How Sales Leaders Win Their Biggest Deals | Chris Essex

Chris Essex has spent over fifteen years building go to market teams inside cybersecurity companies backed by private equity, helping founders and investors grow businesses through rapid acquisitions and eventual exits. In this episode, he breaks down how the best sales leaders structure a war room, why the RFP response is never the thing you actually win on, and what separates teams that get to the negotiating table from teams that get left as fodder on price. Chris also talks candidly about his most painful losses, why training and methodology are not optional extras, and how AI is changing research without changing the fact that people still buy from people they trust. He closes with the three things he tells every new sales leader to focus on in their first year. Why a war room only matters for the top ten percent of deals, and how to run one properly The difference between winning on paper and winning the relationship How to identify the real decision maker versus the person who just signs off Why AI speeds up research but still can't replace human trust in a sale The biggest mistake sales leaders make heading into year three Three tips for any new sales leader or CRO starting fresh If you enjoyed this conversation, please like, share, and subscribe. Sam and the Shipley Podcasts team I hope you enjoy this episode! If you did, please like, subscribe and share it with someone who'd get value from it. - Sam, Tony, and the Lessons from the Win Room podcast team Connect with us here:  Sam Singh: https://uk.linkedin.com/in/samsinghofshipleywins  Tony Birch: https://www.linkedin.com/in/tony-birch-1b41742/  Website:  shipleywins.nl shipleywins.co.uk shipleywins.in Listen to Lessons from the Win Room on these platforms:  Listen on Spotify: https://open.spotify.com/show/0GBSQ63yQN7ERtu3p4pxRk Listen on Apple Podcasts: https://podcasts.apple.com/podcast/lessons-from-the-win-room/id6808622275 Listen on Amazon Podcasts: https://music.amazon.com/podcasts/4dfa996a-9813-4aa9-b87d-9adb628c2ea1 #lessonsfromthewinroom #bidmanagement #proposalmanagement #salesleadership #businessdevelopment #capturemanagement #commercialstrategy #b2bsales #executiveinterview #apmp #salesenablement #aiinsales #benelux #ukbusiness #winningmorebusiness Lessons from the Win Room is a podcast from Shipley UK, Shipley Benelux, Shipley India and Africa, bringing commercial leaders together to talk honestly about how they actually win business. It's hosted by two voices from within the Shipley partnership: Tony Birch, Chairman of Shipley UK and an APMP Fellow with over thirty years in bid and proposal management, and Sam Singh, who leads Shipley Benelux across Belgium, the Netherlands and Luxembourg. Each episode explores how commercial leaders plan and run their own "Win Room", the strategies, levers and obstructions behind consistent bid success. Conversations cover the UK's defence, aerospace, rail, construction and nuclear sectors alongside cross-sector business growth topics from across the Benelux region, including how AI is reshaping trust between buyers and sellers. The show is built for bid managers, proposal leads, L&D directors and commercial decision makers who want a practical, grounded look at what separates consistent winners from everyone else. Expect real conversation and honest reflection rather than a polished pitch.