Risky Business · Renters Legal Liability

Creative Digital Selling With Jordan Stupar

·42 min·4 clips

Jordan had his salesperson fake sleeping by a printer to close a deal—and it worked instantly.

Gary Miller opens by congratulating Jordan Stupar on his recent marriage before diving into his sales origin story. Stupar grew up with a father in sales, explicitly told him he did not want to follow that path, pursued music, and then after being fired from Chili's found his first full-time sales job via Craigslist: door-to-door alarm and security sales to residential homeowners. He spent eight years in that world, moving from Milwaukee to Chicago to Virginia to Dallas, where he spent three and a half years in the Texas heat working in residential neighborhoods. He describes that period as the fundamental education in sales: learning to handle the door slamming in your face, finding the opening line that gets someone to pause, reading body language at a threshold, and building enough rapport in the first 30 seconds to earn the next 90. Stupar then transitioned to inside sales in New York and eventually to enterprise-level deals, where he began developing his philosophy around Zoom selling, which he sees as a separate skill from phone or in-person sales. He argues that on video, credibility and preparation signal competence more than charm, and that pre-call research is non-negotiable. He discusses his use of creativity and humor to break through to C-suite executives, including sending unusual physical gifts or creating custom short videos that reference specific things about a prospect's public history or company. He breaks down his value-based follow-up approach: rather than emailing a prospect repeatedly to ask if they have made a decision, each follow-up delivers a relevant piece of content, a competitive insight, or a case study that advances the conversation. He also addresses the psychology of the longer enterprise sales cycle and why salespeople lose deals they should win by going quiet or becoming transactional during the evaluation phase.

As heard by us

Jordan Stupar keeps the focus on practical selling moves, from Zoom pitches and prospecting to objections and follow-up.

Risky Business stays in practical territory. Jordan Stupar talks through selling in a COVID world, with Zoom presentations, a little creativity and humor when closing C-suite executives, social media prospecting, shorter sales cycles, and value based follow-up.

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Why you'd press play

You want sharper Zoom selling and a cleaner way to move deals forward.

Read the full recommendation in PlayNext →

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