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 licensing
• The story behind the New York Jets’ “Jets Uncorked” wine
• The difference between licensing, sponsorships, and broader business partnerships
• How teams and venues can generate more revenue from alcohol programs
• Why compliance and licensing expertise matter
• How theFACTOR Agency connects venues, suppliers, sponsors, and concessionaires
• Creating experiences that extend beyond the stadium
• Training event staff to represent sponsors more effectively
• The importance of research and preparation in sales
• How AI can help sales professionals enter conversations better informed
• Why a strong value proposition opens the door to better opportunities
• How to stay focused when several attractive business opportunities emerge

KEY 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

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