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 Nazaral — Peer advisor referenced during a pivotal deal moment

LinkedIn — Kish Patel

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How the Deal Was Done hosted by Matthew Klingner.

New episodes every week.

Bas Pleune is the newly appointed CRO of Garde, and former enterprise seller at ContentSquare where he spent four years transforming a broken, problem-riddled account into one of the company's most strategic partnerships. He didn't win this account — he inherited it.

The technology hadn't delivered, the champion was frustrated, and the contract was at risk. What followed was a masterclass in patience, relationship architecture, and systematic enterprise selling.

Key Takeaways

The org chart as a trust weapon. Bas mapped every stakeholder, reporting line, and informal power dynamic across four years. He used it to brief new champions, earn internal credibility, and open doors into parts of the organization he hadn't reached yet.

Align your internal team to their own KPIs. SDRs are measured on number of opportunities — so give them ten smaller ones inside one account. CSMs want multiple active users — so expand the footprint. Pre-sales wants to close — so bring them in strategically. Make it easy for everyone to win by helping you.

Use the buying process as a competitive weapon. When champions mentioned evaluating competitors, Bas asked one question: are they registered vendors? He knew they weren't. Then he painted the picture of exactly what that procurement process would cost them personally — and offered to save them the trouble.

The tag-along close. Found a champion with enough priority and political capital to drive a deal through procurement? Use their momentum to pull through the lower-priority opportunities that couldn't close alone. Bundle them in and move together.

Cloud marketplace as a deal accelerator. Routing deals through AWS, Microsoft, or Google marketplaces lets customers draw down on pre-committed cloud spend — unlocking higher discount brackets and aligning IT, procurement, and the hyperscaler rep all at once.

Science over art. The best sales leaders — including some who are engineers by training — treat selling as a machine. Curiosity, business acumen, and financial literacy are the inputs. Everything else follows.

Resources & People Mentioned

• ContentSquare — Digital experience analytics platform: contentsquare.com
• Guardey — Bas's current company as CRO: garde.com
• Nate Nasralla — Fluint CEO, referenced on emotional storytelling in deals: fluint.io
• John McMahon — Referenced on the science of enterprise sales, author of The Qualified Sales Leader
• Brandt Williams — Guest recommendation, former colleague, seller turned entrepreneur
• Jamie Ritchie — Guest recommendation, top enterprise seller at ContentSquare UK
• Jamal Reimer — Enterprise sellers community, where Bas and Matthew connected

Connect

• Bas Pleune: LinkedIn