How to Win Deals That Take a Year to Close | Zac Basile (Account Director, Polly)

In this episode, I sit down with Zac Basile, Strategic Account Director at Polly, to talk about what it’s actually like to sell enterprise mortgage tech when there’s no playbook, deals take six to twelve months, and buying committees can range from a handful of stakeholders to dozens of people across the organization. Zac shares how he went from Polly’s founding AE to a sales leadership role, what it took to help build the company’s sales process from scratch, and how constant iteration shaped the way Polly sells into some of the largest lenders in the country.We also get into how long, complex deals really move forward, from early discovery and deal mapping to validating value across stakeholders and navigating late-stage redlines, negotiation, and procurement. Zac explains why time is the biggest killer of enterprise deals, why indecision is often just a slower version of no, and how he uses urgency, access, and expectation-setting to keep opportunities from stalling out. He also shares how his approach changed once the mortgage market turned, why he leaned more heavily into top-down selling during tighter market conditions, and what he now looks for when coaching AEs through stuck deals, including multi-threading, influence mapping, and figuring out who actually has decision power inside an account.TOPICS WE COVERWhat it was like being Polly’s founding AE and helping build a sales process without an established playbookHow Zac used constant iteration and customer feedback to shape the sales motion over timeWhy resilience and adaptability matter when products, messaging, and objections keep changingWhat the first 30 days of a six-to-twelve-month enterprise deal typically look likeHow Polly handles discovery, deal architecture, validation, demos, negotiation, and closingHow many stakeholders can get involved in large mortgage tech deals and why that complicates the processWhy time and indecision kill more deals than pricing or contract negotiationsHow Zac uses expectation-setting and urgency to prevent deals from quietly stalling outWhy giving prospects an easy out can be more effective than chasing dead opportunitiesABOUT THE GUESTZac Basile is the Strategic Account Director at Polly, where he focuses on strategic mortgage lender accounts and also helps lead and coach Account Executives across the organization. He was Polly’s founding AE and has spent the past five years helping build the company’s enterprise sales motion, manage complex deals, and shape go-to-market strategy in a highly relationship-driven market.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Polly: https://polly.io/