Account Executive

April 15, 2022

Hypothesis Prospecting: How to Personalize Cold Outreach at Scale

Hypothesis Prospecting

It’s a mouthful, but way easier than it sounds.

“Well It SOUNDS like I’m heading back to science class reading this nonsense.” - you (probably).

Ouch...but fair. Let’s remove the scary teeth & replace ‘em with those fake Halloween fangs.

We know sales is a science. But let’s make it more enjoyable: Bill freakin’ Nye style.

By the end, you’ll be shouting the theme song we know & love along with me (Bill, Bill, Bill!)

The Problem

Every hero’s journey starts with a big problem. Since you’re the hero in this one, here’s the issue:

Cold outreach needs to connect with your prospect personally.

In order to get a response & kickstart the sales cycle, you need to show up with relevant, targeted & timely messaging.

More often than not, you’re scraping the bottom of the CrunchBase barrel to find something your prospect MIGHT care about. Probably goes something like: “Noticed you raised some money, can you buy my tool & help me hit quota? I need this.”

The truth is: buyers care about themselves. “How is this going to help ME?”

Enter: Hypothesis Prospecting. (or Hypothesis Selling. Same-same.)

What is Hypothesis Prospecting?

Just like 5th-grade science: a theory you’re testing = a hypothesis.

“I believe throwing a paper airplane at my teacher will lead to a principal’s office trip.” Let’s test it!

It’s a similar idea to prospecting in sales. You form a theory around what your prospect might have a problem with based on company & personal research.

To test that hypothesis, reach out to the buyer with your suspicions & ask “am I in the ballpark?”

If you find the right spot or hit a nerve, you have a 99.97%* shot at getting a response. (Science is never 100%, *results may vary).

Either “Yes. You nailed it. Tell me more.” or “No. I’m not. But great outreach.”

It’s a win-win. Especially if your goal is to just get a response. Best case: a targeted conversation.

How it Works

Sometimes prospect research just fails you:

  • No noticeable buying signals. No recent funding rounds, partnerships, etc.
  • Their LinkedIn page hasn’t been updated since landing their first post-college job.
  • Facebook/Insta doesn’t show off the Middle Earth map bed they display their Lord or the Rings obsession with.
Hypothesis Prospecting Problems

Can’t find an obvious prospect need? It’s time to hypothesize.

Take the small bits of info available and start guesstimating about their life/pains/problems:

  • Are they a part of a startup? Scale-up? Series D Goliath? or Ma & Pa shop?
  • Does their department have 15 new people or 3 seasoned vets?
  • Who do they report up or manage down to?
  • Any recent hires starting to onboard?

All fantastic starting points to formulate that hypothesis.

Let’s see it in action:

“My guess is you after being an Account Exec for a few years, you’re looking for ways to spice prospecting up a bit. You landed on this page cause someone sent you a link or you’ve heard about hypothesis prospecting before. You’re looking to learn a bit more & take away some actionable examples. Am I in the ballpark?”

See what I did there? Made an assumption about what you might be looking to accomplish & reached out to start a convo.

Here’s another version just for kicks:

“Love that you're taking the time to read this article. You’re probably looking to take advantage of your network and the content they put out. Have you considered messaging the content creators directly? I bet they have additional insight and can really help you apply this to your industry/product/vertical.” (Seriously though...feel free. We love helping sales pros crush it.)

I can write this stuff all day.

The Formula

Research + Persona/Role/Position + Product = Hypothesis Selling

  • Research: what you can find.
  • Persona/Role/Position: what you know about their world.
  • Product: how you make their world better.

With this basis in mind, it’s time to deploy.

Take everything you can find, combine it with what you know, and start hypothesizing about EVERYTHING.

Seriously...get obsessed!

Some Hypothesis Examples (Generic AF)

”The car in front of me is slowing down, but there isn’t traffic, my guess is they are texting.”

  • Pass them, and boom, they’re texting.

“Every day at 3:30 pm, the ice cream truck is within hearing distance. The baseball field is also within hearing distance. My guess is he drives by the park at the same time daily because there is a baseball game. I wonder if his company is hiring for summer-seasonal work?”

  • Not for you. But for your lazy bro-in-law.

“My prospect accepted my LinkedIn request. It’s likely that they’ve seen my emails/cold calls and know that I’ve been reaching out. My guess is they liked my approach, but the timing is probably off.”

  • Time to reach out via LinkedIn with your hypothesis.

“The pet store put up signs saying you can now schedule an in-person meeting with an expert before purchasing a pet. Their website doesn’t have any booking software. My guess is the person scheduling all the meetings is overwhelmed trying to keep track of employee schedules and meeting time slots. There must be a ridiculous spreadsheet, a notebook or even worse meetings are being missed.”

  • Is an in-person pet expert meeting a real thing?? This might be a gold idea. Someone give this a go and get back to me.

So why should I try Hypothesis Prospecting today?

The purpose behind it is two-fold:

  1. Show your prospect you know what you’re talking about & can empathize.
  2. Start a conversation. Doesn’t have to lead anywhere. But a relationship is never a bad thing.

It’s about presenting a value-add in a credible way & invites them to meet you halfway.

While it may not be smooth at first, like all things: practice makes perfect.

Truly trying to understand your prospect's world and where you could add value is the recipe for success in any sale.

So get scientific and go full-blown Bill Nye. Put on the science jacket and start hypothesis selling.

Bill didn’t disappoint when your teacher pulled in the TV, he won’t disappoint now (trust me).

Always remember: you’re just trying to start a conversation, not pitch. There’s a science to it.

Bonus: Some successful examples I’ve written

Hypothesis Prospecting Example #1
Cold Email
Hypothesis Prospecting Example #2
LinkedIn Message
Hypothesis Prospecting Example #3
LinkedIn Message
Hypothesis Prospecting Example #4
Cold Email
Hypothesis Prospecting Example #5
LinkedIn Message

You'll like these emails 🥒

Pickle writes to their friends every few weeks with spicy tips to make their wall-to-wall meetings suck less.
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