Podcast Summary: Behind the Numbers: an EMARKETER Podcast
Episode: Does Every Retailer Need a Chief Entertainment Officer (Like GAP)? | Reimagining Retail
Date: March 4, 2026
Host: Susie Dava Kenyon
Guests: Blake Drosch (Senior Analyst), Sky Canavas (Principal Analyst)

Overview

In this episode, host Susie Dava Kenyon and her guests explore Gap's bold move to appoint a Chief Entertainment Officer (CEO) and the broader implications for the retail industry. They discuss the rising trend of retailers leaning into media and entertainment, the blurred lines between content and commerce, and whether Gap's approach is a fleeting headline or a genuine evolution. The conversation probes the role and purpose of such a position, the challenges of integrating entertainment with sales, and if this tactic is scalable for other retailers.

Key Discussion Points & Insights

1. The Rise of “Fashiontainment” and Entertainment in Retail

• Gap’s Strategy: Gap is establishing a Los Angeles office and building partnerships across music, film, sports, and gaming, aiming to create “fandom” and achieve long-term relevance. (00:40)
• Industry Trend: This move echoes predictions from EMARKETER's 2025 retail trends about retailers taking a bigger stake in media and entertainment.

2. Branded Content: Examples and Impact

• Memorable Branded Films: Discussion of how brand films like “Barbie” and “The Founder” (about McDonald's) have influenced perceptions and purchasing behaviors.
  • Sky: "I definitely watched the Barbie movie with my daughter and we both really enjoyed it...drove a lot of affinity for the brand." (01:46)
  • Blake: “I would be remiss as well if I didn’t mention also the 2016 movie, The Founder with Michael Keaton about the founder of McDonald's...it definitely made me hungry for McDonald's.” (02:25)

3. The Role and Ambiguity of the Chief Entertainment Officer

• What Makes It Distinct?
  • Blake: “I think the examples that we just gave...are very different from what the Gap is doing here, which is trying to...facilitate partnerships across the entertainment space...I’m just wondering how exactly this is going to look different.” (03:47)
  • Sky: “This appointment really puts the spotlight on the fact that Gap wants to put, like, Capital E Entertainment at the center of its brand...the role of the Chief Entertainment Officer will be to think more broadly and link those viral moments to create a cohesive brand narrative…” (04:41)
• Org Structure: The CEO of Entertainment is positioned “above” CMOs for individual brands, focusing more on IP and high-level partnerships than on direct campaigns. (08:02)

4. Headline Move or Structural Shift?

• Title for Buzz vs. Real Shift:
  • Blake: “Is this just another way of trying to think about more ways to make money?...It’s almost like they’re running out of, you know, new C suite names that are essentially just maybe a different flavor of CMO.” (09:22)
  • Sky: “The title was maybe partly designed to grab headlines...but I think longer term, it signals an emphasis on quality content, that it’s not just going to be advertising or performance marketing.” (10:34)
• Industry Examples: Other brands like Fanatics and LVMH have launched production studios; Dick's Sporting Goods has expanded its creator program.

5. Measuring Success of the Chief Entertainment Officer

• Challenges in Measurement:
  • Blake: “There's probably gonna have to be leniency because it isn’t sort of a new role, it’s an ambiguous role...this move clearly sits within the realm of brand building, which is always hard to measure, even if fully operating at scale.” (13:46)
  • Possible metrics: Media impact value, brand awareness, brand affinity, new-to-brand customers, and long-term sales impact (14:55).

6. Risk and Reward—Evolution vs. Distraction

• Core Question: Is this a bold transformation or a distraction from retail fundamentals?
  • Blake: “I would say it’s probably somewhere in between...I think it’s smart...but they have a long way to go before they can restore the cultural relevance they once had.” (17:48)
  • Sky: “It is a bold transformation move that is becoming more fundamental to brands in retail just because the environment is so much more competitive than it was 20, 30 years ago...” (19:16)
• Fundamentals Still Matter: Both guests stress that merchandise quality, retail basics, and seamless ecommerce remain crucial.

7. Scalability for Other Retailers

• Not One-Size-Fits-All:
  • Sky: “I think every brand should have a brand building content strategy that has a strong entertainment or cultural component...Entertainment nowadays takes so many forms—it can be both entertaining and informative.” (20:19)

Notable Quotes & Memorable Moments

• Sky Canavas (01:46):
  “I definitely watched the Barbie movie with my daughter and we both really enjoyed it and I think it was a great piece of brand content that told the story and really drove a lot of affinity for the brand and purchases. Possibly, possibly.”

• Blake Drosch (02:25):
  “I would be remiss as well if I didn’t mention also the 2016 movie, The Founder with Michael Keaton about the founder of McDonald's, which I think is also a great movie about the birth of an iconic brand and definitely made me hungry for McDonald's.”

• Sky Canavas (04:41):
  “I think the role of the Chief Entertainment Officer will be to think more broadly and how to kind of link those viral moments to create a cohesive brand narrative or strategy...that can capitalize on viral moments but isn’t solely dependent on them.”

• Blake Drosch (09:22):
  "It’s almost like they’re running out of, you know, new C suite names that are essentially just maybe a different flavor of CMO..."

• Sky Canavas (10:34):
  "I think longer term, it signals an emphasis on the quality content, that it’s not just going to be advertising campaigns or performance marketing...what sits at the top will be higher quality entertainment content that’s linked to culture..."

• Blake Drosch (13:46):
  “There's probably gonna have to be leniency because it isn’t sort of a new role, it’s an ambiguous role...I think this is clearly a role that sits within the realm of brand building, which is always hard to measure...”

• Sky Canavas (19:16):
  “It is a bold transformation move that is becoming more fundamental to brands in retail just because the environment is so much more competitive than it was 20, 30 years ago when Gap was at its heyday and had a central role in our culture.”

Timestamps for Important Segments

• 00:40 – Gap’s entertainment push: The fashiontainment strategy and rationale.
• 01:46 – Discussing the power of branded content: Barbie, McDonald’s “The Founder,” Lego.
• 04:41 – What does a Chief Entertainment Officer actually do? Differentiation and organizational structure.
• 08:02 – Distinction between marketing/CMO roles and the entertainment office.
• 09:22 – Is this just another C-suite title or real change?
• 10:34 – The long-term vision: content quality as a strategic differentiator.
• 13:46 – Measuring success: What would prove out the CEO of Entertainment role.
• 17:48 – Is this a bold move or a distraction from retail fundamentals?
• 19:16 – The necessity of bold transformation in a crowded, competitive retail market.
• 20:19 – Can every retailer do this? The need for content and entertainment strategy.

Tone & Style

• Conversational, insightful, and a bit skeptical.
• Frequent use of anecdotes and humor.
• Balanced, with both enthusiasm for bold industry moves and practical caution about core retail fundamentals.

Takeaways

• Gap's creation of a Chief Entertainment Officer marks a significant, if not entirely unprecedented, shift in retail, blending brand, commerce, and entertainment into a single strategy.
• The boundaries between marketing, entertainment, and commerce are blurring—retailers must innovate to stay culturally relevant.
• The success of this strategy hinges on more than just viral moments; the basic strength of the merchandise and the organization’s ability to build long-term narratives are essential.
• The role’s effectiveness may not be immediately apparent and is hard to quantify; patience and holistic brand-building metrics will be key.
• Not all retailers need to appoint a Chief Entertainment Officer, but all need to seriously consider how entertainment—or at least compelling storytelling—fits into their brand building in the new retail landscape.