Exclusive event: How I scaled Gong to $200M w/ guest Chris Orlob

Join me, Chris Orlob, and James Fyfe on 24th Match, 9 AM Pacific for a live session on the discovery framework that helped me scale Gong to $200M ARR. Save my seat → register here

In this session, you'll learn:

• How to read your buyer from their opening words, and what to ask at each stage
• Why most reps pitch too early, and the specific questions that get to the real problem
• The one question that turned a $20K deal into $433K
• How to build urgency without pressure, because the buyer feels the gap themselves
• Real call teardowns from ZoomInfo, Numerator, Gartner, and LinkedIn

About me

I joined Gong at $200K ARR, helped scale to $200M and a $7.2B valuation, and debriefed thousands of real sales calls.

Since Gong, I've trained 11,000+ salespeople through pclub.io, with results like 245% quota at ZoomInfo, $433K from a $20K budget at Numerator, and Top 1% at LinkedIn.

So, about the event...

Ever lost a deal you thought was in the bag?

The buyer was engaged, asked the right questions, seemed ready to move. Then they disappeared.

Nine times out of ten, that deal died in discovery. Not at the proposal stage. Not in the negotiation. In the first real conversation, when the questions didn't go deep enough.

When discovery is off, everything downstream breaks. Proposals miss the mark. Quotes go out too early. Deals stall for reasons nobody can quite pin down. If you're running a sales team on HubSpot (or any modern stack), you've probably felt this. Even with your workflows running smoothly, inconsistent discovery means inconsistent results.

We see this every day at Portant. Even teams with their document automation humming (quotes, proposals, and contracts firing from HubSpot automatically) still lose deals when that first conversation doesn't reach the real problem.

So we're hosting a free webinar with me on the discovery framework that's helped 11,000+ salespeople fix exactly this. Below, I'll walk through the core ideas behind my approach, why it works, and what you'll get from the session.

The person behind the methodology

I joined Gong when it was doing $200K ARR. Over the next five and a half years, I helped scale it to $200M ARR and a $7.2B valuation, and became Gong's first seven-figure income earner.

What makes my path unusual isn't just the numbers. It's how I got there. I spent years systematically debriefing thousands of real sales calls to understand, at a granular level, what separates reps who close consistently from those who have good months and bad months.

Since leaving Gong, I founded pclub.io and have trained more than 11,000 salespeople in my discovery methodology. These aren't people learning theory. They're working reps with real results:

• ‍Christian Allen (ZoomInfo AE): 245% of target‍
• Brian Robak (Numerator): turned a $20K budget into a $433K closed deal in under 90 days, hit 131% of annual quota within seven months, and became the #1 mid-market seller at his company‍
• Jasi Johnson (Gartner AE): 152% of target‍
• David Rosenstein (LinkedIn AE): Top 1% "Club One"

The through-line across all of them: consistent, deep discovery.

The framework (the short version)

My approach isn't about asking more questions. It's about asking the right questions in the right order, based on where your buyer actually is.

I break it into four core moves:

1. Read the buyer's language

Your buyer's opening words tell you where they are. I teach three stages:

1. If they say "Something in your email caught my eye but I can't remember what", that's latent pain. They barely know they have a problem. Push them towards a demo now and you'll lose them.
2. If they say "We're struggling with X", that's active pain. They know the problem but haven't started looking for a fix.
3. If they say "We're evaluating platforms that do X, Y, and Z", they're already comparing options.

Each stage needs a completely different opening move. Most reps use the same approach regardless, and that's where inconsistency starts.

2. Separate symptoms from problems

Most reps hear a pain point and immediately start pitching. I call this "hammer and nail syndrome," and it permanently caps your income.

Here's why: buyers usually share symptoms, not problems. "We need visibility into our sales conversations" is a symptom. What that symptom leads to: 9-month sales cycles, a stretched cash position, a dilutive fundraise. Those are problems.

The difference matters because symptoms don't get budget approved. Problems do.

3. Go deeper

Once you've heard the initial pain, resist the urge to pitch. Ask what's driving it to be a priority right now. Then keep asking.

I have a specific question for this: "What's going on in your business that's driving you to prioritize this?"

Buyers often pause when they hear it, because they're thinking about the uncomfortable thing they've been putting off.

This is exactly what happened in the Brian Robak deal. A VP of Marketing at Numerator came in with a narrow scope: $20K, a small project. Brian asked the question. Kept going. And uncovered a CEO-level mandate about reclaiming market share that nobody had connected to this conversation yet. The deal went from $20K to $433K. Same buyer. Same first call.

4. Turn the conversation to the future

After summarising the buyer's current pain (better than they could articulate it themselves), I teach a pivot:

"Imagine we started working together today. Fast forward 365 days. What would have to be true for you to feel good about the progress we've made?"

This creates contrast between where the buyer is now (painful) and where they want to be (compelling), and that contrast is what real value selling runs on.

Why this matters for your whole deal cycle

Great discovery doesn't just improve your first call. It compounds.

When you uncover the real problem (not the symptom), your demo gets sharper: you know exactly what to show. Your proposal lands: it speaks to the buyer's actual priority, not a surface-level wish list. Your business case builds itself: you've already found the numbers that matter to the CFO. And your close rate goes up, because the buyer feels genuinely understood, not pitched at.

At Portant, we sit at the other end of this. We take what you learn in discovery and turn it into a quote, proposal, or contract from HubSpot in seconds. Accurate, branded, and ready for signature. We've automated over 5 million documents for 920,000+ users.

But we'll be the first to say: the fastest proposal won't save a deal that was poorly qualified.

Great discovery feeds great documents. Great documents close great deals.

That's why we're hosting this webinar.

What you'll get from the session

I'm running a 45–60 minute deep dive. Not a panel, not a surface-level overview. I'll cover:

• How to read where your buyer is from their language, and what to do differently at each stage
• Why most reps stop at symptoms, and the specific questions that get you to the real problem
• The "Go Back In Time" technique for buyers who want to skip straight to a demo
• How to go deeper and build a business case a CFO would actually approve
• The future-state question that creates emotional contrast and drives urgency
• Real call breakdowns, including the full Brian Robak case study ($20K → $433K)

Plus 10–15 minutes of live Q&A.

Who this is for

B2B sales professionals (SDRs, AEs, Sales Managers) who are serious about improving their discovery and tired of inconsistent months. If you're using HubSpot (or any modern sales stack) and want a repeatable system for qualifying harder and closing faster, this is the session.

Register for the free session →

And if your discovery is already strong but your quotes, proposals, and contracts are still the bottleneck? That's what we do. Beautiful, automated sales documents from HubSpot, done in one click. Start free here