In episode five of The Deal Desk, we sat down with Chris Redmond, Director of Customer Base for Tech Media, and Professional Services at Workday, for a conversation about preparation, leadership, forecasting, and what it takes to build a successful sales career without losing sight of what matters most. Chris shares his 11-year journey at Workday, from starting in the LIFT rotational program to becoming a solution consultant, account executive, and now a sales leader. He reflects on the lessons he learned from seeing hundreds of deal cycles up close, including why the best sellers are relentlessly prepared, how great deal teams use discovery to shape the next conversation, and why dry runs and debriefs are essential to getting better. Whether you’re an account executive, solution consultant, aspiring leader, or working parent trying to do both well, this conversation offers grounded, real-world insight on how to lead, sell, and grow with intention. 🎙️🎧 Tune in to The Deal Desk for candid conversations about sales, strategy, and leadership—straight from the Workmates doing the work. Learn more about Sales careers at Workday here: https://w.day/SalesCareersYT

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