nitty gritty of doing deals, and it was an opportunity to ask questions based on my own first hand experiences, particularly when it comes to B2B sales and selling to large enterprise.

I’ve captured seven of the many key lessons I personally took from my conversation with Oren. You’ll find a hell of a lot more by listening to the entire conversation on Future Squared when it goes live on September 8, and can find a number of resources at the bottom of this post to explore further.

With that, I bring you, seven big lessons on B2B sales from my conversation with Oren Klaff.

1: How to sell to large organisations who like to drag their feet

The Situation: So you’re selling a SaaS product and you’ve had a handful of meetings with a large enterprise prospect who insists on engaging multiple stakeholders and committee meetings, constantly changes the scope, says things like “Oh, Mr. X is out of town so we’ll need to push our next meeting back four weeks” and says that, “if this all checks out we’ll have to move to RFP”.

You probably don’t have the time, resources nor the patience to play this game.

The Resolution: You might respond with something like: “Yeah, we’re not gonna do that. Listen, we’ve had two phone calls and two meetings so far, we’ve spent almost eight hours on this, four people from your side, four from mine, I don’t know about you guys but our man hours are $1,000 fully loaded. I’d like to think you’re the same. Collectively, we’ve spent about $15,000 and we have no idea what to do? If so, then this doesn’t make sense to me. We understand what you do, how to help, how long it will take, what our margins will be, the ROI it will deliver for you, so what’s the problem? Why don’t we do this? Unless you say to me that we have legitimately spent $15,000 on this and we have no idea what to do. Otherwise, let’s go away, store our names on each other’s Rolodex and maybe some time in the future we’ll work together, who knows. If on the other hand that’s not the case, then tell me now otherwise we’ve got other companies to speak with who are serious about getting a deal done.”

2: Getting past people’s fear of uncertainty and of the unfamiliar

The Situation: People like shiny new things, but when push comes to shove, decision makers tend to succumb to biological evolution and make what appears to be the safest decision. If you’re selling something new and novel such as a blockchain based platform, it might be challenging getting passed your prospect’s fear of the unknown and novel.

The Resolution: Lead with what’s familiar. Rather than coming out and saying that you’re a blockchain based platform that does X, lead with what your prospect already knows and is comfortable with. Speak their language. Mention the projected ROI, the value that’s being delivered and for who, the regulation it complies with, and any other important factors… then and only then, once you’ve instilled confidence in your prospect, introduce the fact that, “oh and by the way, it’s hosted on the blockchain!”

3: How to regain composure when you’re lost

The Situation: You might read many book on sales or persuasion, but as Mike Tyson once said, “everybody has a plan until they get punched in the face”.

The Resolution: Lead with simple facts. In such situations, Oren advises to simply state the facts you can never forget. “Hey guys, I’m totally lost. As I understand it this is the problem you have, we have the solution, it costs X, the projected ROI is Y, we can deliver it tomorrow, your people can start using it immediately, you’ll start seeing measurable benefit next week and the risks have all been mitigated to an acceptable level. So what’s the problem?”

4: How to use the moral authority frame

The Situation: You’re selling to an organisation who says they’re all about being innovative and working with emerging companies on their website, but the reality is far from the facade.

The Resolution: Say something along the lines of “I’m confused. Your website says one thing — that you’re a startup friendly, fast moving organisation — yet you’ve taken over three months to make a decision. This isn’t how you work with startups. Startups don’t have the time or resources to do this. Are you truly the progressive innovative firm you purport to be or not? Because if it’s a fabrication, then I’d be more than happy to go our separate ways and stop wasting each other’s time right now.”

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5: Building rapport

Situation: Sales executives usually spend time at the start of a conversation looking to find things in common and making small-talk about politics, sports, weather and vacations. It is said to help the sales exec come across like more of a person than an executives, because, after all, people buy from people they like. However, Oren suggest that this thinking is flawed.

Resolution: Instead, focus on social context. “I noticed that you guys did Project X at Microsoft, I know Rameet who was in business development — he and I went to Stanford together. Did you guy get a chance to work with him?” That’s social context and that’s important and relevant. Photos of your kids playing Marco Polo in the Bahamas, not so much.

Oren says something quite contrarian to conventional wisdom; “rapport isn’t something you create at the beginning of the conversation, it’s something you’ve earned by the end of it.”

6: Never give up social status

Situation: More often than not, if you’re a startup pitching for capital or a sales executive trying to secure a deal, you might find yourself saying something along the lines of the following:

“Great to meet you, thanks for your time, we’re really delighted to be here and have the opportunity to present.”

When you’re needy, you diminish yourself, says Oren. And not only that, but it makes prospects feel powerful. And when they feel powerful they have the following physiological reactions.

1 — their vision narrows and they don’t see your ‘full scope’

2 — they see things at a cursory level and don’t appreciate your depth

3 — they are willing to take more risks like surf the web or look at their smartphones while you’re trying to present

Resolution: Be the prize. Don’t give up social status.

Building on #5 and not giving up social status…

7: Beating large companies to the deal

Situation: Your boutique capital raising firm is pitching for a deal and you know that huge behemoths are also throwing their hat in the ring. However, you also know that for huge behemoths, the deal isn’t a big one, but for your boutique firm, it’s massive. Your prospect says something along the lines of “well, you know, we’re talking to Goldman Sachs as well”.

Resolution: “Great, you want your wife to be impressed, to tell your friends?I’ll tell you this, you’re a $30 million deal. At Goldman Sachs it would be punishment for some interns to work on your deal. Who at Goldman Sachs is excited by a $30M deal? The Managing Director, VPs? No way. They’ll say “I got stuck on this tiny deal”. But if you want the comfort of that logo, great. Go for it. But if you want the A-team, a team for which $30M is a big deal, then that’s us. $30M is our sweet spot. If you want the A-team, we’re right here, but just tell me what you want and I’ll help you get it.”

These lessons barely scratched the surface of what we discussed in our hour long conversation. To avoid missing out on our conversation, subscribe to Future Squared on Apple Podcasts, Google Play, Spotify or wherever you listen to podcasts and tap into past conversations with thought leaders across myriad of areas such as Kevin Kelly, Grant Cardone, Adam Grant, Gretchen Rubin, Rand Fishkin, Neil Patel, Steve Blank and many, many more.

Oren Klaff Resources

Get the book: Pitch Anything on Amazon
Online Course:
Twitter: @PitchAnything
September 1, 2018




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