Chris Orlob

Grew Gong from $200k to $200M+ | Online Courses for SaaS Sellers (pclub.io) | Solving Revenue Hiring (QuotaSignal)

"You can have anything you want if you master every aspect of selling." My mentor told me that over a burger when I was 22 years old. Having only $40 to my name, along with a wife and my first child to support, I took that seriously. I made a commitment to master every aspect of selling, and to earn more money than I could imagine. And I was going to do it in SaaS.

When I first became an account executive, I struggled to find repeatable, consistent success. Some months I did well. Some I missed by a mile. After reading hundreds of books (literally) and debriefing every one of my sales calls (thousands) in a journal, I started to crack the code, little by little. 

Soon, things started to go incredibly well. I started to earn multiple six figures a year, which helped me launch my first business. Not too long later (after plenty of mistakes!), I joined forces with a little company called Gong.io, while they were doing less than $200,000 a year in ARR. Figured I'd help them grow to $10M and be done.

5.5 years later, we grew from $200k to $200 million in ARR and a $7.2 billion valuation. I was fortunate enough to earn my first seven-figure income. A decade pursuit of mastering every aspect of sales had come to fruition (though I'm still not done). That felt amazing. 

I kept finding myself telling people, "You can have anything you want if you master every aspect of selling," just like my mentor had told me all those years ago. Because I experienced it first-hand.

My passion for mastering every aspect of selling started to extend to helping OTHER people do it. Soon, I started pclub.io - a business dedicated to helping B2B tech salespeople master every aspect of selling (and earn more money than they've ever dreamed of). 

Since starting, I've helped over 11,000 sales professionals and leaders. Many of which have gone on to turbo charge their sales success:

“Exceeded 245% of my target." -Christian Allen, AE at ZoomInfo

"CLOSED the most ARR in company history” -Marshall Weil, AE at Freewill

"Made 152% of my number” -Jasi Johnson, AE at Gartner

"I made it to Club One - the new program rolled out for the top 1%. -David Rosenstein, AE at LinkedIn


Many of these stories included people who started out thinking, "Maybe this is possible for other talented people, but not for me." But selling is nothing more than a series of skills. Anyone can master it, and I can teach you how.

Like I always tell people, "you can have anything you want if you master every aspect of selling."

Begin writing YOUR success story by visiting www.pclub.io

Co-Founder & CEO

pclub.io is the #1 skill transformation platform for revenue teams. We work with the top 0.01% of sales earners, practitioners, and leaders to create top-rated online courses that help you grow your sales skills to life-altering levels. Instead of spending years mastering sales through trial and error or going through stodgy ‘one size fits all’ sales training, you’ll get to the steal the playbooks, frameworks, and skills of the top 0.01% sales earners on the planet, accelerating your mastery curve, income, and revenue to unrecognizable levels.

Revenue leaders: After working with 5,000 revenue orgs, I've noticed a pattern in high performing sales teams:

Very few of them them use a "sales methodology."

The do something far more effective.

The term “sales methodology” emerged in the 1970s and 80s.

And back then, it did something transformational:

It brought structure to a profession that operated like the wild west, fueled by personality, charisma, and long, boozy lunches.

But that was 40–50 years ago.

In today’s advanced sales environment, the term doesn’t just fall short – it actually creates more harm than good.

Here's why.

Let me know what you think in the comments.

CEO at pclub.io - helped grow Gong from $200K ARR to $200M+ ARR | Advancing the revenue profession forward.

The term “sales methodology” emerged in the 1970s and 80s. And back then, it did something transformational: It brought structure to a profession that

Open article: Sales Methodologies Are Dead. Here’s What Top Revenue Leaders Are Doing Instead.  by Chris Orlob • 7 min read

Sales Methodologies Are Dead. Here’s What Top Revenue Leaders Are Doing Instead.

99% of AEs ask the wrong questions during demos.

They ask: "What questions do you have?"

Or: "Does that make sense?"

Those don't sell. 

They just fill the silence.

Here are 10 questions that actually move deals forward:

1) Before you demo a feature:

"How are you doing [X workflow] today?"

→ Creates contrast between their current state and your solution.

2) After you demo a feature:

"How does that compare to how you're doing it now?"

→ Reinforces the contrast. Locks in value.

3) Mid-demo pulse check:

"To what degree is this resonating so far?"

→ Way better than "any questions?"

4) Get them visualizing:

"To what extent do you envision this being useful in your situation?"

→ Gets them imagining themselves using your product.

5) For decision makers who don't use the product:

"How do you see your team using that?"

→ Helps them see the value even if they're not hands-on.

6) Close the loop on pain:

"To what extent do you see that solving [problem they shared earlier]?"

→ Connects pain to solution explicitly.

7) Get them to voice benefits:

"What benefits do you see showing up in your world from this?"

→ When they say it, they believe it more.

8) When you strike a chord:

"It seems like that resonated, what challenge in your business makes that hit home?"

→ Uncovers gold when you've hit a nerve.

9) When you're off track:

"It seems like this isn't resonating, where am I missing the mark?"

→ Gets you back on track fast.

10) Pattern interrupt version of "any questions":

"Where do you want to double-click with a few questions?"

→ Same intent, but sounds different than every other rep.

The difference?

The first two questions put the spotlight on you.

These 10 put the spotlight on them.

That's where selling happens.

P.S. If you want the exact 50 questions I use to build pain, urgency, and desire in deals, grab the full list here ➡️ https://lnkd.in/g2giY-ab

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CEO at pclub.io - Skill Transformation for Revenue Teams. Trained 11,000+ sales professionals and leaders. MSG ME if you're looking to upskill your SaaS sales or revenue team.

Upskill Your Revenue Team and Boost Win Rates

"How to Master Every Aspect of SaaS Sales, Close More Deals, And Sell In An Economic Meltdown"

30 Deal-Closing SaaS Sales Scripts

We are hiring an Account Director here at pclub.io to manage, expand, and renew key customer accounts ($30k-$200k ACVs).

$200,000 OTE with retroactive comp plan accelerators that have a clear path to $250,000 to $300,000 in annual earnings.

Responsible for:
- 25-30 key accounts
- relationship orchestration & multi-threading
- renewals and strategic expansions (3 upsell levers)
- partner closely with our ProServ team

We have one spot and a growing pipeline of candidates, so this is probably "last call" for this round of hiring.

DM if interested.

Two worst questions salespeople ask on sales demos:

"Does that make sense?"

"Do you have any questions?"

Here's three (much better) questions:

1. "How does that compare to how you solve this today?"

This is magic.

Because instead of criticizing the feature you just showed...

Now they're thinking about the sh*tty way they handle the problem today.

And you're seen in a better light.

2. "To what extent is this resonating so far?"

Life hack:

You can turn any close-end question into an open-ended question by starting it with this phrase:

"To what extent..."

3. "To what extent does that solve [x pain point they shared earlier]?"

This puts closure on a problem.

Explicitly connects the dots that your solution will solve their problem.

...assuming you did a good job.

P.S. If you want the exact 50 questions I use to build pain, urgency, and desire in deals, grab the full list here ➡️ https://lnkd.in/g2giY-ab

Your demos aren't closing deals.

Here's why:

You're showing features without framing value.

Most AEs think: "If I show them enough cool stuff, they'll buy."

Wrong.

Buyers don't buy features. 

They buy outcomes.

Here's the demo framework that's closed over $100M in SaaS deals:

The FAVORITE Framework

(Use this for EACH capability you demo)

F - Frame the pain (10 seconds)

Before you show anything:

"A lot of sales leaders tell me they're struggling with getting new reps up to speed. Complex demos take forever to learn."

You're setting context. Creating contrast.

A - Ask a question (10 seconds)

"How are you dealing with that today?"

Now they're talking. It's a conversation, not a presentation.

V - Visualize the outcome (10 seconds)

"Imagine being able to cut your ramp time in half by getting your reps to master their demo in weeks instead of months."

Mental pictures drive behavior.

O - Orient them to the screen (30 seconds)

"Let me orient you to what you're looking at..."

Most buyers are thinking: "What the hell am I looking at?"

Don't skip this. The confused mind says no.

R - Reveal the workflow (2 minutes)

Now you actually demo the feature.

But notice: you've surrounded it with value.

I - Implant the value (10 seconds)

After the demo:

"To sum that up, this will help you stop losing deals because your reps can't demo effectively."

Don't leave value to chance.

T - Tell a story (15 seconds)

"One of our customers used this to cut ramp time from 7 months to 4 months."

Stories stick. Features don't.

E - Elicit a response (Question)

"How does that compare to how you're solving this today?"

Get them talking again.

The pattern you should see:

Value → Value → Value → Feature → Value → Story → Question

You're not just showing features.

You're wrapping every feature in a blanket of value.

Most reps do this:

Feature → Feature → Feature → "Any questions?"

Then wonder why deals stall.

Top reps do this:

Pain → Outcome → Feature → Value → Story

Then close deals others can't.

This framework takes practice.

The first time will feel choppy.

But master this, and you'll never struggle with demos again.

What's the biggest mistake you see in demos?

P.S. If you want the exact 50 questions I use to build pain, urgency, and desire in deals, grab the full list here ➡️ https://lnkd.in/g2giY-ab

Revenue leaders: After working with 5,000 revenue orgs, I've seen 5 habits in every great revenue team.

From InsideSales, to scaling Gong, to now leading pclub, my entire career has been built around a single mission:

To understand what separates top-performing revenue teams from the rest.

Across those thousands of companies, five habits show up again and again.

These are governing laws of revenue performance. 

Not random acts of tactics.

And only elite revenue teams have all five operationalized.

We are hiring a mid market / lower enterprise Account Manager role here at pclub.io!

This is not a CSM role. 

It's a commercial role:

• Renewal revenue
• Expansion revenue
• Power relationships
• Data-driven executive reviews
• $50k-$100k typical accounts

Must be excellent at:
• discovery 
• business acumen
• value narrative control
• complex multi-threading
• understand how revenue orgs operate

You'll partner closely with our ProServ team, who:
• Manage customer deployments
• Drive value realization

DM me if you're interested.

The promise?
• Competitive OTE
• World-class professional dev.
• Equity in a category-creating startup
• The ability to design & build, not just execute

DM if you're interested (or know someone who is).

pclub.io

Unpopular opinion: Getting a case study in exchange for a discount is the absolute 101 bare minimum of negotiation skill. 

Yet it's talked about like it's an advanced tactic.

Yes, it's better than giving a discount with nothing in return.

But getting a promise for a case study in exchange for 30% off is not a win.

It's table stakes.

If someone teaches you this as if it's the HEIGHT of negotiation skill?

Red flag.

93% of AEs can't sell to the C-Suite and it shows: Only 7% of C-Suite execs rates sales calls as valuable enough to agree to a follow up (Gartner).

Good news?

It's an easy fix.

4 tips to sell to the C-Suite like the top 7%:

1. Don't make the C-Suite your first meeting.

You’ll be tempted to go after the CXO first.

Don’t.

Unless you already have inside info:

Do your homework first.

The worst thing you can do?

Show up to the C-Suite empty-handed.

Do a few “rounds” first.

Pay your dues.

2. Start the meeting with a “What I Know” slide.

Most CXOs expect sales calls to be a waste.

They rarely agree to them.

When they do, they do it reluctantly.

But.

The top 10% of sellers earn instant credibility by starting the meeting like this:

“Ok.

"I’ve talked to 3 people in your org, read your 10K, and researched your industry.

"Let's start with a summary of what I’ve learned.”

INSTANT CREDIBILITY.

“Wow, the first time a sales call isn’t a waste,” they’ll think.

The rest is yours to lose.

3. RESEARCH-BASED Discovery Only

This is not the time for typical discovery.

You should have done that by now.

That doesn’t mean you can’t ask questions.

But.

They better be informed.

They better be targeted.

They better share observations.

BAD EXAMPLE:

“Tell me about your function's biggest challenges.”

GOOD EXAMPLE:

“When I talked to John, he said the company was struggling to recruit engineers to get new features to market fast enough.

"His concern was hitting deadlines, but I have to imagine you have a broader view of why this issue matters.

"Assuming this is a top-of-mind issue, how about we start by getting your take on that?”

Do that.

That's how you get them listening.

4. Lean on your champion for TACTICAL next steps.

Don't try to “lock in next steps” with the CXO.

They start their day at 7am and end at 7pm.

Yes, you want to talk again.

But use your champion for 'tactical' next steps.

Reserve C-Suite next steps for strategic meetings.

Say this:

“I think Lisa and I can take next steps from here.

"I’ll keep you in the loop. The one meeting I do think we should have next will be in three weeks from now where we debrief the business case.

"Between now and then you’re off the hook, but mind if I go through your EA so that you, me, and Lisa can review this a few weeks out?”

“This person gets it,” they’ll think.

Master these 4 moves and you'll join the top 7% who actually get C-Suite follow-ups.

But here's the thing:

Selling to the C-Suite is just one part of the equation.

You also need the right questions throughout the entire deal cycle.

P.S. If you want the exact 50 questions I use to build pain, urgency, and desire in deals, grab the full list here ➡️ https://lnkd.in/g2giY-ab

Most AEs stop discovery too early.

As soon as they hear a problem:

They jump in with: "We can help with that!"

So they only uncover "little pains."

And little pains get you little deals.

Big deals come from building negative impact.

Here's the 3-step framework I use to create urgency in every discovery call:

Step 1: Summarize the business problem.

After your initial discovery, pause and recap:

"Let me see if I got this right..."

Then summarize what you've heard.

Get confirmation before moving forward.

This shows you're listening and sets up the next step perfectly.

Step 2: Ask an open-ended impact question.

This is where most reps fail.

They skip straight to pitching.

Instead, ask:

"Can you help me understand the ripple effects this challenge is having on the rest of the business?"

Notice the phrase "ripple effects", it's far more effective than "impact."

It sounds less salesy and triggers deeper thinking.

Step 3: Ask targeted impact questions.

Now that they're talking, funnel them toward specific consequences:

- "How is this affecting your cost of acquisition?"
- "To what extent is marketing impacted by this?"
- "Is your CFO concerned with this metric?"

The order matters.

Open question first, they feel in control.

Targeted questions second = you guide the conversation.

Why this works:

With greater negative impact comes three things:

→ Higher urgency

→ Bigger deal sizes

→ Access to power

Most reps think discovery is about finding problems.

Wrong.

Discovery is about exploring the *consequences* of those problems.

That's what drives emotion.

And emotion drives purchase decisions.

💡 Rule of thumb: You've hit paydirt when the problem would be discussed in an executive meeting.

No exec talks about "needing better visibility."

But they do talk about cash flow, valuation, and market share.

P.S. If you want the exact 50 questions I use to build pain, urgency, and desire in deals, grab the full list here ➡️ https://lnkd.in/g2giY-ab

Most AEs do not have enough "GTFO of my pipeline" energy.

The best salespeople can quote you a $600,000 price without flinching. 

They talk about price like they're talking about the salad they're having for lunch:

Totally casual.

Zero hangups.

Pass the salt, por favor.

Less successful salespeople?

They tremble, shake, and overcompensate when price comes up.

They're not comfortable talking about big dollars and it shows.

It's as if they're apologizing for their price.

They'll go on 3 minute rants justifying why their price is the way it is, without being asked.

The turning point comes from when you realize the value you provide is a tsunami compared to the tiny $600,000 check you're asking for.

Find a way to get comfortable with money.

Otherwise you'll find yourself "throwing the game."

P.S. If you want the exact 50 questions I use to build pain, urgency, and desire in deals, grab the full list here ➡️ https://lnkd.in/g2giY-ab

21 sales lessons I wish I knew at $200k ARR that I learned at $200M ARR:

1. Money follows pain.
Stop selling benefits.
Start selling pain relief.
You'll close more.

2. WHO matters more than WHAT.
If you're talking to the right person:
But you have bad sales technique?
You can still win.
If you're talking to the wrong person:
And have great sales technique?
You lose.

3. Don't multi-thread.
Single-thread with multiple people.
Break people out into 1:1 meetings.
Stole this from Krysten Conner.

4. Don't multi-thread too much.
Looping in the wrong people can kill your deal.
Get the blend of people just right.
No, IT doesn't always need to be involved.

5. Great cold emails don't talk about your product.
They talk about pain.
They look like a page from your buyer's diary.

6. Follow up. Fast.
Some sellers take days to follow up.
They don't want to seem desperate.
Stop it. This isn't dating.
Speed sells.

7. The secret to enterprise deals:
Pick the deals you can win; then win the deals you pick.

8. Build your business acumen.
It makes your sales techniques 2x as effective.
Without acumen, you're hollow.

9. Don't seek approval.
Seek to solve problems.
Big difference.
Don't grovel.

10. Buyers don't buy because of ROI.
ROI doesn't drive purchases.
Emotion does.
They simply need ROI to justify the purchase.

11. There are two winners in each deal:
The seller who won.
The seller who ejected from the deal early and didn't waste time.

12. "Continuity of power" is the ultimate metric.
Getting access to power is one thing.
Getting a 2nd or 3rd meeting with power is entirely different.
Only sellers with sharp acumen get the latter.

13. Great sales calls start with planning.
Don't wing it.

14. Voice tone matters.
Stop inflecting up.
Inflect down.
It sets an equal tone.

15. Become a master wordsmith.
Words trigger mental pictures.
Mental pictures trigger emotions.
Emotions trigger actions.
Actions close deals.

16. Don't negotiate price too early.
It should be the last thing you do before the deal closes.
Anything else is too early.

17. Talk about money like it's nothing.
Quote a $600,000 proposal with a straight face.
That's a super power.
The best salespeople have a casual attitude about money.
The worst salespeople freak out when they talk numbers.

18. Selling is a set of skills.
Not a personality trait.

19. Use the same words your buyer uses.
Stop paraphrasing.
Stop putting your own twist on things.
Use their words.

20. Always know the next step.
Bad news:
If you don't know what next step you'll suggest?
You're wasting that sales call.
Selling is an act of leadership.
So lead.

P.S. If you want the exact 50 questions I use to build pain, urgency, and desire in deals, grab the full list here ➡️ https://lnkd.in/g2giY-ab

Sales leaders: 

There are two main “units of management” in your job:

- Your people’s deals
- Your people’s skills

If you are only managing one of those, you are incomplete as a revenue leader.

Deal management takes care of today.

Skill management takes care of the future.

The worst way to spend your days as a salesperson?

Chasing.

When a buyer has no problem (even after some education)?

Bad sellers try to convince them that they do.

The best salespeople never do this.

The best salespeople attract, not chase.

When a buyer doesn't have a problem, even after a fair shake?

They say things like this:

"Sounds like things are going amazingly well. If that's the case, I'm not sure we can help you. Does that check out with you, or am I missing a piece to the puzzle?"

One of two things happen:

1. Your buyer agrees.

"Yep, that's the vibe I'm getting too."

Congrats.

You just saved a lot of time and heartache.

Next.

2. Your buyer opens up.

"Actually yes, you are missing something..."

Their defenses melt.

Their sales resistance drops.

They share what's going on.

Game on.

Sales is a game of social dynamics.

Desperation kills deals.

The best salespeople sell from a place of strength.

Not neediness.

At least, that's my experience.

Is that yours too?

P.S. If you want the exact 50 questions I use to build pain, urgency, and desire in deals, grab the full list here ➡️ https://lnkd.in/g2giY-ab

90% of AEs ask "random acts of discovery questions."

• a problem question here
• a qualification question there
• an impact question over there

The results are predictable: 

Most AEs miss their number.

The top 10% of AEs don't do random acts of questions.

They follow frameworks that choreograph the buyer's psychology.

Here's an example:

• STEP 1: Uncover a high-priority pain
• STEP 2: Quantify the current stage
• STEP 3: Identify the root causes
• STEP 4: Build negative impact
• STEP 5: Contrast with future state

Then, they ask questions that serve the model.

This isn't a checklist.

This is a mental model for problem-solving.

Don't let the tail wag the dog:

The mental model comes first.

Questions come next: 

They are your execution tool.

But don't get that backwards.

Otherwise, you're doing random acts of questioning.

Congrats Mohamed on 188% to quota.

No "sales gymnastics" required :) 

P.S. When you ask questions within the right framework, they become 2x as powerful as sales weapons. 

Here's 50 powerful sales questions that aren't random, but instead follow a model: https://lnkd.in/g2giY-ab

Inventing the way B2B software companies sell over WhatsApp.

The best revenue leaders manage skills, not just deals.

Deals take care of today. Skills take care of forever.

The best treat skills like a 👏 managed 👏 asset.

Investing in your skills is the single best demonstration of having an internal locus of control.

For the last 15 years, I’ve been inside the engine rooms of more than 5,000 revenue organizations.

From InsideSales.com, to Gong, to pclub.io, my entire career has been built around a single mission:

To understand - with clarity - what actually separates top-performing sales teams from the rest

Across those thousands of companies, five patterns show up again and again.

Here they are.

CEO at pclub.io - helped grow Gong from $200K ARR to $200M+ ARR, now building the platform to uplevel the global revenue workforce.

Revenue pros: I now officially own the domain Caliber.io and I'm strongly considering changing the name of pclub.io to Caliber.

I like Caliber for a few reasons
• Less limiting (pclub = AE-only resonance)
• Speaks to the identity we deliver (become high caliber)
• Less "weird," frankly

What do you think? Change to Caliber? Or stick with pclub?

Packsize LLC

Regional Sales Manager

•	Collaborate with Area Managers to diagnose and evaluate potential Packsize system implementation; resulting in familiarity with diagnostic complex sale strategy and complex sale value proposition. 
•	Manage sales documentation (such as proposals and contracts) and reporting process for two Area Managers; regularly strategize with Director of Finance on creative pricing solutions.
•	Assist Area Managers in management of pipeline and selling process related to territory and account opportunities

Inside Sales Manager

World's leading provider of lean manufacturing services to businesses with complex corrugated packaging needs.

Financial Planning & Analysis

Zions Bank

Structured Finance Group - originated, structured and executed bank loans and other complex financings for corporate clients and financial sponsors. Transactions included leverage buyouts, refinancings, and restructurings.

Sponsor Finance Credit Analyst

National Capital Partners

Analyst, focusing on financial modeling and valuation efforts for investments in the western U.S.

Private Equity Analyst

Energetic sales professional with complex sales experience and a proven track record of overachieving. 

Specialties: Creating true win/win environments by helping Fortune 500 companies to increase efficiency and reduce cost through the implementation of lean on-demand packaging technology. On average our customers realize process improvement and true bottom line savings of 20% to 35%.



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The Battle

Chris Orlob

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