The Best Sales Advice I’ve Ever Received? “Go In As a Buyer.”

 In Cutting Through

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I want to start this post by saying that I do not personally endorse the actual tactics or sales pitches described below. I believe that simply being aware of this idea and the psychology behind it – going in as a buyer – and hearing the following two examples can encourage sales leaders to think outside the box and get more creative with their pitch to cut through the noise.

Where it started

A few years ago, I became obsessed with Wiley Cerilli, whom I still consider a sales genius.

It all started after I stumbled across this video:

The reasons I find the video fascinating (and think the guy is a genius and total beast):

  • The guy actually did true customer discovery for Single Platform (and investor discovery, for that matter) at every step. He presented a pitch to investors and watched their facial expressions. Then he updated pages until he had a pitch that was good enough to raise capital.
  • He pre-sold a product that didn’t exist (Single Platform) to restaurants until they were handing him checks, then he’d say he didn’t have it yet but it’s coming.
  • When building the initial sales model, he optimized metrics for his series A pitch deck. This was mainly for time to payback for a salesperson.
  • When out raising a subsequent round, they got acquired for $100mm.

However, the most genius thing of all in my opinion is number 7 in this blog post that came from an interview with him:

“Adopt a ‘buyer’s mentality.’

At Seamless, the sales team was struggling.

Their tactics simply weren’t working, and Cerilli realized they needed to rethink their approach. What did they have going for them?

They had many pre-formed relationships with big companies that used the platform to regularly order food. ‘When you go in with a seller’s mentality, you say things like, ‘Hey, it would be great if you signed up for Seamless. It would be awesome for you because of all these things…,’’ he says.

When you go in with a buyer’s mentality, you say, ‘Hi, we manage the food ordering for Goldman Sachs, and we’re considering adding your restaurant to our system. We have some questions for you, so how about we set up a meeting?’”

That. Is. F’n. Genius.

Cutting through

Instead of being one of a million cold callers hitting small business up (like we did for many years — it’s painful, they don’t want to hear from you), the guy was saying he was with Goldman Sachs and wanted to set up a corporate account.

What restaurant in New York doesn’t want that?  

Single Platform: a legendary pitch (with questionable ethics)

After I finished my virtual stalk of this dude and devoured every piece of content he ever produced, I wanted to know exactly how he got Single Platform from $0 to $100mm in 18 months.

I could see how you could get this to work well for one side of a multi-sided marketplace business. But I still couldn’t see how you’d get it working for a straight SaaS product.

He’d just done that, and I wanted to do it for Robly, if I could.

So to find out, I pulled a move I do frequently when I’m looking for information.

I started pinging every high up person in his organization to ask if they wanted to meet to chat.

Usually I keep it casual, like I’m wanting to meet leaders and entrepreneurs in the city. But there are undertones of the possibility of potential roles, advisor or senior employees.

I ended up having some extensive conversations with a former employee who was there for years and a rock-star in their sales organization. My my mind was blown.

You’ve GOT to be kidding me: 10% demo booking rate, ON AVERAGE?

The intel I got from the former employee was that they were buying restaurant leads from info.usa and booking demos at a 10% rate.

There is simply NO WAY that you can go in as a seller and book demos like that.

You’ll get 2% if you’re lucky, and the data is good. I knew from experience.

So what were they doing?

I had to know.

Deceptive but effective foot-in-the-door tactic

From my years of building sales organizations, I know for a fact that the purpose of the cold call is to book a demo.

The closer doesn’t care what the prospector says, so long as the prospect shows up, and is qualified to buy.

We learned that the more excitement you can generate the more likely you will be able to get your foot in the door to pitch.

What I learned from Wiley Cerilli was if it doesn’t seem like you’re selling at all, but instead giving the prospect something they want, and want badly, there is a much higher chance they will listen to you and show up for the demo.

Before I go into how this 10% conversion prospecting pitch went, I’ll briefly describe their  product at the time.

Single Platform was the only way restaurants could get their menus onto a handful of the largest online directories: Trip Advisor, Google, Yelp, etc.

A useful product.

So, while you’re reading this, keep in mind that Single Platform was technically partners with these organizations.

The pitch (more or less)

I have no idea if this sales pitch is still in use, nor do I care.

This is for purposes of illustration only, to give another example of how you might go in as the buyer, in a situation where it seems to do that: a SaaS product that posts menus online.

“Trip Advisor has partnered with our company to interview [insert something like “three Mexican restaurants in the East Village”] and pick one for a feature piece on their website. We’d like to give you a short, 20 minute interview tomorrow. We’re also speaking to [competitor A and competitor B]. When would be a good time to call back for the interview?”

I’m not getting the verbiage exactly right, but that was the essence of it. You can read some discussion about it online here.

The restaurant owner, instead of hearing some canned pitch about something they don’t need that we are all programmed to hang up on, was being offered free publicity.

There was also another hidden psychological element at play.

The restaurant owners, instead of showing up for a pitch with their guard up, were showing up for an interview to basically audition for Single Platform (or TripAdvisor), rather than the other way around.

Single Platform then got them on a very high pressure sales demo, somehow flipped the script from interview for TripAdvisor to, “we’ve got this thing that allows you to post your menu everywhere and we’re the only ones who can do it.”

All that I find impossible (yet encouraging) about this pitch

  1. First, it’s impossible for me to believe they had the ability to gracefully flip this script from “we’re interviewing you for TripAdvisor,” to “This is Single Platform, you need it, and we’re the only way you can get it.”

    But, they could, and they did.

    Knowing this made me try to think harder and more outside the box about our sales process.
    It pushed me to try to step outside of myself. I examined whether or not I was accepting things as impossible that were actually lazy thinking and old-school beliefs.
  2. They got an average of 10% demos on 100 cold, purchased leads a day.

    This is an INSANE stat for prospecting, and I confirmed it in multiple spots. If you’re running an outbound business, this will make you lick your chops and try to figure out how to make it work for you.
  3. They made the unit economics and cash flow of a NYC cold calling operation work at a $500 annual contract value (ACV) price point.

    Common knowledge (well, at least based on Jason Lemkin’s musings) suggests that anything below $300 per month won’t work for outbound.

    Low-touch inbound can work at $99/month, but in and around $50/month, forget it.

    But that’s because no one on God’s green earth realizes that it is even possible to convert 10% cold leads into demos.

But Wiley Cerilli proved that it is indeed possible.  

How I’ve gone in as the buyer

We want to work with influencers. I want to align our brand with the most elite “athletes” of digital marketing.

I realize that these “athletes” are all so rich that they probably aren’t optimizing for cash anymore. But, people love equity.

My view is that if you can part with a little early in the game, it goes to the right guy, and your name gets out there, that it’s a fantastic exchange for both parties and can lead to some real parabolic growth.

The Pat Flynn/ConvertKit situation is an example of a success story. Pat not only took him on as an affiliate, he got an advisor equity stake.  

These influencers are also potential customers. So it helps us get them on product demos because more eyes on the software is better.

So I used Wiley’s “go in as the buyer” idea as a part of our influencer strategy.

I hired a beautiful, articulate British model named Alice Phillips. I had her send a video message via Instagram to a list of our top candidates saying we were looking for ambassadors (which we were). And, we were willing to give equity in exchange for passively promoting our product.

Here’s the video:

It was followed by a series of “check your DMs.”

The response rate was fantastic, and we are currently in active communication with some big names.

How else can you go in as the buyer?

This is a genius move by AirBnB, who famously went in as the buyer to people listing on Craigslist. More about it here.

AirBnB targeted Craigslist listings in a similar way.

They offered something the people with the listings wanted: free additional exposure, like the TripAdvisor example above.

I’m captivated by this idea. And with a 10% conversion rate on cold leads into demos on purchased data, you can make almost ANY outbound sales model work.

I’d love to hear other ways sales leaders have “gone in as the buyer.” Share your stories in the comments!

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