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.

Kish Patel: Closing an Eight-Figure Deal in 27 Days

Kish Patel is a Strategic Director of Accounts with 15 years in enterprise selling, the last five in cybersecurity and confidential computing. In this episode, he unpacks how he displaced a seven-year incumbent — who was also that competitor's number one customer — and closed a multi-year, eight-figure contract in 27 days.

The key wasn't the product. It was financial intelligence, executive alignment, and a two-line proposal engineered directly to the CFO's bonus metrics.

• Sell the financial gap, not the feature. Kish spent 30 days researching the account before a single pitch — mapping EBITDA pressures, analyst questions, and hiring signals to understand what the business actually needed to achieve.
• Use the DEF 14A. Pull executive comp structures from public SEC filings and build your proposal around the two metrics that drive their bonuses. The CFO opened the DocuSign and signed in 30 seconds.
• Orchestrate from the outside in. Kish connected his Morgan Stanley team to the prospect's banking team to create legitimate pressure before ever getting in front of executives. The intro came with weight.
• AI is the trailer, not the movie. Use AI tools to accelerate research, but listen to the earnings calls yourself. You'll hear what the execs are proud of, what they're dodging, and what the analysts keep hammering — none of which shows up in a summary.
• Solve bigger problems, close bigger deals. If you're closing six-figure deals, you're solving seven-figure problems. Find the eight-figure problem and your deal sizes follow.

Books

• The JOLT Effect — Matt Dixon & Ted McKinnon
• Brutal Truth About Sales — Brian Burns

Tools

• Whyzer - Incredible deep research platform, geared toward financial fluency

• NotebookLM — Google's AI research tool; used to synthesize job postings into tech stack diagrams and generate audio summaries of analyst reports
• Gemini Deep Research — Used for comprehensive account research before uploading to NotebookLM
• SEC EDGAR — Search DEF 14A proxy statements and 10-K filings for any public company

People & Podcasts Referenced:

• Brian Burns — Brutal Truth About Sales Podcast (treasure map vs. treasure hunt framework)
• Nate Nasralla — Peer advisor referenced during a pivotal deal moment Fluint.io

LinkedIn — Kish Patel

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How the Deal Was Done hosted by Matthew Klingner.

New episodes every week.