How to sell to uber-successful people
I’ve had the chance to sell to some wildly successful businesspeople over the years, from Sir Philip Green (former chairman of Arcadia group) to Rupert Murdoch (executive chairman of NewsCorp) to Kris Jenner (CEO of the Kardashian family empire) and many others in between.
I’ve learned 3 things from those experiences:
Get to the point quickly
Reference their competition to drive urgency
Use data to overcome objections
Get to the point quickly
While the uber-successful are usually uber-rich, their most precious asset is not their money. It’s their time. You need to get to the point quickly and answer the #1 question on their minds—What’s in it for me? I remember learning this the first time I met Rupert Murdoch when I worked at Fox Interactive.
I was there to pitch him to on funding the ad targeting platform I was building, which at the time was the first of its kind in the industry. “You’ve got 15 minutes with him, so don’t waste his time”, our division president told me.
However, I’d been heads down in the details of the product for a few months so I instinctively fired up the demo and started jabbering on about big data, algorithms and machine learning.
5 minutes into the meeting he cut me short and said, “The engineers you need to develop this are expensive, right?”. “Um, yeah” I replied, “There are very few engineers available who can put the theory into practice at the scale we have.”
“But you can charge a premium for the ads, cant you?”, he continued, “How much?”. “2-3x” I replied.
“Great. Carry on”. he said and got up and left for his next meeting.
I remember being amazed at how quickly he’d been able to simplify a complicated idea, tie it to the business outcome that he cared most about and make a decision. It’s a lesson that has stuck with me ever since.
Reference their competition to drive urgency
Wildly successful people are without exception wildly competitive people. They watch their competitors like hawks, are obsessed with figuring out how to gain an edge over them and are heavily influenced by competitor insights.
I learned early in my startup career the power of using competitive insights to create scarcity and overcome the power imbalance of being a startup selling to a big corporation. I’ve used this strategy in hundreds of sales calls over the years but one that always sticks out was with Sir Philip Green, the billionaire former chairman of the Arcadia Group apparel empire. I was there to pitch him on advertising on Polyvore, which at the time was the leading social network for fashion brands.
My head of sales and I sat down with him across a conference table the size of a New York apartment, clearly designed to intimidate vendors, so I could tell the tone of the meeting was going to be confrontational. Sure enough, I got one slide into our deck when he said, “Look, cut the bullshit. If I gave you $1M, how much can you make me?”. (Note how he also got straight to the point).
I said, “Honestly, if you gave me $1M, we wouldn’t be able to spend it for you because we aren’t big enough. But if you gave us $100k, we could generate you $500k in sales”.
He said, “Well, I appreciate the honesty. It makes you more credible than most of your lot. But $500k??!! If I’m doing advertising I need to see at least a 10:1 return, or I’m losing money!”
I replied, “Well, all the high-street retailers are trying to acquire online customers, as well as all the venture-backed pure-plays, so it’s very competitive. Most people are working on a 4:1 return and optimizing for new customers rather than instant profitability. If you want us to run you at 10:1, I’m afraid you won’t get much of a look in.”
The tone of the meeting instantly changed. He started asking questions about how the product worked, how soon we could launch and how long it would take to see results—all classic buying signals. We wrapped the meeting and a couple of weeks later my head of sales received an order for $100k.
Use data to overcome objections
If there’s one thing I’ve learned about selling to uber-successful people it’s that, unless they consider you a peer, the odds of persuading them with your words and opinions are very low. However, once you replace your opinions with your data, not only do you level the playing field, you can actually tilt it in your favor.
I’ve used this approach countless times over the years, but one of the most memorable ones was the time I did a QBR with Kris Jenner when I was CEO of Adly, a Twitter influencer marketing agency. Just like Rupert and Sir Philip, no sooner had we sat down in her office, she launched straight into it and demanded that we pay her clients (aka her children) more money (+1 for getting straight to the point). She even threw a bunch of data at me, saying that “everyone” was offering her clients 5-10x more per sponsored tweet than we were.
As a startup we couldn’t afford to pay more, so I had no choice but to figure out how to overcome the objection. Fortunately, I’d taken a negotiation training course early in my career, where I’d learned that one of the best ways to do this is by acknowledging it (aka mirroring) and then asking clarifying questions—so I asked her a series of questions that established that while “everyone” was throwing money at her, nobody was coming back with repeat business.
I then introduced my own data to reframe the conversation and tilt the playing field in my favor. I showed her a printout of how much we had paid her clients each month for the prior six months, an amount that was already over $200k and growing each month. It was incredible how her tone instantly changed from confrontational to collaborative as she stopped focusing on price and started asking how we could do more business together.
Going through that experience with Kris really crystalized for me the power of using data to overcome objections and has become a cornerstone of how I’ve approached sales ever since.
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