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

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.

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.

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.

Founder @ FDTC → I help startups go from $100K-$15M by improving sales processes, playbooks, & people → Building the #1 SaaS sales coaching program for AEs → Featured in Techstars & Sales Hacker → #helpmedontsellme

It was Monday morning, 11 AM when I went to my boss and said, “I’m sorry, this job, sales...it’s not for me” and I left.

That was 13+ years ago.

At 22 years old I landed my first real job fresh out of college ready to be a “career person.”

I crushed the interview.

But when I came into work for my first day at 10am, I quickly realized that I was scared sh**less of sales, and quit within the first hour.

For the next 3 years, I had PTSD and avoided sales like the plague.

I played it safe and stayed in my comfort zone.

No sales-related stuff whatsoever.

I lost my confidence and ambition. 

I missed career opportunities and wasted away my early 20s.

Fast forward to present day:

I'm a former 2X VP of Sales who took 1 startup from $0 ARR to ≈ $10M ARR in 4 years, and another from $1.5M to ≈ $4.6M ARR in 18 months.

I now teaching SMB AEs and teams how to be top sellers, make higher 6-figures, and get promoted through repeatable systems and playbooks.


Want to learn more? Book a clarity call: https://calendly.com/fdtc/30min 


P.S.⚠️ Grab my top (FREE) 24 discovery questions 6,000+ salespeople are using: https://bit.ly/4d3B2sl


Otherwise, you can find me here:
► YouTube: https://www.youtube.com/@demotoclose
► iTunes: https://apple.co/3Fome9g | Spotify: https://spoti.fi/408V0LS
► Twitter: https://twitter.com/@mistamor

Mor Assouline

I used to say I have no time to work out.

A 30–45 min workout isn’t just 30–45 min.

Between commuting + showering it’s at least 1–2 hours.

But what if it didn’t have to be?

3 of the best purchases I made over the last 6 months:
	1.	A pull up/dip bar for my office
	2.	A stand up desk
	3.	An in office treadmill

All are in office.

Requires 0 commute.

Integrated in my work.

I made it too easy for myself to say yes.

Founder @ Demo to Close | “Success feels like luck. I don’t have a repeatable process.” → I coach SMB & MM AEs on the system for predictable performance | 2X VP of Sales

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SMB sales is overwhelming.

Unlike ENT, it feels like you don’t have time to breathe.

I’ve been there.

- Running 5-6 sales calls every day.
- No time to prep for next meeting.
- Forgetting to follow your call structure.

It’s a lot.

So here’s how I'd reset my focus before the next call:

I’d have a pre call ritual.

Before every call, I’d take a walk around the office, and mentally rehearse what’s about to happen.

It worked for me.

What’s yours?

I audited 47 discovery calls. Inbound close rate = 45%. Outbound close rate =17%. Same MM AE, same approach, but completely different results.

They forgot the most important part of discovery:

You should not treat inbound and outbound leads the same way.

Inbound prospects:
- Raised their hand
- Have a problem they're trying to solve
- Expect to be challenged and questioned

You can be direct: "What's broken that made you reach out?"

Outbound prospects:
- Didn't ask to talk to you
- You're coming to them
- Need context before they'll engage
- You have to earn the right to ask questions

The principle: Your approach should match their entry point.

Inbound = Permission granted They gave you permission by raising their hand. Use it.

Outbound = Permission required You need to earn the right to dig deeper.

Example:
Wrong way with outbound: 
→ "What challenges are you facing with your current system?" (They're thinking: "Who is this person and why should I tell them anything?")

Right way with outbound: 
→ "When I speak with [personas], they tell me they're dealing with [problem A], [problem B] or [Problem C]. So when I did some research, I noticed [relevant trigger] and was wondering if any of that is also something you're experiencing too?"

The lesson: Stop using the same playbook for different situations.

Read the room and map your approach to where the buyer lives.


P.S. Here are 24 of the top discovery questions 7,000+ AEs have been using: https://lnkd.in/eR69raD4

A mid-market AE I just started coaching told me his problem is "inconsistent prospecting." I asked him to screen share and show me his process. 

I found the real problem within 5 minutes.

Me: What does inconsistent mean?

Him: prospects once or twice a month instead of weekly.

Me: Why?

Him: It takes 3-4 hours and it's exhausting.

Me: Okay. But why does it take 3-4 hours? What are you actually doing 
during those 3-4 hours?

Him: He logs into database directory, searches a specific vertical and adds 
some criteria, opens 50+ websites. Decides if each one is a fit.

Me: How does you decide which is worth going after?

Him: Gut feel. I just know when I see it.

Me: What IS gut feel?

Him: don't know. It's like... I can't explain it. I just know based on certain 
things I’m noticing.

Me: sounds like its a mix of certain criteria and intuition?

Him: Yes

Me: "So your brain has seen hundreds of companies. Some closed. Some 
didn't. Your brain learned patterns. What "good" looks like. But you never made those patterns conscious. So you can't fully articulate them."

Him: Yeah, exactly. That's the problem. It only works when I do it.

That's the actual bottleneck.

His knowledge is trapped in his subconscious and he’s working off of intuition.

So here's what we're doing:

Step 1: Figure out what his brain is actually looking for.

Pull every deal he closed won → Feed it into Claude → See what's consistent.

The goal: find the patterns of what good looks like.


Step 2: Write it down.

Once we know what "good" looks like, we make it a checklist.

Now it's not in his head (step 1 and 2 will be tedious at first).


Step 3: Let Claude do the work.

Export companies from the data base results that match the initial criteria and upload to Claudecowork.

Claude checks each website against the checklist and returns the good ones.

20 minutes instead of 3-4 hours.

He’ll be able to build more pipeline, faster.

His "intuition" won't be stuck in his head anymore.

It's in a system.

Which means he can repeat it and scale it



P.S. I’ve been spending 3-4 hours a day vibe coding. All this AI can be overwhelming if you don't know where to point it to. The easiest place to start, at least for me, is looking at what tasks are draining my time that I'm doing manually that I can automate.

Every week I run a group coaching call for AEs at companies like LinkedIn, Hubspot, Klaviyo, Nooks, etc.

Every week after the call, I'd spend 30+ minutes doing the same thing:
→ Pull up the Fathom recording
→ Read through the transcript
→ Summarize the key topics
→ Format everything into a lesson
→ Publish it to our learning portal
→ Copy the topics into Slack for the community

It's not hard work.

But it's tedious as hell and eats at my calendar.

So I automated the entire thing with AI (via Claude Cowork).

Now, every Friday at 1:00 PM, a Claude task kicks off automatically.

It opens Fathom, extracts the full transcript, identifies the coaching topics, generates a formatted title and "How to..." summary for each topic, creates and publishes the lesson in Kajabi, moves it to the top of the course, and posts a recap to our Slack channel.

The whole workflow runs itself. I just show up, coach, and it's done.

Fathom uses encrypted video streaming that blocks automated downloads. Kajabi's drag-and-drop needed custom browser scripting to reorder lessons. The "simple" automation required real problem-solving at every point.

Some lessons I'm learning:
1. "Automate everything" is the wrong goal.
2. Recurring tasks are the highest ROI automation targets.
3. AI agents are better at browser automation than you'd expect.
4. The bottleneck is rarely the AI.

We're entering a whole new era where the competitive advantage isn't knowing how to use AI, but it's knowing how to wire AI into your actual workflows.

If you're a seller or sales leader doing repetitive pre or post-session work every week you're sitting on hours of reclaimed time (houuuurs)




P.S. I’ve been coaching AEs in my community on how to leverage AI in sales. Feb and March coaching slots are sold out, but if you’re interested in joining HMU, we have a waitlist.

See this woman to the left?

If you're in SaaS sales, you might not recognize her.

Her name is Erica Feidner

She's known as the Piano Matchmaker

And every serious salesperson should study her.

Inc. called her one of the top 10 salespeople of all time.

She was Steinway & Sons's top salesperson for a decade & sold over $40M in pianos.

Here are 5 things she does that puts her in another league:

1. REDEFINE YOUR ROLE:
Erica refers to herself as a "piano matchmaker" rather than a salesperson.

Her: "My passion in life is to pair people to pianos in a way that reflects their lifestyle and their personality."

That means YOUR solution may not be the right fit for your prospect (and that's okay)

It took me years to realize not every interested prospect is a fit.

Instead of being a salesperson, be a [solution] matchmaker.


2. PRIORITIZE CLIENT EXPERIENCE OVER THE SALE:
The best salespeople know that buyers don't want to be sold, they want to be helped.

They know that if a prospect feels good with you early on, you're closer to making a deal.

Erica: "What I try to bring to the floor is a wonderful experience for clients and finding exactly the right piano that is in line with their needs and financial comfort zone."

If your prospect's highest priority is price, consider showing them a range of your rates first.

Every sales call should be customized.


3. DON'T RUSH TO MAKE THE SALE:
If the perfect piano isn't available, Erica tells clients to wait until she finds the right one, even at the risk of them purchasing elsewhere.

Her: "If I feel that the piano isn't perfect, I'll tell them to go home and I'll call them when I find the right one."

But, this is exactly how she builds trust and credibility.

I closed a Series D company last year to do onsite sales training for their AEs.

I told the head of sales I'd rather we slow down just to make sure I'm the right fit.

We spent an extra 2 days doing more due diligence.

I earned his trust and closed the deal.


4. READ THE ROOM:
Use conversational cues and body language to understand what the client's sentiment is.

Erica: "I listen to the tone of their voice, the speed of their voice, eye contact or not."

This is why turning on webcam first on Zooms is table stakes.

Example: If your prospect raises their eyebrows in surprise during your sales demo, that's an indicator that they're impressed.

"Sam, seems like this is striking a chord with you?"


5. ADAPT BY PERSONA:
Customize your communication style to fit the client's background and preferences.

Erica: "For instance, engineers might need detailed technical information, while musicians might prioritize sound quality. Once I figured that out, I can speak in a language that they understand best."

For example: In my experience, meet with your prospect before a demo to understand who's showing up and what they care about.

I used to make the mistake of winging it and showing up half prepared.

Half prepared = not prepared.

I review 30+ calls a week for the reps I coach. This is the single most expensive habit I see (it's not discovery).

I was reviewing a call last week where the rep did everything right.

Really solid discovery and demo. 

Then he showed pricing.

Prospect said: "Hmm, that's a bit more than we expected."

And the rep, without missing a beat, said: "Yeah, so we actually have some Q4 pricing incentives right now. If you move forward by end of month, I can probably get you a better rate."

Nobody asked for a discount.

The prospect hadn't said they couldn't afford it.

Hadn't even finished their thought.

The rep just gave it away.

Here's what happens when you do that:

1. You tell the buyer the price was never real. 
2. And you train them to expect a deal every single time you show a number. 

So now every future conversation with that buyer starts with them waiting for you to cave.

I call this flinching.

Most reps don't even realize they're doing it. 

They hear "that's more than expected" and their brain skips to "I'm about to lose this deal."

So they reach for the only tool they think will save it.

The problem: "that's more than we expected" means completely different things depending on who's saying it and why. 

Each version needs a different response.

If you flinch before figuring out which one you're dealing with, you give away money for nothing.

Stop treating every pricing pushback the same. 

Start diagnosing before you respond.

I'm breaking down the full framework in Monday's newsletter. The diagnosis, the talk tracks, all of it (including a cheatsheet you can use).

Read it here tomorrow along with 6.6K+ sellers: demotoclose.com/newsletter


P.S.  It's my birthday today. Instead of cake, I'm giving you a newsletter that'll save you thousands in commission.

I'm consulting for a company that raised over $120M, and we've built AI agents based on my sales methodology to audit thousands of sales calls at scale and score them automatically.

The results are automatically fed into:

a) Slack - real time notifications
b) Salesforce - to generate report on trends

We’re using this to coach reps on high leverage strategies.

It took us about 1.5 months to get to v1 (and still tweaking it)

But the takeaway from implementing this is:
1. What is a high frequency task
2. That is low complexity
3. But is manual and guzzles time,
4. That you can chop up into smaller mini tasks?

Build an AI agent around that and tinker.

Then do it again, and tinker.

You won’t learn about how to be an AI native by reading about it all day.

This is where I built my confidence in sales.

Wearing a suit and door knocking during in Miami (in summer...it's hot).

The cheapest homes in this neighborhood are $10M-$15M.

2 years prior I had quit my first sales job because I was scared.

That notebook you see me holding was a list of all the homeowners that told us to F off.

I had to make sure we never knocked on their homes again.

I never closed a single deal that year in that neighborhood.

But I walked away with a sales MBA

The one thing that can compensate for lack of sales skill is confidence.

And after 1 year of door knocking and cold calling I was confident as hell.

That’s how I eventually found myself in tech sales and teaching others how to be confident and sell better.

First as an early stage AE.

Then as a 2X VP of sales.

Here are 14 (of the many) rules that will never be dead in sales that I've learned:

1. Always show up even if you're not in the mood

2. Don't move onto another skill until you've improved the current one

3. You'll sell more when asking questions vs talking/pitching

4. Always have a compelling reason for the prospect to listen/show up

5. A few bad experiences and screw ups doesn't mean YOU are a screw up

6. You'll always learn more when you fail vs succeed

7. Betting on yourself is the best seed you can plant

8. Surround yourself with people who you look up to

9. Affirmations are cheesy until you do it consistently

10. Community is underrated, never do it alone.

11. Expect the work to be harder/longer than what you anticipated 

12. There is always a trade-off, always.

13. How you say things is sometimes more important than what you say.

14. Building a brand makes sales so much easier

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The Battle

Chris Orlob

Mor Assouline

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Chris Orlob's LinkedIn Performance

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