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

CEO at pclub.io - helped grow Gong from $200K ARR to $200M+ ARR, now building the platform to uplevel the global revenue workforce. 50-year time horizon.

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

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.

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

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.

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

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).

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

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

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.

This article is not for those looking for shiny tools, random tactics, or quick wins that do not compound. It's for those looking to grow revenue thro

Open article: 5 Habits of Elite Revenue Teams (Based on 5,000 Companies) by Chris Orlob • 21 min read

5 Habits of Elite Revenue Teams (Based on 5,000 Companies)

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

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

PSA: You cannot lead people via Slack messages.

There’s a sharp divide forming among revenue leaders in 2026. For a lot of them… it’s not looking good.

I’m seeing to classes of revenue leaders emerge:

• Extractors
• Investors

Extractors live for deals.

Deals. Pipeline. This quarter. This number.

That’s their love language.

People are secondary.

They talk a big game when it comes to:
• Skill development
• Enablement
• training

But their actions make one thing clear:

It’s the furthest thing from their mind.

Don’t get it wrong:

Nothing wrong with focusing on deals.

After all, closing revenue is the job.

But then you meet the second class:

"Investors."

This class of revenue leaders separates the important from the urgent.

Yes, they care about deals.

But they understand something most don’t:

Sellers with fragile skills lose deals.

Sellers with with durable skills close deals.

So just as they manage their team's *pipeline*?

They also manage their team's *skills*.

• They measure them.
• They train them.
• They practice them.
• They reinforce them.
• And they repeat it all until they 👏 can 👏 not 👏 fail.

Because here’s the truth:

Revenue is a skill-constrained system.

Because now that we're out of the "go go" days of tech spend?

Skill is the new growth lever.

Closing deals is how you take care of today.

Building skills is how you take care of the year.

P.S. Want to measure, upgrade, and quantify your revenue team’s skills? Talk to my team here: https://www.pclub.io/

By 2029, revenue enablement will be turned on its head.

Today, most revenue enablement teams are seen as "content factory."

In three years?

They'll be respected as a *revenue risk management* team.

Here's why:

AI can quantify revenue skills you couldn't quantify before:

• Discovery
• Multi-threading
• Consensus building
• Business case development
• Mutual success plan execution

And literally 100s more skills across every GTM role.

AI can literally say things like:

"Zack is in the 67th percentile of enterprise discovery skills - here's the proof."

But here's where enablement earns their seat at the table:

Tying quantified skill improvements to revenue outcomes.

Because once you can objectively measure skills?

Now you can say things like this:

"Our team is only in the 33rd percentile of multi-threading skills, and according to our own data, that skill gap cost us $5.3 million closed-lost last quarter."

"If we grow our multi-threading skills to the 80th percentile, based on our pipeline, we project we'll close $2.1 million in incremental revenue."

That's not just power.

That's crack-cocaine for CROs, CEOs, and even boards.

This is why soon, Boards will ask for the revenue org's skill health the same way they ask for pipeline health.

Mark my words.

The revenue enablement profession will divide into winners and losers:

Winners accept revenue accountability. 
Because that's those who manage revenue risk do.

Losers deflect revenue accountability.
And wish they could hide behind a slide deck and no quota.

The choice will be yours.

But one thing will be clear:

Revenue enablement won't be able to hide from revenue accountability anymore.

And for the best of them, that's great news.

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

Performance Coach to Enterprise Sellers | I help you drop the mindset trash, and optimize your daily routines to eliminate procrastination | AI Obsessed | Favorite movie: Hunt for the Wilderpeople

I'm Amber, a Performance Coach dedicated to helping elite enterprise tech sellers break through their mental barriers, upgrade their habits, and skyrocket their success.

With over 800 paid coaching sessions under my belt, I’ve helped hundreds of top-performing sellers to exceed their quotas and reclaim control of their workdays. I understand the unique challenges faced by enterprise tech sellers. 

Having climbed from a blue-collar background to the fast-paced world of tech, I've experienced imposter syndrome firsthand.

I worked my way up to find myself living and working in downtown San Francisco for a unicorn tech startup. I felt like a major Imposter -- At any minute people would realize that a person with my background was not supposed to be there.

One of my favorite quotes is by Ricky Gervais: “The best advice I've ever received is, 'No one else knows what they're doing either.” If other people can make it up, we can too.

I came up with my own system for overcoming self doubt, and I’ve used it to help thousands of people overcome their own imposter syndrome and mindset junk.

It drives me nuts to see someone with massive potential standing in their own way. I’m obsessed with finding the right tactics that work for every different kind of person. There’s nothing more rewarding for me than seeing someone break through their barriers and realize what they’re capable of.


Outside of coaching, I enjoy:

🏊 Swimming
🚴 Mountain and road biking
🏃 Running
📽️ Documentaries - specifically about top performers
📚 Avid reader of non-fiction -- business and self-help
🏆 I’m a 2x State Champ:
💃 Once for Competition Dance (we won with a routine on Pogo Sticks!)
🎭 The other for the State Drama Competition - we won in Pantomime (professional hand talker)
👯 I love a good dance party
🎶 Constantly on the hunt for new music 
🧠 Diagnosed with ADHD later in life 
🤖 Obsessed with AI and the endless possibilities it brings


My personality:

✅ Strengths Finder: Woo, Developer, Empathy, Individualization, Competition

✅ StandOut: Provider, Advisor (I can intuitively see how someone feels, and I’m a wealth of information from experts)

✅ Kolbe A: 3-3-9-4 (Simplify, Adapt, Innovate, Restore)

✅ Myers Briggs: ENFP (Enthusiastic, Creative, and Sociable Free Spirit)

✅ Enneagram: 3 - The Achiever

Amber Deibert

I was just reflecting on a year of completely transforming my health.

The keys for me were:

Knowing myself (I need accountability, not online courses)
Giving myself permission to do it messy

A year ago, I had gotten into a regular rhythm of going to the gym (!!), and I was really proud of myself. 

I would wake up early every morning (something I thought I would NEVER - like really, NEVER - be able to do), and I would either run, swim, or bike. 

But then there was a part of me that wanted to learn to strength train, but I was terrified. 

(I avoided the weightlifting side of the gym).

Sometimes I would have to go through the weights side to get to the yoga room, and I felt SO UNCOMFORTABLE I wanted to crawl out of my skin. 

I felt like all these super ripped people were staring at me, and their eyes said, “what are you doing over here?! You obviously don’t belong!”

But I did really want to learn how to do it.  

I could have found a course to teach me, but I knew I wouldn't actually do it, so I had another option: working with a personal trainer at my gym. 

But come on, I’m not the kind of person who hires a personal trainer?! Sheesh, that’s got to be like millions of dollars, and who does that?? I’m not that kind of person. Plus, how embarrassing would it be to admit that you have no idea what you’re doing and make a complete fool of yourself IN FRONT of an expert?? Psh… yeah right. 

HOWEVER (judgy Amber, take note…), I also know about myself that the best way I can support my goals is with outside accountability. 

So in January last year, I bit the bullet and signed up to work with a personal trainer. I wanted someone to teach me how to lift, how to use the machines, and watch my form to make sure I didn’t break myself. (And I found that actually it was not MILLIONS of dollars…)

I committed to 6 months. 

Y’all… this is the best money I’ve ever spent in my entire life. 

Investing in a personal trainer CHANGED MY ENTIRE LIFE. 

Getting the knowledge I needed (straight from someone who was an expert!) accelerated my growth. 

Having that person to cheer me on kept me consistent, and everything I did was personalized to me and my goals (and weaknesses, ha!). 

I'm not joking when I say that this positively impacted every single area of my life. 

↳  my health improved (duh)
↳  my eating improved 
↳  my relationships improved 
↳  my parenting improved
↳  my professional life improved 
↳  I made more money than ever before 
↳  my confidence skyrocketed 

And now I’m obsessed with strength training. 

I can’t get enough of it. I crave it. 

I love showing myself what I can do. 

I feel so proud of myself. 

If you're staring down some personal change that you want to make, I hope this gives you hope. You can absolutely do it. 

Give yourself a lot of time, and a lot of understanding, and it's as good as done!

Sales Performance Speaker and Coach for Enterprise Sellers | Mindset & Productivity | Creator of the Work Like You Workout™ Framework for pain-free productivity 💪

I had a full circle moment at the gym this morning. 

It made me realize I’m so grateful to myself for letting myself be a sucky beginner. 

A year ago, I committed to learning how to strength train.

It was an awkward, uncomfortable process to learn how to strength train, but now I can't imagine my life without it!!

I love it so much!

So this morning I jumped on my old treadmill (after avoiding cardio for a year), and just had a moment. 

Holy moly.

I met myself from a year ago. Wow. 

That Amber would never believe who I am today. She honestly wouldn’t be able to process it.

I'm so grateful to myself for:

↳ being willing to look like an idiot
↳ being a sloppy beginner 
↳  betting on myself
↳  not quitting (even when it sucked and every muscle in my body was screaming at me)
↳  pushing through the self-doubt
↳  being brave enough to feel all the feelings 
↳  making the best financial investment of my life (hiring a personal trainer to coach me and keep me accountable!)
↳  knowing and accepting myself and setting myself up with the best possible chance at success (courses)

For those of you who aren’t sure if you can create your dream life and are feeling doubt, I hope this gives YOU some hope. 

For those of you who have been through a similar life transformation, LOOK AT WHAT YOU DID!!! Look how far you’ve come! Holy mother!! You’re doing it!

Be willing to feel stupid as a beginner. It’s just part of the process.

I got braces again last month.

Yes, again.
Yes, I’m vain.
And no, I did not have “adult braces as a mindset lesson” on my 2026 bingo card.

But it cracked something open for me in the best way.

Because the first time I had braces, I was a broke college kid working at Kinko’s… counting dollars… saying no to an $8 burrito because I literally didn’t have it.

But this time I paid for my son’s braces and mine upfront, and it barely registered.

And it hit me: we don’t feel successful when we become successful.

We only feel it when we stop long enough to notice the contrast.

Nothing is wrong with you.
You’re just measuring yourself with the wrong ruler.

Old Way vs New Way (how high performers measure success)

Old Way
↳ You measure your life by the gap (where you are vs where you “should” be)
↳ Comparison quietly erases your progress
↳ You chase “status” and call it ambition (and the finish line keeps moving)

New Way
↳ You measure your life by the gain (how far you’ve actually come)
↳ You choose goals based on values, not optics
↳ You ask one question before you chase the next thing:

“Would I still want this if no one could see it… and I couldn’t compare it to anyone else?”

That question will expose what’s aligned… and what’s just performance.

Keep going.
Just make sure you’re running toward what you want, not what looks impressive for 48 hours.

In this week’s episode, I break down:
↳ Why comparison makes even “successful” people feel behind
↳ The desert-island test that instantly reveals whether you want something for you or for status
How to use money (and achievement) as a tool, not a scoreboard

You can watch the full episode on YouTube (@amberdeibertcoaching) or listen on The Achievers Podcast or wherever you get your podcasts.

What’s something you’re proud of that your younger self would be absolutely blown away by?

If you have ADHD, it’s not that you don’t know what’s important. It’s that your brain is wired to follow what’s interesting.

I learned that:

Neurotypicals do what is IMPORTANT.

ADHDers do what is INTERESTING.

So, when you find yourself doing literally anything except the thing you “should” be doing?
↳  You’re not irresponsible.
↳  You’re not avoiding.
↳  Your brain is simply chasing stimulation.

This is absolutely solvable.

Once you understand your interest-driven brain, you can build systems that make the important things feel interesting, or at least doable.

I teach these techniques to my ADHD clients (and use them myself), and they’re game-changing for getting the high-value work done each day.

Want more ADHD-friendly productivity tools?
Subscribe to my weekly newsletter, Get Out of Your Own Way.
It’s where I share everything I can’t fit into a single post. {Link in comments}

Why ADHD Doesn’t Mean You’re “Bad at Focus”

The manager you work for has an outsized impact on how successful you can be.

When you have a manager that gives you the kind of support YOU need...

(which is totally different for each person!)

...you are naturally more successful.

Be REALLY selective when finding a new manager!

Here's what no one admits about pushing your comfort zone. 

I was just talking with a friend who recently created her own business after being in the corporate world for decades.

I was celebrating her, and she said something like, "I just hope I can build something great like what you've built."

It really made me reflect.

I told her, "The way things look on the outside is nothing like how they feel on the inside."

Whenever you're embarking on a big change like this, it feels horrible on the inside. 

There's so much imposter syndrome that comes up. So much self-doubt.

It's been fascinating to see how much that has continued even as I'm about to cross over eight years in business.

I feel confident and secure in my abilities and my skills, but I'm still pushing the edge of my comfort zone by learning new skills and evolving into new areas. 

So the imposter syndrome is always there.

I've been really buoyed up lately by hearing other entrepreneurs very candidly share their experiences. 

↳ Share that it's hard for them. 
↳ That they still question themselves. 
↳ That there are just as many challenges as there are successes.

So I want to echo that: having your own business is the most personal development I've ever done in my life. 

…and I am BIG into personal development.

It's so fun and so rewarding. 

And also, if you're embarking on a big challenge like this and feeling like you’re in way over your head, you are totally not alone.

I write about this kind of stuff regularly in my newsletter. Join me there if you want more honest conversations about the messy middle of growth.

If you’ve ever looked at the #1 rep and thought, “Must be nice… they probably don’t deal with this messy self-doubt thing”…

I need you to hear me: they do.

Nothing is wrong with you.
 You’re not “behind.” You’re just human.

Here’s the one mindset shift I see top performers use (and the one I coach into everyone):

Old Way vs New Way (when imposter syndrome hits)

Old Way:
You spiral inward.

↳ “Am I good enough?”
↳ “What if I blow this call?”
↳ “What if they can tell I’m winging it?”
↳ “I need this deal to close.”

New Way:
 You shift outward into service.

↳ “What is their real problem?”
↳ “What are they trying to protect right now?”
↳ “What would make this decision feel safe?”
↳ “How can I help them think clearly, whether they buy or not?”

Because insecurity is almost always a symptom of being stuck in your own head.

When you move into a consultative state (coach energy, not needy energy), a few things happen fast:

↳ You stop auditioning.
↳ You start leading.
↳ You sound calmer, clearer, more credible.
↳ And buyers feel it.

This is the same reason top reps can “detach from the outcome” and still close monster deals. They’re not robots. They’ve just trained themselves to redirect their attention.

In this week’s episode, I break down:
“I have a 100% track record of always figuring it out.” (Yes, steal that mantra.)
Plus, how the best sellers identify their weaknesses and build workarounds instead of trying to “fix” themselves.

You can watch the full episode on YouTube (@amberdeibertcoaching) or listen on The Achievers Podcast or wherever you get your podcasts.

When you’re feeling shaky on a deal, what do you usually do first: spiral inward… or shift into curiosity about the buyer?

I give up on being an entrepreneur.

Over and over again.

In fact, at least 1-2x per week, I’m ready to burn it all down.

I get convinced that it’s not working, and it’s never going to work.

…and then I just keep going.

And when the next day comes, things start working.

I start working.

Anything that’s worth pursuing will feel like crap 50% of the time.

And that’s normal.

Just keep going.

If you’re feeling overwhelmed, it’s probably not your workload.

It’s the lack of clarity.

When your brain’s trying to hold 100 priorities at once, you end up in reactive mode. Everything feels urgent. Nothing actually moves forward.

Here’s what works instead:

Plan your entire quarter in 12-week sprints.

That’s it. Here’s how I break it down:
↳ Choose 1-3 goals max
↳ Define what success looks like (lag vs. lead measures)
↳ Break goals into weekly tactics
↳ Assign tactics to specific weeks
↳Track them visually (I use color-coded sticker charts)

It gives your brain a break and your week a map.
No more waking up at 3 a.m., remembering that email you forgot to send.

In this week’s episode, I break down:
↳ How to use the 12-Week Year for quarterly planning
↳ The 2-minute rule that stops procrastination in its tracks
↳ The A/B/C + 1/2/3 prioritization method to calm chaos instantly 

Wait until you hear the simple tool that turns your chaotic to-do list into 5 crystal-clear priorities.

You can watch the full episode on YouTube (@amberdeibertcoaching) or listen on The Achievers Podcast or wherever you get your podcasts.

What’s your biggest struggle when it comes to planning?

Stanford researchers discovered something surprising about starting a new habit. 

Have you ever heard of tiny habits?

It's the idea that BJ Fogg and the Stanford Behavioral Science Lab came up with. 

The idea is to habit stack your habits and start TINY. 

Anything you want to add to your routine, you find another habit you can stack it after.

Let's say you want to do more exercise. 

You might decide that every time you turn on your shower, as you're waiting for it to heat up, you do one tiny habit. 

Something like doing one pushup.

Or after you brush your teeth, and you want to floss more, you floss one tooth. (Sounds silly, I know, but go with me here)

The idea is to make it so tiny that your brain is like, "Oh, I can do that." And continue to do the tiny habits until you get really good at it.

I tried this with a client. 

She was having a hard time doing her physical therapy exercises. 

(I mean, who doesn't?) 

And not only that, she was a busy mom of (many) small children.

We found a moment in her day. 

Every day, she cooked oatmeal in the microwave for herself. 

So we found that if she did her 30 seconds of core exercises while her oatmeal cooked, she could reliably do it every single day.

Otherwise, she was never able to find time for it in her busy schedule as a mom.

Stacking her oatmeal habit alongside her PT cued her brain to remember, and she got all her exercises done!

Try out tiny habits and see if they work for you.

A lot of you are feeling defeated about not keeping your New Year's Resolutions, but try finding a space in your existing routine to stack them together. 

And make them TINY! Tiny beats out “perfect but never done” every day!

Follow along if you want more simple, science-backed ideas for getting more done with less friction.

New Year’s resolutions? Total garbage.
They work for about 2% of people, and I’m guessing you’re not one of them.

Here’s what actually works for enterprise sellers who are ambitious and overwhelmed:

Instead of forcing motivation in January, plan your year around your natural cycles of energy and clarity.

Here’s how to start:

↳ Notice when you actually feel renewed (hint: it might be spring or fall)
↳ Visualize your life one year from now vividly, with all five senses
↳ Write it down like it’s already happened
↳ Let that be the roadmap. Not a punishment list.

Old Way: Set a goal to “fix” yourself
New Way: Do favors for your future self

In this week’s episode, I break down:

↳ Why New Year’s might be the worst time to set big goals
↳ The “future self” mindset that actually sticks
↳ A simple planning structure that works with your energy

You can watch the full episode on YouTube (@amberdeibertcoaching) or listen on The Achievers Podcast or wherever you get your podcasts.

When do you feel your strongest planning energy, in January or another season?

Sometimes sucking at your job can be really useful data. 

For my entire career, my employers LOVED me. ...until...

Anytime I decided to leave a company, my employers always begged me to stay. One time, even offering to DOUBLE my salary if I would stay.

So I had a belief that I was a great employee and employers loved me.

Until this one point.

I had just returned from maternity leave, my team had restructured while I was gone, and the company was undergoing a MASSIVE overhaul.

Suddenly, I wasn't getting the projects I wanted.
I wasn't getting the promotions I wanted.
I was actually sucking at my job.

I started to question everything:

Was I actually a good employee? Maybe I wasn't that great. Maybe I was delusional before. Did employers actually like me?

It was a massively low point in my career. I started to wonder if I had any real worth in the workforce.

And add on top of all of that the pressure of trying to navigate working as a new mom.

Here's what I discovered.

I was in the wrong environment.

It wasn't that I was wrong, and it wasn't that my employer was wrong. It just wasn't a good fit for either of us.

I wasn't an unsuccessful person. I was just in a situation where I could never thrive, no matter how much effort I put into it.

I got myself out of there, and I started to thrive again.

If you're feeling frustrated and stuck, try taking a look at your environment.

Is it a place where your strengths are being optimized, or is it an environment where you need to improve your weaknesses (a losing battle, if you ask me)?

This isn't about blaming or accusing anyone. It's just an honest look at what reality is.

Nurture wins over nature in the workforce.

If you're stuck wondering whether it's you or your situation, I'd love to help you sort it out. Reach out if you want to talk about working together.

Nature vs Nurture

"Ain't bad, just is."

The first time I heard Chris Dorris say this, I cracked up. 

(Who says "ain't" these days?)

But the more I've used it, the more I realize how brilliant it is.

Saying "ain't" in my mind or even out loud is such a pattern interrupt that it really helps me see the reality of what's happening.

Here's the concept: 

So many things we experience, we instantly judge as bad. 

Then we get emotional, dysregulated, frustrated, and feel stuck.

Chris talked about changing that whole perspective. 

Instead, see the situation as neutral.

Everything that happens to us is neutral. We get to decide if it's a good thing or a bad thing.

Another thing he says: "Your problem is that you experience reality problematically."

What you're experiencing is reality. If you have a problem with it, that's because you're experiencing it problematically.

Using "ain't bad, just is" has been so helpful to neutralize how I'm feeling vs. what I normally would do: judge the situation, feel frustrated, then try to fix the situation and fix my feelings.

When you can just detour that whole drama and energy waste and instead decide "ain't bad, just is"... maybe there is something good about this situation.

I ask myself, "What if this is the best thing that could happen?"

Or tell myself, "Maybe in the future I'll see how this was exactly what needed to happen."

It's so much less energy draining when you get to decide how you want to feel about it.

If you want to learn more about this, you’ve GOT to check out Chris’ book, Mental Toughness Mantras. It has legitimately changed my life!

In January of 2025, I set a goal to build self-trust. It felt impossible. 

And now it's been a year, and I could never have guessed how it would pan out.

I've had low self-trust for a long time. I frequently say I'm going to do something and frequently don't do that thing.

How can I ever trust myself if I don't actually do what I say I'm going to do? 

In January, it became very obvious that self-trust was exactly what I needed and exactly what was holding me back.

So I made it my goal for 2025 to build self-trust.

I laughed at myself for this goal. It felt completely impossible and totally ridiculous.

It's not like I hadn't tried before.

I had tried many times to be consistent, to do what I said I would do, to be able to trust myself...

And again, I failed every single time.

I was pretty gung-ho about it early in the year, and then I felt like I wasn't making any progress, so I pretty much gave up on the goal.

And now it's been a year, and I just saw a reminder for myself that I created at the beginning of the year of self-trust. 

Seeing that, I just realized that I have made massive improvements in trusting myself this year, but it didn't come how I thought it would come.

I thought it would come through:  
↳ Pure grit
↳ Pure consistency
↳ Massive discipline
↳ Never letting myself down
 
 It turns out none of those things are true.

What actually created self-trust was: 
↳  Massive self-acceptance
↳  Massive self-compassion
↳  And meeting myself where I am vs. trying to make myself be something I'm not 

I learned to support myself and give myself what I need (a lot more rest, frankly).

When I did that, I assumed my productivity would plummet.

But actually, I have been more productive than ever before.

I've gotten really clear on what are actual priorities and what are distractions.

And when I sit down to work, I get work done faster with more clarity and more focus because I am ready to work instead of grinding away operating at a 2 out of 10.

So, wildly enough, now I trust myself to get done what I need to get done (because I'm getting done what I need to get done).

But it wasn't through hustle or grind or forcing myself. It was through caring for myself.

CRAZY!!

Have you had a massive transformation last year? I'd love to hear about it!

Self-Trust

For 20+ years, I set the same goal every January: Get in shape.

I tried training plans, spreadsheets, triathlons, cardio streaks… and every time, I fell off the wagon. I’d beat myself up, tell myself I was lazy, and believe something was wrong with me.

But last year, everything changed.
I didn’t find a better plan.
I found a better approach.

OLD WAY:
↳ Rely on fear, guilt, and shame to push through
↳ Chase consistency through rigidity
↳ Use deadlines to force motivation

NEW WAY:
↳ Start with self-acceptance
↳ Make decisions based on what actually works for me
↳ Treat future-me with generosity

And here’s the wildest part:
It worked. Better than anything else ever has.
I'm now the most consistent I've ever been with fitness, and the benefits have spilled into every area of my life.

In this week’s episode, I break down:

↠ The surprising strategy that finally made it stick
↠ Why motivating yourself with fear leads to burnout
↠ How kindness can be your most powerful performance tool

You can watch the full episode on YouTube (@amberdeibertcoaching) or listen on The Achievers Podcast or wherever you get your podcasts. 

What’s one area where you’ve been pushing instead of partnering with yourself?

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