How the Deal Was Done | Sarah Thomas, Strategic AE at Verkada

Sarah Thomas closed the biggest deal in Verkada history. 1,000 retail franchise locations, a skeptical new champion, a botched proof of concept, and a three-party sell across customer, integrator, and Verkada internally.

The deal nearly died over a scope miscommunication that put her integrity on the line. She revived it by owning the mistake, renegotiating the structure, and rebuilding trust at every layer.

In this episode:

• How to run parallel prospecting threads across a channel deal
• What to do when your pilot surfaces a broken promise
• How to beat a cheaper competitor on total cost of ownership
• Why selling year four matters more than winning year one
• How to structure staggered licensing around implementation reality

Key Quotes

"The customer said we had communicated one thing in the sales process — and during the POC it looked different. My integrity was challenged. But we owned our part of it."

"How do they trust us year two, year three, year four? Not just buying equipment — truly partnering."

"Can you even spend this money? It's uncomfortable asking, but maybe not as soon as I should."

Resources MentionedFanatical Prospecting — Jeb BlountGong — deal intelligence and call reviewGemini — prospecting and account research

Connect with SarahLinkedIn: Sarah Thomas, Strategic Account Executive, Verkada

How the Deal Was Done | Host: Matthew KlingnerFor senior AEs, founders, and GTM leaders who want to close bigger, more complex deals.

How the Deal Was Done
Episode: Philipp Klein, From Legal Threats to a $1M Win
Guest: Philipp Klein, Enterprise Account Director Companies: Blinkist | CoachHub Industry: Learning & Development / HR Tech
Episode Summary
Philip Klein joined CoachHub as one of its first five employees in 2019. In this episode, he walks through one of the most dramatic enterprise deals in the company's history — a nearly seven-figure coaching platform sale to Booking.com that spanned two years, survived a legal threat, and navigated a global pandemic.
Key Moments in the Deal
1. The Lead Came from an SDR Philipp credits the shared-room culture of celebrating every small win as the foundation that made the deal possible. That buzz and collective energy often makes up for what early-stage teams lack in formal training.

2. Qualifying for Transformation, Not Just Interest CoachHub's calendar was full of the wrong meetings — coaching enthusiasts who wanted to coach 10–15 people. Booking.com's team was different: they asked how CoachHub could scale and weren't scared of big numbers.

3. Reframing the Demo Request Rather than handing over access to an immature product, Philipp asked prospects to articulate what they actually needed to evaluate. That unlocked 4–5 additional stakeholder meetings that competitors — who just sent the login — likely never got.

4. The Legal Crisis Days after signing the pilot, Booking.com went dark, then sent a formal email threatening legal action over a data privacy dispute. Philip's response: mapped stakeholders on LinkedIn, escalated to senior management, and brought in the CEO and Chief Legal Officer to a recovery meeting. The CLO's command of data privacy law reestablished credibility and broke the impasse.

5. COVID as an Unexpected Catalyst When the pandemic froze Booking.com's business, CoachHub kept dialing. They proposed a small global pilot — 15 senior decision-makers at HQ — to stay relevant and transition from vendor to strategic partner. When budgets unfroze, they were first in line.

6. Closing the Big Deal By late 2020, the close was — in Philip's words — the easier part. Financial incentives pulled the deal from December to November, and implementation meetings were already in stakeholders' calendars before the signature. The deal closed itself through the gate they'd built.
Quotable Moments

"The signature is basically just a gate the customer has to go through. Otherwise they cannot get to the next room."
"You don't build confidence from successes. You build it from a mixture of successes and failures."

"The difficult groundwork is what we did before. The big close was actually the easier part."
Resources & Links
Connect with Philipp

• LinkedIn: https://www.linkedin.com/in/philippklein/
• Case study video: Search "CoachHub Booking.com" to see the video he negotiated into the contract

How the Deal Was Done drops weekly. Subscribe wherever you listen to podcasts

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