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Shift Happens with Chris Ortolano (PLG)

Technology moves fast.

To beat it?

You have to be even faster.

Before it was all Marketing to Inbound Lead Conversion.

Today it's all about Product Led Growth, otherwise known as PLG.

It all started with a Slack message in 2020

I joined Tenbound back in November 2019 as a Full-Cycle Research Sales Account Executive.

It was then and there that I knew nothing about how SaaS and tech startups work.

Series A, Series B, Series C.

Series What..?

Million dollars funding?

Tell me more!

“Hey Jax, congrats on the new role with Tenbound, I’m running a series called Shift Happens and was wondering if you’d be open to attending?”

Absolutely!” I said without a doubt.

I mean c'mon, this guy's been in the game since 2012 and was a Sales Enablement Manager for DiscoverOrg.

He delivered over 10+ Sales Development training courses to the Enterprise SaaS Sales Team on best practices and GTM Strategies.

"He's bound to know a thing or two," I told myself.

Little did I know it was him that turned me into the Top Funnel GTM Strategist I am today.

Meet Chris Ortolano, previously Founder and Principal Consultant of Outbound Edge, a B2B SaaS consulting agency for early staged startups, Community Leader of, and now Product-Led Growth (PLG) Strategist.


One of my favorite episodes was on May 27th, 2020 episode "Putting People First".

We'll start by asking: 👉 What are you doing to stay resilient?

👉 What are you doing to build a resilient team?

👉 How does your personal experience GUIDE you at work?

👉 How can you create feedback loops to achieve peak potential?

He had the hard hitters in the space such as:

You can watch the replay here.

I knew I wanted to ask him to mentor me, but I believe before you can go for an ask you must become a person of value.

I attended just about all the full episodes and documented (about 5-6 in total) all the critical show notes and reported back to him as a "free" gesture.

Chris, Jack is my Life and Sales Coach but I need a second for the Start-up phase, will you take me under your wing?

"Yes," he responded, but under one condition.

"What's that?" I asked.

"You need to be very analytical, strategic, innovative, and have a keen eye for spotting patterns and trends".

"Consider it done!" I said.

Right off the bat since then, every chance I get I started to collect resources and data.

Obsessed and Ambitious with a Burning Desire to Succeed, I immediately started collecting as much data and resources as possible and started studying.

Here are a few learning outcomes I was able to spot early on in 2020.

  • Every SDR/BDR team with a total combined team of 10+ reps or so is known as a Power House

  • SDR Managers should have no more than 9 reps per manager

  • Reps average ramp time is "3" months but doesn't truly ramp until the 6th+

  • The common choice of sales tech is (if you even have the budget for it!):

  1. SFDC (CRM)

  2. LinkedIn Sales Navigator (Lead Builder)

  3. Zoominfo (Lead Enrichment)

  4. Outreach/Salesloft (Sales Engagement)

and as for the "best" SDR Leaders out there, they don't do it for the money.

They do it to watch the reps grow.

It's amazing to say, I've always had a hard time studying in school yet here I am in Sales Development studying my ass off.

It was then and there I knew it was my calling.


Since working at Tenbound, I was able to drive and close Net New Logos such as Drift, Vidyard, Captivate IQ, Social Chorus, and more.

You may be wondering how I did it.

Well, if there's one thing I can say and it was thanks to Chris's deep dive discovery framework along with having a vision board.

Habakkuk 2:2 King James Version

And the Lord answered me, and said, Write the vision, and make it plain upon tables, that he may run that readeth it.

Jax, I'm going to introduce you to a questioner that's going to change your life and it's called "The 5 Why's"

So what are The 5 Whys you ask?

Well, we all have our own Sales Methodologies and Philosophy we live by such as MEDDICC, Challenger, Spin Selling, Sandler, Gap, etc., but here's how we can executive on a deeper level.

  1. What's the problem here?

  2. Why is it a problem?

  3. What's the desired outcome?

  4. Who's responsible for solving the problem?

  5. What other problems are there?

The key here is to keep the spotlight shining on our prospects otherwise known as "Deep Discovery".

Imagine watching a Broadway show in New York City, what happens when the main character is on the scene?

The spotlight stays on them.

By taking the 80/20 rule your job is to ask open-ended questions where the person can not answer with a "yes" or "no", you STFU and listen.

If done correctly, you should be able to either qualify in or qualify out.

Not everyone does this due to unethical practices, but the balls are in your court.

As a Sales Professional, I truly believe how you do anything is how you do everything and for damn sure you can say your reputation comes with it.

Risk it at your expense.


Fast forwarding in time, it took me a year and a half to truly understand and get that "ah-ha" when it comes to being technical.

"Jax, good job on learning how to do deep discovery, now it's time to get your PHD in Sales Development; are you ready?"

So, if you want to be a Top Funnel Sales Dev. Strategist, you need to understand three things and they're as followed:

  1. Domain Knowledge

  2. Business Acumen

  3. Buyer's Journey

Domain knowledge is having a true understanding of how things work.

You're now an industry expert and you can "speak" your prospect's language.

Business Acumen?

Oh man, this is where the challenge lies.

It's the "Why" behind why they do what they do.

A good list of questions I picked up from Jim Qwik when putting yourself in their shoes is to ask yourself:

  1. Will I use this?

  2. How will I use this?

  3. Why must I use this?

  4. When should I use this?

These can be also known as Business Drivers or Business Cases.

Last but not least, is the Buyer's Journey.

What can you do in your line of work to create a parallel line let alone experience when it comes from beginning to end?

Whether it's from a point of entry through Marketing Qualified Lead, Inbound or Outbound Activities, and now Product-Led-Growth otherwise known as PLG.

It's your job to drive the buyer's journey in a parallel line and that's the challenge.

Anybody can tell you what to do, but it's all in the execution of how you do it.


Product Led Growth, what's all this buzzword all about?

Well, it's the new era of buyers vs sellers.

It's the "Try" before you "Buy".

Imagine you're at a shoe store shopping for a new pair of shoes.

You know what kind you want, brand and size.

Yet you still want to "try" them on before making a purchase decision.


According to Chris, when it comes to PLG there are two thing's to keep top of mind:

  • Qualitative Data

  • Quantitative Data

Qualitative Data is the "Why" behind the signup.

Quantitative Data is the "What".

Track, Measure, Guide, Scale, Repeat.

To Sell is to Fail, to Guide is to Slide.

The key is to develop the people, then the process, then scale. Too often it's the other way around. -Chris Ortolano

Here's a brief example, let's say we own a fancy steakhouse restaurant.


Scenario 1:

A customer comes in and says "I want A, B, and C".

Boom, that's it.

That's the order.

That's the bill.

That's the tip.

That's the Revenue.

Scenario 2:

A customer walks in and immediately gets greeted, properly seated, properly introduced, and asked a few series of questions.

Hi Mr. Customer, thanks for coming to Ortolano's Steakhouse.

My name is Jax and I'll be at your service today, have you been here before, or is it your first time?

Great, what do you typically like to eat?

Are you gluten-free or vegan?

Then the customer starts to ask "What do you recommend?" and this is where the game changes.

Well, based on what you told me here's what I'd recommend and why

  1. Steak

  2. Potatoes

  3. Cheese

What are your thoughts?


You see, when somebody is already in your store it's now best to Guide than to Sell.

This is known as "Sales Assist".

I get it, you're probably saying "Jax, this is software though not food".

Well, here's what an example would look like and all it takes is just a little itty bitty bit of research.

"Hi {{name}}, thanks for signing up for ABC.

Noticed you're in the 123 Industry, typically other {{title}} in the space such as yourself found using XYZ is most beneficial to their line of work.

Was this helpful at all..?"

So, you wanna win in Sales Development?

Keep the Buyer's Journey in a Parallel Line.

Like my mentor, Chris always says "Sales-Assist puts the People in Product-Led Growth".

To learn more about PLG, please reach out to Chris directly below.


Dear Chris,

You took me directly under your wing, with eyes in the skies and ears with no fear,

Not only did you help guide and challenged me to always push harder but you've turned me into the Top Funnel GTM Strategist that I am today.

Because of you, I'm now highly technical.

Because of you, I'm now highly practical.

Because of you, I'm now officially a Top Funnel Sales Dev. Strategist.

From the bottom of my heart, thank you for all you've done and I mean it sincerely.

With your PLG Strategy and my Top Funnel Expertise, I can't wait to see what the future holds for us!




Portland, OR


Portland, OR


(Bain Bridge Island, WA)


Connect with Chris:

Hear his "5 Why's" here on the 1UP Revenue Podcast



If you're in sales and really hate "admin" days, sign up for Scratchpad and try it out.

It's new.

It's free.

It's effective.

and if you still need some help, reach out directly to my boy Julian Ivan.

He'll guide you all the way.

Oh yeah, almost forgot.

It's also PLG.

#sales #salesdevelopment #PLG #productled

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