Will

I create educational email courses for cybersecurity companies.
10 years in sales. 4.5 in big cyber to CISOs and CIOs.
GTM junkie. I write what I live.

[Will @willstilllearns]

The question that changes everything: what's actually causing this?

Not what have you tried. Not what's your budget.

What is actually causing this? Then go quiet.

The first answer is almost never the real one.

Ask.

Stop talking.

Find out.

[Will @willstilllearns]

I was drowning in sweat for 45 minutes waiting on the HVAC rep to show up.

He walked in, declared the diagnosis, and quoted the price. No questions.

No listening. Just an answer he'd already decided on.

A thread:

[Will @willstilllearns]

The rep who won my mom's job wasn't fastest or cheapest.

He asked questions before saying anything about the unit.

She mentioned the bedroom never cooled at night.

That one detail changed his entire recommendation.

The first rep never heard it.

[Will @willstilllearns]

Features don't close enterprise deals.

Urgency does.

Build the case that inaction is expensive before you ever talk price.

Do that, and your solution stops being a cost and starts being the obvious answer.

[Will @willstilllearns]

Most enterprise deals don't die to a competitor.

They die to "let's revisit next quarter."

Here's how to make inaction more expensive than your solution:

[Will @willstilllearns]

5 ways to price inaction:

1. Quantify the bleed: downtime, headcount, exposure
2. Walk them 12 months forward
3. Put status quo cost next to your price
4. One quarter on a $2M problem = $500K
5. Find the personal cost: career risk, missed targets

[Will @willstilllearns]

@thesamparr Everything runs in cycles

[GREG ISENBERG @gregisenberg]

The computer is being reinvented in the agentic era:

- The model is the new CPU.
- The harness is the new OS.
- Hallucinations are the new bugs.
- The context window is the new RAM.
- Skills are the new apps.
- Markdown files are the new config.
- Evals are the new QA.
- Context is the new moat.
- Permissions are the new firewall
- Trust is the new bottleneck.
- Prompt is the new programming language
- Agent is the new software.

Anything you dream of, you can build.

This is the greatest time ever to be building with computers.

[Will @willstilllearns]

Where is your biggest gap right now?

Getting information in, getting ideas out, or getting up to speed before the room?

Drop it below. I'll share what's worked for me.

[Will @willstilllearns]

Most people think the AI advantage is about doing more.

It's not.

It's about removing the friction between your best thinking and the world seeing it.

Here's how to find your bottleneck and close the gap 🧵

[Will @willstilllearns]

One warning.

GPS didn't take away your sense of direction in a day. It eroded it across a thousand trips.

The same thing can happen to your thinking.

Every problem you hand to AI instead of sitting with yourself is a rep you didn't take.

Keep the judgment for yourself.

[Will @willstilllearns]

5/ They run their territory like a CEO runs a service business.

Intimate knowledge of their business and competitors.

They know their customers' problems better than the customers can articulate them.

That depth is what earns trust.

[Will @willstilllearns]

Working harder isn't a strategy anymore.

Every rep you're competing against is working hard.

The ones still standing in 5 years won't have outworked the field.

They'll have outbuilt it.

Here's what separates them 🧵

[Will @willstilllearns]

4/ They build a digital brand.

They don't rely on one channel.

In-person events, email, cold calls, gifts, letters, videos.

They show up in the format their buyer actually responds to.