Chris Orlob

I joined Gong at $178k ARR six years ago. By the time I left, we were well beyond $200M and worth $7.2B.

I also had the good fortune of working closely with dozens of SaaS companies that went on to become $1B unicorns, given who our customers were.

Here are 9 things I noticed about SaaS companies that go onto become unicorns (plus many of the things we did at Gong):

1. They get ultra-clear on their ideal customer profile. It's so easy to try to sell to everyone. And it's so counterintuitive NOT to if you're trying to build a big company. Future unicorns find their sweet spot, plus their 2nd and 3rd 'tiers.'

2. They get ultra-clear on their ideal REP profile. Before they scale and add headcount, they know exactly WHAT they want in AEs (and what they don't). They live the wisdom that success in one context doesn't automatically transfer to another.

3. They build a 'semi-repeatable' sales process before scaling. Repeatability is a little bit of a misnomer when scaling: you're never perfectly 'there.' But the best SaaS companies get their playbook to 'good enough' before they scale. Otherwise, you'll add headcount that doesn't know wtf they're doing.

4. They build a repeatable hiring process. Their hiring processes are 'boring.' They do the same thing every time with every candidate. Which gives them a gift: pattern recognition, and a crazy ability to identify whether someone 'fits' their ideal rep profile.

5. They maintain a 3:1 pipeline coverage ratio. They watch this metric closely. If most reps don't have at least 3x pipeline against their number, there's fixing to do before scaling further.

6. They ensure 80% of their reps hit at least 80% of their number. Far below this? Again, you're got fixing to do in your go-to-market motion. Scaling will accelerate expense without accelerating revenue.

7. They maintain a CAC payback period of less than 12 months and a 3:1 LTV to CAC ratio. This really should have been #1, because it's an indicator that you're product/market fit is ready for scale (or at least, if you're not here, you're not yet ready to scale).

8. They build a structure new hire onboarding program. You can't just throw new AEs into a sink or swim environment. Again, expenses will far outdistance new income. Bring new reps through a rigorous, structured training program so they can produce new ARR on a predictable schedule.

9 They don't sacrifice their bar for talent in the name of hitting headcount targets. This is arguably the hardest one, because the temptation to soften is so great. Better to leave an open territory unfilled than to fill it with someone you'll have to backfill later (and could have a negative impact on your culture).


We put together a 'unicorn checklist' of the things we learned from these amazing SaaS companies (plus my experience growing Gong).

Want the 'Unicorn Checklist' for free?

Grab it here: https://lnkd.in/g9ssDdnC

Let me know if I missed anything crucial in the comments.

$100,000,000 in ARR.

That's how much revenue our first few “demo flows“ at Gong closed.

I partnered with our VP Sales designing these sales demos before we both passed the torch to someone else.

Here are 9 sales demo tips I learned through it all.


1. Show the most powerful feature FIRST.

Most SaaS sellers don't do this. They 'build up' in a 'ramp up' demo.

Wrong.

Flip it upside down and show the top feature upfront.

Let your buyer's head spin (in a good way).

Unpack from there.



2. Solve exactly.

Want an easy way to speed customer decision making?

Solve their pain on a 1:1 basis.

No more, no less.

Don't complicate it by showing all you've got.

“We can also...“ leads to overwhelmed buyers.



3. Catalyze a decision.

What's the point of a demo?

To inform? Educate?

Neither. It's to catalyze a decision.

What's the 'next' decision your buyer needs to make?

Agree on that before the demo.

Then, demo in the context of helping them make that decision:

“My goal is to get you so FIRED up about what we do that at the end, you're willing to sponsor a meeting with your CMO, or you tell me I missed the mark. Fair?“

Catalyze. Don't inform.



4. Frame the problem.

Summarize the buyer's challenge and impact before the demo.

Then validate it:

“Based on what you told me, you're going to LOVE this.“

Let your buyer know they're in the right place.



5. Orient them to the screen.

Most buyers 3 minutes into SaaS demos:

“WTF am I looking at?“

Before you click around, explain what they're seeing.

The confused mind says 'no.'



6. Spend 10s framing the pain a feature solves before showing it.

Remember how I said to frame the problem before the demo?

Do a mini version of that for each feature you show.

What's the pain it solves?

Spend 10s summarizing that.

THEN the feature will land with ease:

“Earlier you said xyz is a headache. Here's how we solve that.“



7. Tell a customer story after every key feature.

Want your buyer to think about your demo for days?

Tell a customer story after each click path.

“Here's how X customer is using that workflow to solve Y pain“

People remember stories and forget click paths.



8. Ask a question after every key feature.

Stop and have a conversation.

Here are a few questions to test:

- How does that compare to how you solve this today?
- To what degree is this resonating so far?
- To what extent do you see that solving x pain?
- What benefits do you see showing up in your world from that?


9. End your demo with “What excited you most about what you saw today?“

Transition to discussing next steps.

Hope these help you.


P.S.

I created an online course that teaches everything I learned about SaaS demos that closed $100,000,000 worth of SaaS.

Crush your SaaS demos (with 3,000 others) here:  https://lnkd.in/gMsskq3x

“We have budget for $199,000,“ the procurement manager spat at me. I had a $325,000 deal forecasted, and we had 7 days left to close it.

That was June, 2020.

End of quarter.

Egg about to be smeared all over my face.

I paced around my house while my family swam at the pool.

Cursing under my breath.

Back then, I knew every negotiation tactic in the book.

But that was the problem:

My negotiation “strategy“ was actually what I now call “random acts of tactics.“

A question here. A label there. Throw in a 'give to get.'

There was no system. No process.

Just grasping.

Since then, I now follow a step by step process for every negotiation.

Here's the first 4:


1. Summarize and Pass the Torch.

Key negotiation mistake.

Letting your buyer negotiate with nothing but price on their mind.

Instead:

Start the negotiation with this:

“As we get started, I thought I’d spend the first few minutes summarizing the key elements of our partnership so we’re all on the same page. Fair?”

Then spend the next 3-4 min summarizing:
- the customer's problem
- your (unique) solution
- the proposal

That cements the business value.

Reminds your counterpart what's at stake.

They might not admit it:

But it's now twice as hard for them to be price sensitive.

After summarizing, pass the torch:

“How do you think we land this plane from here?“

Asking questions puts you in control.

Now the onus is on them.

But you know what they're going to say next.


2. Get ALL Their Asks On the Table

Do this before RESPONDING to any “ask“ individually.

When you 'summarize and pass the torch,' usually they're going to make an ask.

“Discount 20% more and we land this plane!“

Some asks, you might want to agree to immediately.

Don't.

Get EVERY one of their asks on the table:

You need to see the forest for the trees.

“Let’s say we [found a way to resolve that]. In addition to that, what else is still standing in our way of moving forward?”

Repeat until their answer is:

“Nothing. We'd sign.“

Then confirm:

“So if we found a way to [agree on X, Y, Z], there is nothing else stopping us from moving forward together?“


3. Stack Rank

They probably just threw 3-4 asks at you.

Now say:

“How would you stack rank these from most important to least important?”

Force them to prioritize.

Now for the killer:


4. Uncover the Underlying Need(s)

Ignore what they're asking for.

Uncover WHY they're asking for it.

If you don't, you can't NEGOTIATE.

You can only BARTER.

You might be able to address the UNDERLYING need in a different, better way than what they're asking for.

After summarizing all of their 'requests,' say this:

“What’s going on in your world that’s driving you to need that?”

Do that for each one.

Problem-solve from there.

P.S. 24 sales training tips to double your sales team's win rates: https://lnkd.in/g_JF-ytC

I know a SaaS salesperson who made $350,000/year at age 26.

If you knew him at 19?

You'd guess that he'd be making $15 an hour:

- didn't finish his degree
- grew up in a broken home
- no role models growing up

But today?

Lives in The Marina with his Fiance with a view of the Golden Gate Bridge.

They spend their time:
- soaking in the beautiful Bay Area
- finding new hole in the wall restaurants
- walking their dog to the local coffee shop
- and of course, working hard and closing deals

He hasn't had a hint of money problems in years.

Once I asked him “What drives you?“

Expecting to hear “money,“ his answer surprised me:

“Evolution.“

“Tell me more...“ I said pretending not to be confused.

“I want evolve and grow. Making money's fun. But it's a byproduct of becoming someone valuable. And that's what really makes me tick.“

He sat silent then continued:

“I wouldn't run through walls for money. I *would* run through walls to become the person I'm capable of becoming.“

Therein lies the secret.

Acquire economically valuable skills?

And the economic value comes.

This salesperson was able to compress decades of income growth into a few short years.

And he attributes (almost) all of it to relentless skill acquisition.

Reading books.
Meeting with mentors.
Binging on podcasts.
Asking for coaching.

The gap between you and your dream life is not measured in time.

It's measured in skills.

Close the skill gaps your dreams demand, and you'll get to know what it feels like to compress decades into years.

P.S.

Take the first step and grow your selling skills by 1% in 60 min here: https://lnkd.in/g8mixtVc

Salespeople who want to be sales manager:

Here's what you need to know about getting promoted...

Promotions are not a reward for past performance.

They are a BET on future performance in a new, different role.

They are management's prediction of you.

Not their prize for you.

This is why it's less common to see high-performing, but unreliable prima donnas get promoted.

Unreliability ≠ management material.

Regardless of the 200% quota attainment.

It's not about what you've done (though that's table stakes to even play the game).

It's about what you will do.

When you understand that promotions are more about the future and that your past doesn't entitle you to them, you're one step closer.

Conduct yourself accordingly.

Opinion: 95% of the questions salespeople ask are worthless.

They don't create value for the buyer.

They don't create value for the seller.

They simply burn precious meeting time.

And these days... that meeting time is indeed PRECIOUS.

Both the buyer and seller walk out with little progress to show.

Sellers: You need to get to the heart of deal FASTER and CLEARER.

Then there are 5% of questions that create insane value.

If you could only ask 4 questions in a 1st discovery call, here they are.

(the order here matters intensely)


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

Easy enough.

Just enough to kickstart the conversation in the right direction.

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

But not enough by itself.

Customers will (almost) 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.

And spending money to solve the problem begins to look REAL good.


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

Ask this too early?

And the answers will be weak.

BUT...

If you ask this AFTER those first three questions...

Your customer now has the FULL CONTEXT of the problem top-of-mind.

And now... their answers to THIS question will be far, FAR richer.

Give those 4 questions (in order) a try.

Let me know how it goes?

P.S.

Want to grow your SaaS sales income, revenue, or attainment at breakneck speed alongside 3,000 other SaaS sellers?

Learn more here: https://lnkd.in/g5fsZNDk

Last week, a struggling account executive shared that she wanted to earn $350,000 a year in sales. “Best advice on how to get there?“ she asked. Here's the counterintuitive answer I gave:

Me: “Can I tell you a story?“

Her: “Sure can.“

Me: “Six years ago I went to dinner with the CEO of Gong. I asked him, how do you build a billion dollar company? That's a pretty complex question. He shouldn't have been able to answer that. It's too broad.“

Her: “Yeah...“

Me: “But somehow he had a great answer. Here's what he said:

“First, build a product so good that a weak sales team can sell it.

“Second, build a sales and marketing team so good they could sell a weak product. Do both, and you're on your way.“

Her: “Ok...“

Me: “It turns out the key to earning a wonderful income in sales is basically the same answer.“

Her: *listening*

Me: “First, join a company that has such an amazing product, you could sell it even if you weren't that good.

“Second, become so good at every aspect of selling, you could sell a weak product is you had to. Do both, and your path is set.“

In other words:

1. Sell a great product.
2. Relentlessly build your skills

I often see people obsess about the first one without the second.

They (rightly) believe that selling a great product is a ticket to a higher income.

Here's what they don't get:

These hot companies?

The ones with amazing products?

They don't hire people who don't have strong skills.

They have the pick of the litter on talent.

Overinvesting at becoming the best at what you do helps in two ways:

1. It unlocks the opportunity to begin with.
2. It helps you capitalize on the opportunity your given

Everything you want is truly on the other side of skill acquisition.

Becoming the best at what you do is criminally underrated.

You're not 'years' away from your dream life and income.

You're 'skills' away from your dream life and income.

Skills are the true measure of distance between:
- where you are today
- where you want to be

Acquire the skills your dream life demands, and it's yours for the taking.

P.S. Grow your SaaS selling skills to the next level here: https://lnkd.in/gWVp_Vxd

A rep tried to sell our company a $50,000 deal.

Their follow-up email killed it in ten seconds.

It was a wall of text stuffed with links.

Case studies here, a demo video there, a pricing page, a whitepaper.

I'm the buyer in this story.

I took one look and thought: not a chance I'm responding to this tonight.

Nate Nasralla has a name for it: link stacking.

And it's one of three things reps constantly mistake for a business case.

Mistake 1: The ROI calculator.

Plug in some numbers, out comes a return. The problem is that an ROI projection is a future maybe. A promise that hasn't happened, anchored to nothing the buyer feels today. There's no problem at the center of it.

Mistake 2: The microsite.

A slick page with case studies and product videos. Looks impressive, relates to nobody. If you could send the same page to a different account without changing a word, it isn't a business case. It's marketing collateral.

Mistake 3: The link-stacked email.

Here's the brutal part. The higher your reader sits in the org, the faster they delete it. Executives don't click through a stack of links to assemble your argument for you.

So what actually is a business case?

A document so specific to this account's problem, circumstances, and buying committee that it would be useless anywhere else.

One the champion helped build and can defend line by line when you're not in the room.

The test is simple.

If your "business case" survives being sent to another account, you don't have one yet.

What's the worst follow-up email you've ever received from a seller?

P.S. Building business cases that executives act on is one of the 11 skills in our research on closing bigger deals. Grab the report → https://lnkd.in/g63fcp2D

A VP of sales lost a competitive deal last week and told me what the buyer said on the way out:

"I've never seen two products look more identical. This decision came down to price."

They went with the cheaper competitor.

Here's what made it painful. I know that category well, and her product is genuinely better.

The buyer couldn't tell.

I call this the twin effect.

You can spot the difference between your product and your competitor's in about four seconds. So can a parent of identical twins, because they live with them every day.

A stranger on the street sees one face twice.

That's your buyer. You eat, sleep, and breathe your product. They've sat through maybe three demos across every vendor in the category combined, and we expect them to run the comparison for us.

The math keeps getting worse. Martech had around 150 providers in 2011. Today it's close to 10,000.

Product differentiation is dead.

What replaced it is the spreadsheet of death, where your buyer lines up every feature side by side and the whole evaluation spirals toward price.

You don't win that spreadsheet by being better.

You win by influencing what goes on it.

Buying criteria is just a shopping list of capabilities a buyer wants in a solution. Sometimes it's a formal document, and sometimes it just sits in their heads.

Your job is to get one or two items onto that list that only you can deliver.

That work starts in discovery, not in the bake-off. By the time they're building the spreadsheet, the criteria are locked, and whoever shaped their view of the root cause shaped the list.

The seller who influences the criteria never has to win the feature war.

They designed it.

P.S. Here are the 11 skills your AEs must master to close enterprise deals: https://lnkd.in/g63fcp2D

Becoming a millionaire in tech sales before age 35 is “easy.”

Here are the literal steps:

1) Spend 5 years relentlessly mastering the craft.

2) Work seriously hard. Not workaholic levels. But hard.

3) Start earning $300K / year. See steps 1 and 2.

4) Maintain a $5,000 / month burn rate.

4) You should be able to invest $10,000 per month now.

5) Do this for 72 months with an 11% annual return, and:

6) You hit $1,000,000 in net worth.

That’s 11 years from a cold start to becoming a millionaire.

Few careers can do that.

I know many who did it by their early and mid 30s.

I did it before 30.

Yet few will do it.

Mastering your craft for 5 years straight is not fun.

Delaying lifetime inflation a decade ahead of your friends is not fun.

But you know what is fun?

Earned freedom.

P.S. By “easy,” I mean more an act of will than intellect.

P.P.S. 11 skills you'll need to master the craft on your way to $1M: https://lnkd.in/g63fcp2D

Hey salespeople: Don’t negotiate price until you know you're the vendor of choice.

Here's the trap:

You're still in a bake-off.

The buyer hasn't picked anyone.

And they start haggling with you on price.

It feels like progress. It's actually the opening move of a race to the bottom, because they're pitting you against your competitor, and the winner of that particular game is whoever gives away the most.

So when price comes up before you've won, stop and say this:

"Let’s assume we landed on a price you felt was fair. What would still have to happen before we move forward together?”"

If the answer isn’t “Nothing, we’d move forward”?

You have selling to do. Not negotiating.

If they say it’s still down to you and one of your competitors, ask this:

"If price were not an issue at all, who would you move forward with?"

If they say you, game on.

You now have permission to negotiate, if the spirit moves you.

If they say no, you can negotiate until you’re blue in the face.

But you’re still not winning.

It is the last step in a deal.

Win preference first.

Then talk about price.

P.S. Here are the 11 skills your AEs must master to close enterprise deals: https://lnkd.in/gdreD-_Y

Kyle Coleman rose from SDR to CMO faster than anyone I know.

• Started as an SDR at Looker
• Scaled the SDR org to 65+ people
• Joined Clari and soon became CMO
• Recruited to Copy.ai as CMO and exited

Now he has one of the top jobs in tech:

Global VP Marketing at ClickUp.

His secret? POV-led outbound. Quite literally the *only* form of outbound that will always work, no matter what other tactics get stale and overused.

Last week I did a 60 minute deep dive with Kyle on The Caliber Show.

Today, that episode went live.

Learn Kyle's outbound-led POV strategy here: https://lnkd.in/gEgEYdmb

@Tag an SDR, AE, or seller in the comments who might like this.

Salespeople: If you are getting a "we can just build this with Claude" during your demo, you're cooked.

The answer is not a better objection handle.

If you're "handling" that objection?

Again: cooked.

The answer:

Sell a world view before you sell the demo.

Old Way vs. New Way.

Sell a point of view.

Demo to bring that POV to life.

Prevent the objection from entering their mind.

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).

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. Next week, I'm running a live masterclass - The Economic Buyer Selling System™: https://lnkd.in/g2ed-YPN

The goal?

Help you earn your next $100K commission check.

Because if that's what you want?

Mastering the art of selling to the Economic Buyer is non optional.

Master it here: https://lnkd.in/g2ed-YPN