Stop Pitching, Start Storytelling


My Storytelling Framework For Winning Deals

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The best sellers don’t just pitch. They tell a story.

'But, but, Jesse... they didn't cover storytelling in my sales enablement training!!! Besides, Marketing owns our brand narrative, so I'm all set...'

Right. In my experience, it's 100% correct that storytelling is usually glossed over in sales enablement training.

But when it comes to getting results, a true Sales Player NEVER relies on marketing's approved brand narrative alone (sorry marketing).

Sure, it's a starting point, but come on, when was the last time your marketing team carried a revenue quota? Presented to a panel of IT buyers? Enabled a champion to present a business case to their C-level leadership?

Probably never...

YOU are responsible for how you present your solution, and the story around it to your buyers.

Oh, and if you happen to sell for an early startup, there's a pretty good chance you don't even have a marketing-made narrative framework to begin with, since most early startups are constantly changing and pivoting. Storytelling is a survival skill for early GTM hires.

So, how might an ambitious Sales Player like yourself improve their storytelling ability in order to develop a stronger point of view for customer conversations?

Don't worry, Old Uncle Jesse has got you covered...


My Storytelling Framework:

A few years back, a mentor of mine shared Andy Raskin's write-up called The Greatest Sales Deck I've Ever Seen. To this day, I still reference it often to be sure I'm following the elements he outlines in the article.

Over the years, I've implemented Andy's suggestions in my own pitch narrative, and for the rest of this post, I'll be breaking down:

  • How you can begin to craft your own pitch narrative
  • The specific changes I've made to Andy's template to make it my own
  • How I combine Andy's ideas with Simon Sinek’s Start With Why for even stronger impact

There is a lot to cover on this topic, and it is very much an art form. I could probably write an entire book on this (maybe I will...), but for now, let's start with developing a story for your first meeting with a brand new prospect.

To show a real-world example, I'll use the pitch deck from my days as a Founding AE.

The Why Slide: Make a Bold, Polarizing Statement That Resonates With Your Buyer Persona:

Engineering performance shouldn't be a black box. Do you agree Mr. or Mrs. DevOps Leader?

By the way, it's totally okay if your prospect doesn't agree. It's an opportunity to find out why they don't agree and if they won't ever agree you can just end the call since they likely aren't ready to buy from you.

If they do agree, cool, which of the bullets listed resonate most?

  • You've now drawn a clear line in the sand and your prospect is beginning to see things from your worldview.
  • You've gotten your first yes. (Just a few more yeses and you'll have a signature).
  • You've started a two-way conversation about which pain points matter most and you can now focus on mapping your solution to those pain points.

The How Slide(s): Begin Building The Case for How Your Solution Can Help Solve Their Biggest Challenges and Make Their Wildest Dreams Come True:

This part of the story is all about beginning the process of mapping your solution to their pain points by defining The How. You can also think of this as the premise that will support your final conclusion.

You already have activity data in your delivery systems; here's how that activity data could be turned into valuable performance management insights without changing your current process.

This is also your first opportunity to showcase how you differentiate from others in the market and how you're 10x better than the competition.

Now that your prospect understands why you exist, how you're different, and how you can help them, it's time to drop the mic!

The What Slide: Close With a Strong Conclusion and Leave Them Wanting More:

This is the final part of your pitch story. Your goal now is leaving them wanting more and getting next steps.

I've found that a great way to close out is to bring it back to the high-level and call out what they are getting with your solution.

A few other What questions you can deploy here are:

  • What happens if you do nothing about this?
  • What's in it for you if we can help solve this?
  • What is the process for fully evaluating this?
  • What's your ideal timeline for solving this?

TLDR:
Storytelling isn’t a nice-to-have. It’s a survival skill required to win large, complex deals and something that separates okay reps from great ones.

The above breakdown is only the jumping-off point for how you, as a Sales Player, can unlock the power of storytelling in your deals.

Want to work with me 1:1 to develop a powerful pitch story for your deals? Schedule your FREE intro call here

Until next week.

-Jesse


Featured Episode: What Top Tech Sales Candidates Do Differently

The best candidates don’t just show up, they sell themselves at every step. In this episode, Jesse shares the high-leverage interview plays that get offers in today’s brutal job market.


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Sales Players is on a mission to reach 1,000 reps, founders, and operators in tech with FREE weekly content that explores the mindset, skills, trends, and tools used by the industry's top players to win at the game of tech sales.

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