Jesse Woodbury shares his journey of converting a small proof of concept into a seven-figure deal with a B2C Home Services Company. A deal so impactful it raised the buying company’s share price. This deal is a perfect example of the power of internal champions and genuine customer relationships. Background on Jesse and the deal: Jesse Woodbury is a seasoned sales professional and Sales Players podcast host The lead came inbound from a UX manager who was reaching out to several vendors Deal Challenges: Initial lack of a clear pain point or urgency from the client's side, making it difficult to push for a substantial commitment. Distinguishing their company from the many other vendors in consideration Navigating the complexities of negotiating an unlimited usage pricing model which Jesse’s company did not regularly offer Key Learnings: The importance of building genuine relationships and having an internal champion within the client's organization can significantly influence the deal's outcome. Creative deal structuring and flexibility in pricing can open doors to larger opportunities and partnerships. Persistence and the ability to adapt sales strategies to meet client needs and internal changes can lead to groundbreaking deals. Timestamps: 0:02:24 - Jesse shares his encounter with Tim Ferriss, showcasing his admiration and the unexpected meeting that influenced him. 0:03:43 - Jesse mentions how Dustin Brown, a mentor and friend, has influenced his approach to enterprise selling. 0:08:45 - The background of the deal Jesse is discussing begins, detailing the initial contact with the UX manager from a large B2C Home Services Company. 0:15:39 - Discussion on the transition of the deal from a small proof of concept to a major project with executive involvement, including strategic outreach and negotiation phases. 0:27:21 - Jesse reflects on the impact of the deal, not just on his career but also on the client's business, highlighting the mutual benefits and the importance of relationship-building in sales. 0:29:35 - Closing remarks from Jesse and Speaker C, with an invitation for listeners to connect and explore further content. LinkedIn: https://www.linkedin.com/in/jessewoodbury/ ‘Sales Players’ podcast: https://open.spotify.com/show/1n4giaqOn4KvM9dk8b6Nm2 Jesse referred by Dustin Brown - link to Dustin Brown episode: https://www.dealstoriespodcast.com/episodes/ep-25-expanding-a-fortune-50-a Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/