Michael Scott is an Enterprise AE at Neara — a physics-enabled digital twin for power utilities — managing a book of exactly five accounts. This episode centers on how he closed a $5M+ enterprise contract with a utility that had just lost over $2 billion in market cap following a wildfire.

Michael had never sold a deal this size before, had two weeks to build his POV, and walked in having just read Jamal Reimer's book cover to cover twice. You'll walk away with the exact sequence — POV construction, POC, business case, consultant alignment, curated customer events, and deal structuring — that took this from a cold account to a signed $5M contract with a mega-deal still in process.

• Whyzer.ai — Jamal Reimer's AI-powered tool. Aggregates earnings calls, 10-Ks, and account intel into audio briefings. — whyzer.ai

• Jamal Reimer — Enterprise sales strategist, creator of the Two Mountain Model and Whyzer.ai. Previous guest on HTDWD.
• Brandon Fluharty — Sales and life design thought leader. Work focuses on avoiding the hedonic treadmill in high-income sales careers. Upcoming guest on HTDWD.
• Rob Cook — "Personal CFO for high income earners." Helps enterprise sellers with financial planning and keeping more of what they close.
• Sarah Thomas — Enterprise AE at Verkada (IoT security). Upcoming guest on HTDWD.

• Two Mountain Model — Get high in the account fast with an executive POV while running lower-level conversations for ground-truth intel simultaneously.
• Commission Breath — The moment a seller gets attached to the outcome. Kills negotiating power and the buyer can smell it.
• Race to Second — Utilities won't be first and won't be left behind. The trigger is seeing a peer already doing it.
• Short-Form Contract — A procurement mechanism common in utilities allowing work to begin while the full enterprise contract processes. Used here for a $5M+ engagement with a six-month shelf life.

Connect with Michael
https://www.linkedin.com/in/michaelscottco/— Michael Scott, MBA — Enterprise Account Executive, Nira (Search "Michael Scott MBA" to find the right one)

About the Show
How the Deal Was Done goes deep into the mindset, strategies, and day-to-day realities of world-class enterprise sellers and founders. Every episode centers on a specific deal — what happened, how it happened, and what other sellers can take from it.
Host: Matthew Klingner Audience: Senior AEs, Founders, GTM Leaders, and Enterprise Sales Professionals
© How the Deal Was Done Podcast

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

Mike Sullivan is Executive Director of Sales at TriNetX, where he sells into top-20 pharmaceutical companies.

This episode centers on his career-defining deal - a $3.55M ARR, two-year enterprise contract with a Fortune 500 pharma company that took nearly two years to close, ran 20+ use cases across 5 business units, and required Mike to get high in the account at month 20 of 24.

This came at a time of great personal challenge and difficulty - balancing debt and obligations, while threading the needle of an incredibly difficult strategic sale.

This deal flies in the face of almost everything we're taught in enterprise sales — and it worked because Mike refused to take shortcuts. He was 39 years old with $80K in debt when he joined TriNetX. This deal changed everything.

Connect with Mike:

• LinkedIn: ⁠Mike Sullivan⁠
• Website: ⁠mikesullivan.co⁠
• Mike offers free 30-minute coffee chats for anyone navigating sales challenges or working to turn things around — reach out directly on LinkedIn or via his site.

On getting high in the account:

"I wasn't high in this deal until month 20 of 24. That goes against everything we're taught in enterprise sales — but I couldn't get there no matter what I tried."

On running the pilot:

"Rather than you as the customer pointing and clicking, we ran the use cases in our software for you and presented back the output. We did the upfront heavy lifting ourselves."

On co-creating the business case:

"We were building the business case with the customer throughout the entire deal cycle. So when we had the readout meeting, it was crystal clear — here's where you are today, here's what tomorrow looks like."

On commission breath:

"If you're making it about you and your commission check, you're putting your deal at risk. You'll subconsciously say the wrong thing at the wrong time."

On patience:

"Aggressive patience. You've got to be aggressive in the right way — persistent, following up — but patient as hell. If you squeeze an egg too hard, it breaks."

On the internal sale:

"A lot of times the internal sale is harder than the external sale. We know in our gut which deals have huge potential even when the pipeline doesn't reflect it."

On transformation:

"I didn't feel like I was selling at all during that deal cycle. It was more just project management — co-creating the process, co-creating the business case, really partnering with them."

On mindset:

"It's you against you. Are you doing the best you can do every single day? You can only control your attitude, your actions, and your effort. Literally nothing else."

Books mentioned:

• The Gap and the Gain — Dan Sullivan & Dr. Benjamin Hardy
• The Four Agreements — Don Miguel Ruiz
• Ego Is the Enemy — Ryan Holiday
• Take the Stairs — Rory Vaden

Connect with Mike:

• LinkedIn: Mike Sullivan
• Website: mikesullivan.co
• Mike offers free 30-minute coffee chats for anyone navigating sales challenges or working to turn things around — reach out directly on LinkedIn or via his site.