How the Deal was Done | Enterprise Sales Podcast

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 learnings he has picked up throughout his career. For salespeople, Rob offers advice and tactics that have driven his unrivaled success. For everyone, Rob shares his perspective on how to live a hard-working, happy and purpose-driven life. For Rob, that purpose drives him to continually be a builder of companies, a competitive athlete, and a proud family man and father. Chapter Markers: 0:00:00 - Intro 0:00:39 - Sales Origins 0:16:27 - Ariba Beginnings 0:23:49 - The $10 Million Dollar Phillips Deal 0:41:17 - Money & Time 1:03:53 - Advice 1:13:09 - Legacy A special thank you to Gary Griffith who helped create the opportunity for us to share Rob's inspiring story. Check out the video version of this podcast on YouTube To learn more about How the Deal was Done Podcast - you can subscribe at www.DealStoriesPodcast.com or reach out to host Andrew Kappel on LinkedIn

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 and diverse career in sales, authoring several books and hosting successful podcasts. 
 The deal involved selling a complex real-time entertainment system to a Fortune 500 media company, which required custom development and cost approximately $12 million. 
 Challenges: The company made a critical pricing error, requiring them to double the cost at the last minute. 
 The deal involved creating a product that didn't yet exist, necessitating true collaboration with the buyer. 
 Key Learnings: Building and maintaining trust is crucial, especially when unexpected challenges arise. 
 Sales success often hinges on deeply understanding the customer's needs and being adaptable in addressing them. 
 Timestamps: (02:37) Andy Paul's entry into sales (05:05) Initial connection with the big media company (08:37) Technical challenges in developing the product (12:21) Critical pricing error and how it was handled (17:18) Importance of the buyer’s experience with the seller (27:30) The value of deep understanding in sales 
 Resources:
 Follow ⁠Mitchell Kasprzyk on LinkedIn⁠ Follow ⁠Andy Paul on LinkedIn⁠Thank you to ⁠Fluint⁠ for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room.  Check out their solution here: ⁠fluint.io/dealpod Questions, comments, ideas - reach out to ⁠⁠Andrew Kappel on LinkedIn⁠

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.
Background:​Covers deal setup and the process and relationship development with the AE who won the new logo and the championChallenges:​Aligning customer's needs with Gong's product roadmap​Coordinating with internal leadership to build trust and relationships with the customerKey Learnings:​Focus on being a trusted partner to help overcome speed bumps in the deal cycleKnow the skills that you need and work backwards to develop those skills
Timestamps:(02:00) - Ian's career journey so far(03:15) - Start of the deal(05:40) - Main challenges in the deal(08:15) - Expanding the deal(10:30) - Strategies for getting better(13:50) - Connect with Ian 
Resources:Connect with Ian on LinkedInLearn more about LeaderLevThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: ⁠Andrew Kappel

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 InsideSales.com and later founding startups like Conversature and Pclub.io​The deal involved selling Pclub's skill transformation platform to a marketing automation company for $110,000, spanning multiple departments and requiring extensive multithreading.Challenges:​Procurement demanded a significant discount, initially offering a budget far below the quoted price.​Ensuring differentiation and building a strong business case to justify the higher price point against competitors.Key learnings:​The importance of undeniable defensibility, including quantified value, differentiation, and powerful champions.​The value of a multithreaded network and having a compelling event to anchor the negotiation timeline.Timestamps:01:02 – Chris's career journey split across being a seller, leader, and entrepreneur.03:41 – Founding Conversature and its challenges.06:24 – Overview of Pclub's skill transformation platform.08:37 – How the deal started with individual subscriptions leading to enterprise interest similar to PLG model11:03 – Challenges with procurement and the negotiation process.18:48 – Key strategy for successful negotiation: undeniable defensibility.
Resources:Find Chris Orlob on LinkedInThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel


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 Challenges: Long sales cycle over two+ years Various starts and stops and executive turnover Need to align with the client’s budgeting periods and fit into larger software migration a la implementation of a new CRM or ERP. Key Learnings: The importance of multi-threading and engaging with multiple stakeholders early in the sales process. Using Fluint's written business case framework to improve discovery and effectively communicate the economic impact to the client. Timestamps: (0:02:46) Deal OverviewDetails and background about Hailey's company and the end-user client (0:04:25) Challenges in the DealDiscussing the hurdles faced during the sales process. (0:05:57) Integration StrategyHow Nivvon’s software integrates with the client’s systems. (0:08:24) Champion TransitionHandling the transition of the internal champion at the client’s organization. (0:14:09) Utilizing FluentThe impact of using Fluint's business case framework on the deal’s success. Resources: LinkedIn: Hailey Ben-IzhakThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel

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 Now, Caleb also works with HubSpot partners as a Founding Account Exec at Supered. The deal involved a large multinational company, closed in two weeks, and accounted for 95% of Caleb's monthly quota. Challenges: The deal followed no traditional sales or prospecting playbooks. Internal processes and demands for multiple meetings risked slowing down the deal. Key Learnings: Recognize and give special attention to outlier deals. Build a process-driven day but remain open to the unpredictability of sales. Timestamps: 00:56 – Caleb King's background and role at Supered02:59 – Overview of the whale deal from HubSpot04:13 – Selling through the channel and the unique company involved06:07 – Internal operations and managing risk for the deal08:24 – Key learnings from the deal and the importance of process09:49 – Relationship with the rev ops agency involved12:03 – Supered's go-to-market strategy and the concept of the dark funnel Resources: Find Caleb King on LinkedIn Check out Supered Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod Questions, comments, ideas - reach out to: Andrew Kappel

Mitchell Kasprzyk, VP of Sales at Compyl, shares a pivotal deal story that led to a significant funding round for his organization. His journey from opera singer to sales leader adds a unique twist to his approach and philosophy in selling. Background: Mitchell Kasprzyk started his career as an opera singer before transitioning to sales, now serving as VP of Sales at Compyl. The deal involved a significant round of funding for Compyl, initiated through a first call with the CTO of a larger parent organization. Challenges: The CTO's initial resistance, stating he didn't want a sales pitch and wanted to see the tool directly. Overcoming the underdog status of being a lesser-known startup in a competitive cybersecurity market. Key learnings: Demonstrating transparency and empathy can build trust even with initially resistant clients. Understanding and addressing the specific business outcomes and challenges of the client is crucial. Timestamps: 0:00:02 - Introduction and welcome 0:00:26 - Mitchell's career background 0:03:44 - Initial challenge with the CTO 0:06:11 - Networking at an industry event 0:09:34 - Developing the business case 0:15:08 - Key lessons from the deal 0:21:10 - Parallels between opera and sales Resources: Follow Mitchell Kasprzyk on LinkedIn Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod Questions, comments, ideas - reach out to ⁠Andrew Kappel on LinkedIn

Samantha Price shares her career journey from journalism to sales and details a recent significant deal she closed at Persefoni. She highlights the unique challenges of selling sustainability software to Fortune 500 companies and the strategies she uses to succeed. Background: Samantha transitioned from journalism to sales and now works at Persefoni, focusing on environmental sustainability. She closed a sustainability software deal with a Fortune 500 company; utilizing the Fluint one-page business case to simplify the process by aligning both internal and external stakeholders. Challenges: Selling sustainability software to buyers unfamiliar with purchasing software. Navigating the complexities of budget approval and competitive differentiation in a niche market. Key learnings: Simplifying communication and reducing friction for buyers is crucial. Leveraging relationships and industry connections can open significant opportunities. Timestamps: (0:00:00) - Background of Samantha Price (0:05:27) - Challenges in selling sustainability software (0:07:32) - Insights on understanding buyer's needs (0:10:50) - Strategies for simplifying communication (0:13:19) - Success and replication of the deal (0:14:37) - Benefits of using Fluint to create business cases with your buyers Resources: Follow Samantha Price on LinkedIn Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution here: ⁠fluint.io/dealpod Questions, comments, ideas - reach out to ⁠Andrew Kappel on LinkedIn