How the Deal was Done | Deal Stories Podcast

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 m...

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...

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 pur...

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 transfor...

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...

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 tim...

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...

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 mastercl...

Rachit Kataria | The Only Deals Left Are the Human Ones Rachit Kataria is co-founder and CEO of Centralize, backed by Y Combinator and Salesforce Ventures. He's a product engineer by trade who built a GTM motion from zero that's now landing enterprise customers like Intercom, Brex, Highspot, LangChain, and Cresta. This episode covers the future of strategic selling in an AI world, how Rach...

Jamal Reimer is one of the most recognized voices in enterprise selling. While at Oracle, he closed three separate $50M+ transactions with major international firms - and has since built a global community, coaching practice, and an AI platform around helping senior sellers engineer deals at that scale.  He popularized the term "mega deal" long before it became a LinkedIn buzzword, and h...

Sam Quirke used sales to build his dream life (and house) in the French Alps. Then proved record-breaking success depends on dedication to client value and commitment, not location. What started as a narrow proof-of-concept with a major European media company expanded into a career-defining transaction.  Over 18 months, Sam navigated 40+ stakeholders, a 500-question RFP, and converted skeptical fi...

Danny Higdon, Founding GTM at CoverBase, shares how he closed a transformational deal that tripled his company's revenue. A Fortune 100 healthcare contract that changed the trajectory of both the business and his career.  This isn't your typical quota-crushing story; it's a masterclass in enterprise sales execution, strategic patience, and leveraging limited resources at an early-stage...

As 2024 comes to a close, and sights set on 2025, Andrew discusses major life updates including his introduction to fatherhood, his growing and evolving consulting business, and the conclusion of How the Deal was Done Podcast plus what is on the horizon. Interested in developing business cases WITH your champions? Checkout Fluint to do just that. Grab a free download of their top performing sales...

Another special guest host episode featuring Mitchell Kasprzyk. In this episode, Dave Brock shares his unique journey into sales, highlighting the importance of understanding customer needs and building trust. He recounts memorable deal stories, particularly focusing on a young salesperson's success through effective coaching. The conversation emphasizes the significance of continuous learning and...

In this episode of the Deal Stories podcast, Vince Beese, a seasoned sales leader with extensive background in sales, shares insights from his career, and focusing on a significant deal he closed with Yahoo. The highlight of this deal is navigating the RFP process, the challenges faced during negotiations, and the importance of alignment and honesty in enterprise sales. Closing it out: Vince empha...

Chas Puleo, Senior Sales Executive at Alkami, returns to in this follow-up episode to last week's conversation (Ep. 55) to discuss the closing of a 2-year, $5 million digital banking. He highlights the importance of aligning with the client’s business needs and the role of executive involvement in moving large deals forward. Background: Chas has been a Senior Sales Executive at Alkami for five an...

Chas Puleo, a senior sales executive at Alkami, shares his experience in closing a transformative $5 million deal in the digital banking space. This episode covers the challenges of resetting a deal after a key decision-maker was promoted and the importance of business cases in complex sales cycles. Background: Chas started his career in banking and transitioned into tech sales, currently at Alkam...

Quick episode here. Talking a bit behind the scenes of 'how' the new Leader Leverage Podcast came to be. You can find link to the YouTube of Ep 1 of Leader Leverage Podcast below. Also, you can checkout the new Substack newsletter that goes along with it. Thanks for listening and your support! Link to Leader Leverage Podcast ep 1 now available on YouTube

Starting by handing out flyers in grocery stores, Rob DeSantis worked his way to become a world-class seller, co-founder, and angel investor. Rob is a Co-Founder at Ariba (IPO & Acquired by SAP), early Board Member at LinkedIn, and currently a hands-on startup advisor/investor. Sales has been at the center of his success, and in this interview, Rob shares the most memorable deal and the learni...

Check out the Full Length Episode on YouTube where Rob shares the deal stories that standout from his illustrious career so far. Questions, comments, ideas - reach out to ⁠⁠ ⁠Andrew Kappel on LinkedIn⁠

Mitchell Kaspryzk re-joins the podcast this time as a guest host featuring a discussion with renowned sales expert Andy Paul. Andy shares insights from his extensive career and delve into a challenging deal involving the development of real-time entertainment systems for commercial airplanes, highlighting the importance of trust and understanding in sales. 
 Background: Andy Paul has had a long an...

Ian McDonald shares a large deal, where his company first landed the initial product sale, and the process of working hard to make them into a successful multi-product and platform customer . 
 Background: Ian McDonald is currently an AE manager at Gong with prior sales experience, at LinkedIn and CEB ​Ian shares a past deal including the account management tactics used to expand a customer. 
 Bac...

Episode 50. Thank you for listening this far. More to come! In this episode we welcome Chris Orlob who shares his boomerang journey from seller to startup founder to SaaS sales leader and now back to startup founder. For the deal we cover a recent $110,000 win for his current startup Pclub.io 
 Background: ​Chris identifies more as an entrepreneur than a sales leader, having started his career at...

Haley Ben-Izhak shares insights into closing a significant deal with a top home care provider in the US, highlighting the challenges and strategies involved. Background: Haley Ben-Izhak is an enterprise & large account executive for Nevvon; she has a background in advertising sales, event marketing, and is also a business owner. Nevvon is an online training platform for the home care industry...

Caleb King, a founding Account Executive at Supered, discusses an unusual yet highly successful deal from his time at HubSpot, emphasizing the importance of recognizing and handling outliers in sales processes. The deal involved a large multinational company and was closed in just two weeks. Background: Caleb King was a channel account manager at HubSpot working with agency and consulting partners...