Ron Masi - Linkedin

Ron spent 10 years selling ink on paper before moving into SaaS in 2015. He built his enterprise game the hard way — through coaches, mentors, and a lot of swing-and-miss — until he had a system for running deals at a level most AEs never reach.

This episode is about a deal he's never forgotten. Not because of the size, but because of the execution. Every piece moved on purpose. The research, the internal alignment, the mind maps, the 90-minute demo that didn't show a single feature — it all came together and they walked out knowing they'd won.

What you'll take away:

How to build a deal dossier that actually changes how you sell, how to run an internal team across a complex opportunity without being in every room, and what it looks like when a demo stops being a demo and becomes a story.

On research:

"We highlighted every page of the CEO's book. We knew everything about them first."

On internal selling:

"Some people want to run really fast with you. Some people want to go slow. You have to think about how you're going to set this up."

On not connecting the dots for the customer:

"Never let the customer have to connect the dots. You need to connect them as much as possible."

On the demo:

"We didn't show the platform. We told them a story. We maybe clicked on four things. Maybe."

On the win:

"There was no possible way the people coming next were going to do that."

On the feeling:

"It's like an energy you don't even understand. Like if you played sports and you're in the zone — the basket was as big as the ocean."

People Mentioned:

• Jamal Reimer — Mega deal coach, mentor to Ron
• Brian Burns — Sales coach, introduced Ron to mind mapping & "map to money"
• Dennis Sorensen — Mentor, taught Ron how to unpack annual reports & 10-Ks
• Mind mapping — Core tool Ron used to organize deal strategy and move pieces as the deal evolved

Scott Knights — Major Account Manager at Proofpoint
The Episode
Scott Knights is a Major Account Manager at Proofpoint in Melbourne, managing some of the company's largest enterprise accounts across ANZ.

This episode centers on how Scott inherited an account where the platform was "just working" — a comfortable situation that most AEs leave alone — and turned it into a full-scale platform transformation by convincing 30+ stakeholders across a parent organization to adopt a new vision for human-centric security.

The account had been running the same Proofpoint deployment since the mid-2010s, nearly a decade without strategic evolution. You'll walk away with a clear picture of how to re-enter a dormant account, build a vision-led business case, and orchestrate internal and external stakeholders without losing anyone along the way.
Key Quotes:
On the most dangerous thing a customer can tell you:

"The first bit of feedback was, hey, everything's great, but there's not really any further opportunity here. And that's kind of really interesting because I think that's the place that AI cannot disrupt."

On qualifying out before the customer falls in love with the solution:

"I said, look, we can definitely solve this. But it's going to cost approximately X. Are you comfortable and confident that your executive or senior leadership are going to sign off on this? And in the end, you could sort of see that that particular individual hadn't kind of really thought through the commercial value of what they were trying to achieve."

On what the job actually is:

"It's as much of a orchestrator as it is as a technology evangelist. If I look at one of my customers, there's 30 odd stakeholders within the parent org — from security and strategy and architectural teams, through to operational teams, through to legal and vendor managers and procurement."

On the culture that quietly kills deals:

"If the culture between teams kind of goes a bit off and starts to become even a little bit dysfunctional — people getting agitated with one another, blame or frustration being vented on calls — the wheels can very quickly fall off after that."

On what to do when a stakeholder pushes back:

"Seek first to understand and then be understood. What's going on for that person? What's the concern? What's the gap they're trying to solve for? And then once I understand that, I can go, okay, well, how do we solve this together?"

On the mindset behind everything:

"I'm just a very average guy. There is nothing exceptional about who I am or what I bring. But it's determination or diligence or just putting in that little bit of effort every day — it adds up. The success is just a natural outcome of that value creation."
Referenced in the episode:

Strategic Coach — Dan Sullivan's entrepreneurial mindset framework; Scott studies his work extensively — strategiccoach.com

Eat That Frog! — Brian Tracy — tackling your single most important task first; Scott keeps this on his desk

The Dip — Seth Godin — when to push through hard seasons and when to move on

Books by Kazuo Inamori — Founder of Kyocera; philosophy of asking "what is the right thing to do as a human being?" in every business decision; most titles in Japanese, English translations available

Servant Leadership — Robert K. Greenleaf — Scott's explicit North Star for how he approaches customer relationships

Enterprise Sales Community — Founded by Jamal Reimer; global network of senior enterprise sellers — referenced as transformative to his own career

Connect with Scott:
LinkedIn — Scott Knights, Major Account Manager, Proofpoint, Melbourne

Episode Speaker Notes:
Merel Roest — Head of Sales at Guardey, Founder @ Blackbird GTM
The Episode:
Merel Roest spent her first five years in marketing before moving into enterprise sales — and that background became her edge. At Freshworks, she closed a three-year, group-wide customer service transformation deal with a 5,000+ employee American organization, selling a product that wasn't fully built yet.
Getting to yes meant running two parallel sales motions at the same time: one across multiple client stakeholders all the way up to their CEO, and one internally — working level by level through a hierarchical American HQ she could barely get face time with from her satellite office in the Netherlands. She won both.
Now Head of Sales at Guardey, Merel is building the sales org from the ground up — rewriting the pitch, cleaning the CRM data, and using custom-built GPTs to accelerate her team's learning curve.

What you'll take away:

How to build a deal story that actually lands, how to run an internal sale when the product isn't ready, and what it really takes to go from President's Club rep to first-time leader.

Key Quotes
On ditching the standard deck:
"It was me talking at you, not me talking with you. I shaped it completely around them — about solving their problem, not about us."On demos that keep people awake:
"A lot of account executives click through buttons. That's where people fall asleep. We created personas — this is your customer, this is their problem, this is how they'd use the tool."On the most powerful moment in any demo:
"Based on what you've now seen, how would this help you? Let them say it."On social proof that actually works:
"Everyone has a logo slide called 'Our Customers.' I hate it — it says nothing. What problem did you solve for them? That's the story you should focus on."On conviction in the deal:
"I already knew from my gut from the beginning — I don't know why, but I just felt it. This one's ours."On product belief as a prerequisite:
"I would never be able to sell something I don't feel is actually going to help. Your product needs to be good."On the internal sale:
"I didn't just have a pitch deck for the customer. I had a pitch deck for our internal stakeholders — one for my line of reporting, one for the solution engineers. Everyone needs to know the ins and outs of why we think this could work."On sales culture:
"If your employees are happy, your customers are going to be happy. Culture is very underestimated in high-pressure SaaS sales environments."On moving from rep to manager:
"I wanted to earn this person's respect before going into coaching mode. And I told him: I'm going to make mistakes. If I do something that doesn't sit well with you, I hope you'll tell me."On perfectionism at a startup:
"Done is better than perfect. I have to tell myself that every single day."

Resources & Links

Referenced in the episode:

• Winning by Design — Jaco van der Kooij's demo methodology; Merel cites his video on keeping buyers engaged throughout a demo
• The Maverick Selling Method — Brian Burns — top performers throw out the standard script
• SPIN Selling, MEDDIC, SPICED — frameworks Merel used to build custom GPTs for her team's discovery and coaching
• TrustPilot & Google Reviews — used by Merel to benchmark client performance and build compelling before/after storytelling
• Glassdoor — recommended for vetting a company's culture before accepting a role

Connect with Merel:
⁠LinkedIn — Merel Roest⁠