What does it take to transform a branded bottle, venue sponsorship, or cocktail program into a meaningful—and profitable—customer experience? In this episode of Sales Momentum, Howard Wolpoff speaks with Diane Karle, CEO and Co-Founder of theFACTOR Agency, about the strategy behind alcohol partnerships in sports, entertainment, hospitality, and live events. Diane explains how she recognized an underserved opportunity in licensed wine and helped create programs connecting major sports organizations with alcohol brands. What began with projects such as the New York Jets’ “Jets Uncorked” wine evolved into a broader business focused on licensing, sponsorship strategy, venue partnerships, staff training, and customer engagement. The conversation explores how teams, venues, suppliers, concessionaires, and alcohol brands can work together to generate revenue and create memorable experiences. Diane also shares examples involving Del Mar, the Breeders’ Cup, USA Today’s wine club, hospitality programs, and premium tasting experiences. Howard and Diane ultimately bring the discussion back to the fundamentals of successful selling: research, preparation, prioritization, creativity, and a clearly defined value proposition. IN THIS EPISODE How Diane identified an overlooked opportunity in sports and alcohol licensingThe story behind the New York Jets’ “Jets Uncorked” wineThe difference between licensing, sponsorships, and broader business partnershipsHow teams and venues can generate more revenue from alcohol programsWhy compliance and licensing expertise matterHow theFACTOR Agency connects venues, suppliers, sponsors, and concessionairesCreating experiences that extend beyond the stadiumTraining event staff to represent sponsors more effectivelyThe importance of research and preparation in salesHow AI can help sales professionals enter conversations better informedWhy a strong value proposition opens the door to better opportunitiesHow to stay focused when several attractive business opportunities emergeKEY TAKEAWAYS Find the unmonetized opportunity. Diane built her business by recognizing a category that sports organizations had not fully developed. Strong salespeople look for gaps where value exists but a clear solution has not yet been offered. Sell the complete business outcome. The opportunity is larger than placing a logo on a product. The most effective partnerships connect licensing, distribution, customer engagement, venue operations, sponsorship objectives, and revenue generation. Lead with research. Research allows sales professionals to enter conversations with informed ideas. Even when the initial idea is not exactly right, it can uncover the prospect’s actual priorities and lead to a stronger proposal. Create value for every participant. Successful partnerships need to benefit the team or venue, the brand, the supplier, the concessionaire, and ultimately the customer or fan. Extend the experience beyond the venue. Retail promotions, homegating programs, tastings, wine clubs, and other experiences help fans feel connected—even when they are not attending the event. Stay focused on the best opportunities. Creativity can generate many exciting possibilities, but sustainable growth requires prioritization. Diane emphasizes pursuing the opportunities most likely to advance the company’s immediate goals. CHAPTERS 00:00 – Sales Momentum introduction 01:03 – Introducing Diane Karle and theFACTOR Agency 01:58 – Why alcohol partnerships are an exciting sales category 02:40 – Discovering the opportunity in licensed sports wine 05:40 – The story behind Jets Uncorked 08:00 – Moving beyond licensing into broader partnerships 10:54 – How theFACTOR Agency structures its relationships 12:24 – Developing the USA Today wine club 13:45 – Compliance, licensing, and the value of category expertise 15:57 – The Del Mar and Breeders’ Cup experience 18:31 – Training venue staff and sponsor representatives 20:31 – The future of experiential partnerships 23:09 – Engaging fans outside the stadium 25:17 – Prioritization and sustainable business growth 27:22 – Using research and AI to prepare for sales conversations 29:38 – Final lessons and closing thoughts ABOUT THE GUEST Diane Karle is the CEO and Co-Founder of theFACTOR Agency. She specializes in developing strategic partnerships involving alcohol brands, sports organizations, entertainment properties, venues, hospitality companies, and media organizations. Her work encompasses licensing, sponsorship strategy, partnership development, experiential marketing, staff education, revenue generation, and the operational complexities of bringing alcohol programs to market. Connect with Diane Karle and theFACTOR Agency: https://www.thefactoragency.com/ ABOUT THE HOST Howard Wolpoff is a sales and leadership coach who helps professionals strengthen their selling skills, develop better strategies, and build lasting momentum. Learn more about Howard’s coaching and resources: www.HowardWolpoff.com CALL TO ACTION If you enjoyed this conversation, subscribe to Sales Momentum, share the episode with someone in your network, and leave a comment or review with your biggest takeaway. What overlooked opportunity could you help one of your prospects turn into new revenue? HASHTAGS #SalesMomentum #SalesStrategy #BusinessDevelopment #PartnershipMarketing #SportsMarketing #ExperientialMarketing #Sponsorship #Leadership #RevenueGrowth #SalesLeadership #Podcast We hope you found valuable insights to help you lead smarter, sell better, and build lasting relationships. If you enjoyed today’s conversation, don’t forget to subscribe, rate, and leave a review! Your feedback helps us bring more game-changing content to elevate your sales game. Stay connected with me on LinkedIn, https://www.linkedin.com/in/howardwolpoff/, and follow for more updates, tips, and exclusive content from the world of sales leadership. Click https://www.HowardWolpoffSWC.com to address sales coaching. 👉 Have a topic or guest suggestion? We’d love to hear from you — reach out and let us know how we can make the next episode even better! Keep pushing forward, keep evolving, and keep making those sales! 💥