Why my salespeople close more deals

This month, we’re launching Bootstrapped Giants’ first product: my B2B Sales Blueprint.

So in today’s newsletter share the sales fundamentals that I learned early on and CONTINUE to teach my sales teams.

In my first month at McKinsey, another new analyst and I were assigned "client interviews.”

This is where you have to call various employees of the client and ask a bunch of questions to try and understand why something is going wrong at the company.

This other analyst had graduated from a "college in Cambridge" and was whip-smart.  But within a week, I had done 20 interviews and he had only done 2. 

The partner on the project was blown away by my speed and insights.

To me, it was just another sales job.

"How did you get SO good at sales, Jesse?" the partner asked me.

That’s the same question I’m asked by salespeople at my venture studio’s companies and by many newsletter readers.

The partner wouldn't take “I don’t know” for an answer.  So I dug deep and found AN ANSWER.

What people consider my "natural" sales ability comes down to two very early life experiences:

1. Shoveling snow with my brother

2. Doing Speech & Debate in school

And today, I’m going to use these two formative experiences to go a level deeper on how to "improve" your selling.

EVERYTHING is sales. Bootstrapping means selling to your customers, employees and suppliers. 

Investors sell money to entrepreneurs. Entrepreneurs sell themselves to investors.

Even employee retention is SALES - you convince a person to keep coming back to work for you, despite other job or entrepreneurial options.

What is sales, though?  I like to call it "Persuasive Communication," and it’s the top skill all leaders should cultivate.

These are some fundamental sales skills that I learned from selling with my brother and from doing speech & debate in school.

If I ran “Jesse’s sales bootcamp,” the first thing I’d say is, "Just make 50 sales calls."  My brother and I did this door-to-door at age 10 after snowstorms, where we sold snow-shoveling services. 

Then, at age 17, we did it at our telemarketing job, where we sold extended warranties for HP service contracts.

What both of those experiences have in common: TONS OF REPS.  And nothing makes you a better seller (or a better anything) than tons of practice.

All the best entrepreneurs I know do that to figure out a new market or idea. They just “work the phones.”

One of the hardest parts of selling is how nervous it makes people feel. 

Once you make 30+ calls, I guarantee you that you will not feel nervous anymore.

There are 2 main reasons people get nervous when they’re selling:

1. They feel like EACH CALL IS MAKE OR BREAK!  It’s a judgment on them, their baby and their lives.

2. They are afraid of what the other person thinks of them or, as Conscious Leadership Group calls it, "They take responsibility for how others feel/view them."

30+ calls in, and you’ll no longer be dealing with reason #1. 

You’ll be like a baseball player who cares more about their batting average than a single at-bat. Doing 30 calls will show you that.

And your prospects’ responses will clear reason #2.

You’ll notice that the same script has a huge distribution of reactions… so you must not be making anyone feel anything — that must be their own doing.

Sidebar: Nick Pujji, my older brother, is the youngest equity partner at Dentons LLP, the largest law firm in the world.  The reason?  They've ”never seen such a young partner be so prolific in growing his book of business.”  His favorite quote about sales?  "It’s like digging for gold: would you pay attention to the dirt, or just move it to the side so you can find gold?"

There is no substitute for practice.  Practice opens up two more opportunities: feedback and narrative.

In our snow-shoveling days, between knocking on doors, my brother and I would rapidly reflect.  If we made the sale, we’d ask “Why?” If we didn't, “Why not?”

He would tell me I asked too many questions.  I would tell him his energy was off. 

Well, by the 10th pitch, if we improved 5% each time… we were 70+% better!

So it wasn't just practice, it was also keeping lots of space for feedback and improvement.

I think this works super well with a partner of sorts, where you can give each other tons of feedback and share what's working and what's not.

In my companies, we record every sales call.  We have reviews of the calls at least once per week.

Sometimes, GrowthAssistant sales’ account execs ask me to join their calls, if I have a relationship with the potential client or if they think I can help them close. 

I'll make sure we spend 5 mins after each call to ask them about it.

The answers are definitely important, but the MOST important part of this is to create the culture/mindset of feedback and reflection.

One last pro-tip: especially as a founder, EVERY time I share my story, I tweak it a bit.  And I watch the person. 

I see how they react. Do they respond to my change or ignore it? Is the response positive or negative? Do they seem to relax and nod excitedly?

I never stop practicing it and taking in feedback.

Tweaking and watching the responses helps me with the most important thing: shaping a STRONG narrative.

Let me give you an example of how I tweak my narrative.

When pitching the story of Aux to a potential private equity client, I used to tell the story like this: "My friends in private kept calling me, telling me they didn't understand digital marketing and needed to understand it to evaluate a company they were buying."

As we got into the business, we learned a detail I had never appreciated: the "Investment Committee."

This is the group of people inside a PE firm who the investment partner has to convince to "do the deal." 

It turns out a lot of time at a PE firm is spent on "convincing IC."

After I learned this, I tweaked the narrative: "My friends in PE kept calling and telling me they wanted to buy a business, but their IC asked them questions about digital marketing and they didn't have answers."

All of a sudden, I'd see the person's body language open up.  Some would even smile or laugh. 

My tweak enabled me to speak to them emotionally — to their experiences.  And it showed up quickly in our pipeline.

I learned this tweaking trick from Speech and Debate.

Every 2 months, we had to change topics.  We had to argue both the affirmative and negative convincingly. 

I'd spend weeks on the narrative, writing and practicing it. 

But the real money would come from debating it, tweaking it and adjusting it until I had something close to perfect.

It should also be thoughtfully structured.  Using frameworks to start is totally fine.  I still use a TON.  The key thing is make it your own and keep it authentic. 

• Here is a broad, obvious trend in the world

• That trend is causing this huge issue/problem (for companies like yours)

• (Maybe) agitate that issue

• Enter: MY SOLUTION

• Examples of that solution and why it wins (demo, case studies, etc)

• Next steps - make it clear and easy and put the prospect on "rails"

Put together practice, regular feedback and a strong narrative, and you'll be selling more, faster.

Many founders confide in me that they are afraid of coming across like a "used car salesman" and that hurts their ability to sell.  I hear you — it can be scary to feel judged for pushing your product or service.

So stop pushing.

Try this reframe: Ask yourself, “How am I HELPING this person?”

I'm not saying to bullshit them or yourself.

If your product actually solves a problem, that means soon you will be HELPING someone.  Genuinely put your energy on connecting with that person and trying to help them.  Not only will your passion shine, but you'll bring empathy, as well.  It will feel good and be a killer sales formula.

When you do this right, you’ll crave selling more and enjoy the feeling of helping people.

-jesse