HOW TO SELL CHANGE INTO THE ENTERPRISE - TAYLOR WILDING, XACTLY - VP OF SALES

20 Feb 2024 · 52 min
The Brutal Truth about Sales and Selling - We interview the world's best B2B Enterprise salespeople.

20 Feb 2024 · 52 min

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In this episode of the Closing the Complex Sale podcast, host Brian Burns interviews Taylor Wilding, Vice President of Sales for Xactly North America, about the unique challenges of selling enterprise‑level SaaS that forces organizations to change how they manage commissions, quota planning, and revenue forecasting. The conversation explores why selling change is harder than selling a product, how to map and engage multiple stakeholders across finance, HR, RevOps, and sales, and how to identify the economic buyer. Taylor explains the typical pain of relying on spreadsheets and the tipping point (about 50‑100 plan participants) where a dedicated solution becomes essential. He shares tactics for multi‑threaded prospecting, demonstrating ROI with customer‑specific over‑payment data, and maintaining momentum through seasonal buying cycles. The interview also delves into the personal traits that make a great rep in this space—storytelling, passion, hard work, and the ability to prepare for varied stakeholder questions—along with hiring criteria and interview questions to surface those traits. Throughout, Taylor draws parallels between his baseball career and sales, emphasizing competition, preparation, and resilience. The episode concludes with practical advice on avoiding single‑champion approaches, building consensus (“divide and concur”), and leveraging Xactly’s product suite (commission automation as a “Trojan horse” entry point) to expand within an organization.

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