Bootstrapped Giants

My guide to a 10/10 sales meeting

Published about 2 months ago • 5 min read

A Bootstrapped B2B business hasn't really started until it has its first customer.

Until then, the business is just an idea or a product. That first paying customer is everything.

A few weeks ago, I introduced you to MMM, Meetings are the only Metric that Matters.

"Ok Jesse," I hear you thinking. "I am getting a few meetings.

How do I RUN the perfect meeting, one that’s bound to lead to that special moment: my first paying customer."

Here’s how I do it:

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Let's get into each of my prep elements.

1) Deck

While I try not to use it much, having 5-10 slides that outline the story, business and offering is important.

As you'll see below, having visuals keeps your message clear.

(Hit reply and tell me if you think I should write more about preparing a deck, along with examples from GrowthAssistant and Kahani.)

2) Offer

This is critical. I have a very salient, specific offer.

Services businesses especially mess this up by not being ready with clear pricing.

Prospects want to know "How much does it cost? What do I get for that cost? For how long?"

The simpler and clearer you are, the better it is for them.

When we launched GrowthAssistant, a lot of our success came from simplicity: $3000 a month for a full-time, high-quality global marketing person.

That’s it.

3) Research

Insane dossiers are my thing, but you should at least have basics: LinkedIn info, a list of mutual connections, an understanding of where they used to work, etc.

Don’t go in cold.

Here’s my rough agenda for a 30-minute meeting. (Do not make your first meeting longer.):

  • Small Talk + Magic Question: 1-2 mins
  • Their Story: 2 mins
  • Your Story: 5 mins
  • Show don’t Tell: 5 mins
  • Q&A: 5 mins
  • Discovery: 5 mins
  • Next Steps/HW: 5 mins

Let’s dive in:

Small talk is straightforward. These days it's “Where are you?” or something like that.

If you got the meeting through a friend, talking about how you both know that person is a great way to start.

A lot of sales meetings start with the prospect being closed off, so any way you can quickly build and grow trust matters.

I have two magic questions that I love:

1. What led you to take this meeting? Or the variant: Why were you excited to take this meeting?
This is my favorite because usually, the person starts selling your product/service back to you.
For Aux, we regularly hear Private Equity folks saying:
“Well we look at a lot of deals where digital marketing is a critical component but we don’t have a go-to partner to help us evaluate them, so when we heard what you do, we wanted to meet.”
There’s something about them naming why this could be important/matters that seems to start everything off in a positive direction.
2. What would make this time together a 10/10?
This second question prompts them to share what they want and gives you the chance to deliver it.
Usually, if someone says what they want and you deliver it, you gain their trust, which is the key to any business relationship.

My third question is: “I’d love to learn more about you, your company, and your role.”

It lets me hear from them and also sets me up to go into my pitch later.

This allows me to hear what matters, what’s important to them, and any important context.

An important sidebar:

Notice how from the start of the meeting, I am in control. Nothing is more painful than a meeting where it's not clear who is driving, especially in a sales conversation. Your prospect wants structure and guidance.

Oftentimes, I will go through the agenda to start the meeting or after my "10/10" question.

E.g., “What I’d love to do is hear what had you take the call, a few minutes on your background.

Then I’ll share my story and our offering. Then we can go into the next steps. Does that work?”

It makes someone less tense because they now know what to expect. It builds trust. (You’ll keep hearing bring up the need to build trust.)


People want to buy from people – and “founders” are sexy.

I’ve never sold anything without talking about myself a little bit and sharing the “idea” or insight for the business, along with how we got started.

For GrowthAssistant, it sounds like:

“I’m Jesse, a serial entrepreneur. My first company, Ampush pioneered paid social, back in 2010. We helped companies like Uber, Dollar Shave Club and Peloton build their growth engines. While building that company, I built a global team that helped with lots of rote – but important – tasks, like reporting, creative iteration and influencer outreach. After we sold the company, a lot of my former employees started running growth at brands. They kept calling and asking where they could get a global team. I looked around and didn’t find anything. That’s when I decided to start GrowthAssistant.”

From that story, everyone is engaged, nodding, and it all makes sense.

After that, the conversation flows naturally into WHAT IS IT and the OFFER.

One pro tip for improving: if you keep getting the same questions after your pitch, integrate those into the explanation part of your story.

After telling my story and presenting the OFFER, I immediately move to SHOW vs Tell.

Almost all my pitches have some kind of demo. I have browser tabs opened and I’m ready to show something.

In the case of Ampush, I’d pull up client creative examples and landing pages.

In the case of Aux, we show anonymized deck examples for previous clients.

For GrowthAssistant, I pull up my own Slack and show how I USE GrowthAssistants in my own businesses.

This is how I show:

Whatever you do, SHOW SOMETHING!

If you tell a good story and show some great stuff… it will naturally lead to:

At this point, the person will start asking questions: How long does it take to set up? How long is the normal engagement? What do you charge for X? How does ABC work?

These questions are a CRITICAL signal that you’ve actually unlocked interest. If you finish and get crickets, it's not a good sign.

Now, after the person has asked questions… it's your turn to do some discovery.

Questions you ask differ based on your business. There are tons of discovery frameworks out there… I like the MEDDIC one:

It helps answer key questions like, What's their issue? Who will make this decision? What’s needed to finalize it?

Last, but not least: nail the next steps and even book the next meeting. This depends on your sales process.

At Aux, we ask the PE firm for a homework assignment, where we’ll do a little work on one of their portfolio companies.

At GrowthAssistant, we confirm the job requirements.

And then ideally, we say, let’s chat in 1-2 weeks - “Same time next week work for you?” (the BEST line!) because it starts the scheduling process.

The other reason I like to force this is if they hesitate or say "no," it gives us an opportunity to say: “What concerns do you have?” and then the real talk begins.

At a minimum, you get some feedback. At best, you can address the concern or know what to address next time.

Or if they really aren’t the right fit or aren't interested, you can spend your time more productively elsewhere.

Regardless, it helps you learn which is the most important part of sales (and entrepreneurship.)

Close out the meeting, and ensure you send the follow-up right after.

(For speed, I usually have a prewritten template. I fill in the blanks and send it.)

And add the person on LinkedIn.

There you have it! My insider's guide to running a great meeting.

I promise, that if you follow this along with MMM, and keep learning/iterating, you will see your business compound.

Have a great week!


Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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