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.

I am thrilled to share that Ian Knight Jr. of Intercom won our Skill Stacker Awards Fiji Trip!

There were 10 contestants who had amazing transformation stories.

Ian's took the cake:
• joined pclub.io while struggling
• exited the year top SMB AE globally
• mastered our discovery frameworks to get there

Congrats Ian. Well deserved.

Let's give him the round of applause he deserves!

$10,000 all-expense paid!

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

Salespeople:

Pro tip if you negotiate with procurement:

Upload your proposal + order form to your favorite AI tool.

Then prompt it:

"Pretend you're a ruthless procurement negotiator. Analyze this seller's proposal in an effort to find any and all negotiation leverage. Tell me where the proposal is vulnerable and how you'd use it against me if you were compensated to secure as much discount as possible."

You might be surprised how often you make innocuous mistakes without realizing it: Things procurement pros see coming a mile away.

The best negotiators anticipate.

If you're blindsided?

You usually lose.

As an FYI:

Today's procurement professionals are doing exactly this:

• Taking your order form, proposal (etc)
• Uploading it to ChatGPT for weaknesses
• Uses those against you

Keep your win/win mindset.

But don't let that stop you from anticipating what might be coming.

P.S. I’m hosting a live masterclass this Thursday for AEs.

I’ll break down 3 modern selling strategies that help you:

• Rewire how buyers think about their problems
• Pour gas on the fire when you find urgency
• Engineer a consensus-building engine

If you’re serious about becoming a top-earning AE, join us.

Register here: https://lnkd.in/eC_ZDJSR

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SaaS Discovery Masterclass

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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

If I could only ask 4 sales questions to uncover deal-closing pain, here they are:

(the order matters)


1. Tell me about your biggest challenges when it comes to X?

Easy enough.

Just kickstart the conversation in the right direction.

And get to the 'heart of the matter' fast.

But not enough by itself. 

Customers will always give surface level answers to the first question.


2. What's going on in the business that's driving [what they shared] to be a priorty?

Ask this, and your customers will chuckle half the time.

Why?

Because you are striking a CHORD when you ask that.

You're getting to the 'need behind the need.'

That's where big money lives.


3. What metric is suffering most as a result of that?

Here's where most sellers struggle:

Quantifying pain.

You walk into a different world when you go from expressed pain to quantified pain.

Your customer's urgency ramps up.

The likelihood of ghosting goes down.

Spending money to solve the problem begins to look obvious.


4. What's driving you to solve all this now rather than later?

Ask this too early?

The answers will be weak.

But if you ask this AFTER those first three questions...

It lands.

Give those a try.

Which stood out most?

P.S. Want a proven list of 50 questions that sell? Here you go: https://lnkd.in/g2giY-ab

Weak sales managers manage calls.

Average sales managers manage deals.

Good sales managers manage forecasts.

Great sales managers manage their people's skills & capabilities.

Because they know one thing:

Revenue is an outcome that expert-skilled sellers produce.

Skill management = proactive management.

Narrowing your ICP will make some buyers feel unwanted... but it will make the right buyers feel "seen." That trade is worth it every time.

Please join me in celebrating these revenue professionals! Yesterday, we ran the 1st annual Skill Stacker Awards.

Members of the pclub.io community submitted their success stories:

• income transformations
• career transformations
• skill transformations

Every story was inspiring. 

But 10 people won the outstanding awards.

Including 1 winner of our Fiji trip giveaway.

Join me in shouting out these revenue professionals.

They are exactly what a commitment to excellence looks like.

Here are the highlights:

Rookie of the Year: Gabrielle Stott
• AE at Warmly
• Previous BDR manager
• Transitioned to 1st year AE
• Overwhelmed and lost, as she started
• Dug in on skill mastery, discovery, negotiation
• Ended up not just at 150% of quota, but #1 seller

Her FIRST year!


Founder-Led Seller of the Year: Frank Bergmann
• Founding AE at StackGuardian
• Started at $0 - closed the first $1M ARR
• Closed five Fortune 500 customers
• Is now their Head of Sales


Biggest Transformation: Scott Rowley
• Started burnt-out and frustrated in another industry
• Transitioned into an AE role at Gainsight
• $1.15M TCV his first year ($690k quota)
• First-ever agentic deal sold for the company



Top 25% Performer Awards

Veronica Rivero Account Director at LinkedIn:
115% in FY25 • $405K TCV Deal • Hit Every Quarter

Lewis Bramley AE at KnowBe4
118% Quota • UK Mid-Market AE of the Year • £33K ACV

Brian Robak, Sr Director at Numerator
$35K → $2M • 150% Quota • Top Mid-Market Rep • Promoted



Top 10% Performer Awards

Stacy Kelly, RM at ICE Mortgage Technologies
#1 on Team • Grew Variable: $85K → $145K 

Imran Mitha AE at Remote
Never Missed Quota • Highest Win Rate Globally • #1 in NA

Chris O'Dowd, AE at Quantum Metric
A whopping $600K+ W2 • Enterprise Consistency

Elijah Gonsalves, MBA, BDR at Salesforce
140% Avg Quota • 5x Consecutive MVP

And finally.

The best all-around success and transformation story:

Ian Knight Jr., AE at Intercom – the winner of our $10k Fiji Trip giveaway.
• Starting the year struggling w/a weak pipeline
• Discovery calls felt like interrogations
• Ended #1 SMB AE globally at Intercom
• Recent promotion to mid market AE

Congrats to all of you. 

Your stories are inspiring.

I hope to see next year even bigger!

Salespeople: if you truly show up every day, the results won’t have a choice.

Some AEs never spent a year getting cursed off of cold calls and it shows.

The most underrated reason for losing deals: Untested assumptions.

90% of AEs can’t build the cost of inaction.

They ask generic questions:

• How does this impact you?
• What’s the cost of doing nothing?

When you ask questions like that?

You're not a trusted advisor.

You're a manipulator.

The best salespeople know something others don't:

Every customer problem creates predictable consequences.

So they design questions around that:

“Justin, you mentioned win rates dropped from 22% to 19%.”

“When I hear that from other scale-ups, it usually drives CAC up.”

“To what extent is that becoming a concern?”

Boom.

Imagine being that buyer.

You don’t feel manipulated.

You feel understood.

Here’s the formula:


STEP 1: Identify the top 2-3 problems you solve.

Most solutions solve a small set of predictable problems.

For me, that’s things like:

• Low win rates
• Weak deal sizes
• Slow sales cycles


STEP 2: Map 2–3 consequences of each problem

Every problem creates repeatable downstream consequences.

Low win rates?

That usually leads to:

• Unsustainable CAC
• Poor morale & attrition

STEP 3: Design your questions.

Simple formula:

“Typically when I hear {{problem}}, it leads to {{consequence}}.

“To what extent is that showing up?”

Basic salespeople don’t ask questions like that.

Trusted consultants do.

Small tweak.

Massive difference.

Last thing:

You didn't used to have to do things like this.

A few years ago, sloppy sales technique was enough.

If you think being an AE is getting harder?

You’re right.

• Quota attainment rates have collapsed
• Buying committees are big and risk averse
• Decisions are made with more scrutiny

It’s 2026 now.

You need to level up.

Because you were trained for a market that no longer exists.

That’s why I’m hosting a live masterclass this Thursday for AEs.

I’ll break down 3 modern selling strategies that help you:

• Rewire how buyers think about their problems
• Pour gas on the fire when you find urgency
• Engineer a consensus-building engine

If you’re serious about becoming a top-earning AE, join us.

Register here: https://lnkd.in/eC_ZDJSR

According to that data, 84% of sales upskilling initiatives fail.

Career to date, I've worked with about 5,000 revenue teams.

I've seen first-hand more attempts at transformation than I count.

Here's what I've learned about what transformation truly takes.

Fail to understand this?

You'll be part of the 84% statistic. 

Let me know what stood out most in the comments.

Career-to-date, I’ve worked with over 5,000 revenue teams. I’ve seen what separates elite revenue teams from the rest. I’ve also seen why 84% of reven

Open article: Why 84% of Revenue Upskilling Fails (And What Elite Teams Do Instead)
 by Chris Orlob • 13 min read

Why 84% of Revenue Upskilling Fails (And What Elite Teams Do Instead)

I’ve written 1,394 LinkedIn posts about Discovery.

But according to the data… I still have more to learn:

Last week, we released AI Skill Intelligence on a limited basis.

It measures your proficiency against industry-standard revenue skills.

So I ran my own discovery calls through it.

Here’s the result:

I have a 78 Overall Rating score on the 'Value Discovery' skill:

"Proficient." Not "Expert."

I thought I knew exactly where my gap would be.

"Go deeper on root cause analysis."

Nope.

I was wrong.

The biggest gap, according to my own data?

I consistently skip building Negative Impact:

The moment where the buyer feels a visceral cost of inaction.

The AI forecasts that if I fix this:

• I reach Expert status in ~2 months
• Win rates improve ~200 basis points

That’s the interesting part.

Now I'm not training for its own sake:

I can see the revenue on the table if I improve.

Skill growth is the most durable growth lever in revenue.

Yet most teams invest almost none of their budget there.

That's about to change.

Because now we can measure and see skills.

Even complex ones that don't fit on a simple call rubric.

When you measure something?

It almost always improves.

P.S. What's the biggest skill gap you think most AEs have today?

A) Shallow discovery
B) Point and click feature demos
C) Struggling to multi-thread
D) Closing motions that lead to slipped deals

Comment below.

The single most underrated enterprise selling skill:

Navigating decision dysfunction.

Always assume that dysfunction is the status quo.

And that it's your job to make it as functional as possible.

That's why you get paid the big bucks in enterprise.

Lone wolf salespeople make commissions.  But they don't make careers.

Excited to be giving away a $10,000 trip for two to Fiji today.

Today is our first ever Annual Skill Stacker Awards.

We'll be awarding our community's top 10 personal sales transformation stories.

And one winner gets to go to Fiji.

Whether you're a member or not, would love to have you join! 

Happening at 9am (pacific): https://lnkd.in/g3ZPbmXN

Salespeople: In the age of AI - If you are not stone-cold excellent at what you do? You will be viewed as an expense.

There is no average anymore.

Average is for losers.

Sales training without skill measurement is "enablement theater."

It's where weak enablement leaders go to hide.

5 years from now?

People will laugh it was ever done this way.

Training with no skill measurement is the new smoking.

The ultimate revenue constraint is the quality of your revenue workforce.

Enterprise sellers: Which of these characteristics separates "enterprise selling" from mid market selling more than any of the others?

A) Deal Size. If you're closing large deals (exact threshold tbd), you're "enterprise."

B) Company size. If you sell to large companies (employee count), you're "enterprise."

C) Complexity. If you deal with complex buying committees, procurement labyrinths, and decision dysfunction, you're "enterprise."

D) C-Suite Altitude. If you sell transformational solutions that demand involvement from the C-Suite, you're "enterprise."

All of these make up enterprise selling in one way or another.

But which stands out as the #1 characteristic?

Salespeople: There's a right way and wrong way to use the product roadmap:

Right way
• Show the direction of your company
• Position yourself as a long term partner
• Cast a vision for where you can go together

Wrong way
• Make promises you cannot keep
• Sell features that do not yet exist
• Give timelines you know nothing of

Use your company's product roadmap as a tool to position yourself as a long-term partner. Not as a tool to trick them into transacting with you.

Sriharsha Guduguntla

CEO at Hyperbound (YC S23) | Helping marketing leaders build pipeline with AI at scale

Call me Sai! I'm the Co-Founder & CEO of Hyperbound. I'm a YCombinator Founder (S23) who's interested in startups and the intersection of AI and sales and marketing. Currently building next-generation GTM tools at https://hyperbound.ai. 🚀 

I'm a self-learned full-stack engineer and designer with experience building software for 12+ years.

http://sriharshaguduguntla.com

Member

$20,000 referral bonus for an engineer that we hire? YES, we are hiring for 6 full-stack software engineers at Hyperbound ASAP to join us in our San Francisco HQ!

We are growing fast and supporting Fortune 100 customers means having a cracked customer-facing engineering team that wants to solve some of the most interesting problems. 

We are making decisions within 30 days. 

Atul Raghunathan and I paid out 2 people in the last month for the same referral bonus.

Send your best.

===================
Please tag your best engineering friends in the comments AND have them apply here at: https://lnkd.in/gyiai-pq

CEO at Hyperbound (YC S23) | Building AI Sales Roleplay Simulations to upskill GTM teams

Hyperbound is in Austin today and ☠️ Belal Batrawy, our Head of Key Accounts, will be speaking about the future of enablement, revenue activation, and the top 6 things that most sales enablement leaders are not doing today that they should!

Location: Austin Hilton, TX
Time: 11:15 AM CT

He will be joined by Nitin Bhoopal and Isaac Hong!

We have a fun after-event at Bull & Bowl, and have just 1 spot left if you're interested in reserving a spot for dinner! DM me!

We're glad we partnered with Anaconda, Inc.!! Its' been an exceptional experience, not to mention, they're customers of Hyperbound as well! 

We couldn't build Hyperbound without them!

Hyperbound needed their AI sales coach to behave like real prospects: skeptical, opinionated, and consistent across thousands of tests. 

Manual evaluations and mismatched environments slowed them down and made compliance harder. By standardizing on conda inside Docker, they cut evaluation cycles from days to hours and completed a SOC 2 Type II audit, showing speed and security don’t have to be a trade-off.

According to CTO and co-founder Atul Raghunathan: "Anaconda became the quiet backbone of our realism testing...Every engineer gets the exact same environment, so we know our test results are consistent and our improvements are real, not just artifacts of different setups."

Explore how Hyperbound proved organizations don’t have to choose between speed and security with our latest case study: https://bit.ly/4pJbO8L

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