Marketing Operators — EP 80

“Chat GPT Shopping, Striking a Balance with SMS & How We’d Build a Marketing Team from Day One”
Hosts: Connor Rolain, Connor MacDonald, Cody Plofker
Date: October 7, 2025

Episode Overview

In this episode, Connor Rolain and Cody Plofker dive deep into three primary topics:

1. ChatGPT Shopping & the Shopify Integration: What does the rise of shopping via large language models mean for brands, and how should operators approach generative AI as a channel in their media mix?
2. Striking a Balance with SMS: Testing, data, and the counterintuitive lessons from incrementality-driven SMS strategies—how aggressive can brands get?
3. Drafting a Day-One Marketing Team: If you were launching a brand from scratch (with zero revenue), who are your first three key marketing hires and why?

Throughout, the conversation is grounded in direct experience, operator know-how, and clear-eyed experimentation, mixed with moments of humor and friendly banter.

Key Discussion Points & Insights

1. ChatGPT & LLM Shopping: Is This the Next Great Channel for Brands?

[10:22 - 26:48]

• Shopify's ChatGPT Integration:
  Cody introduces the recent rollout—a direct Shopify-ChatGPT integration—which may shape the 2026 e-commerce landscape.
• Cautious Excitement & "Shiny Object Syndrome":
  Both hosts are wary of over-indexing on emerging channels purely because they're new. Recent history (e.g., TikTok Shop, live shopping) is filled with channels that promised more than they delivered for most brands.
  • Connor: "I’m just super wary of these things that kind of come and go... I’m a huge AI proponent, so I don’t think it’s going to come and go. I just don’t know if it’s worth hiring an agency for it right now." [11:29]
  • Cody: "Being almost anti-new-channel is a discipline you need as a marketing operator in leadership." [12:41]
• Visibility & Optimization Challenges:
  It's still a black box. Right now, ChatGPT doesn’t offer the analytics (like Search Console or Google Trends) operators are used to—making optimization tricky.
  • Cody: "You have no visibility. You can't tell where things are trending, where you're ranking. It's hard to optimize against. Frankly, it's just kind of a black box." [18:01]
• Who Can Win on ChatGPT Shopping?
  • Larger, established brands (with "a ten year head start of seeding the internet") have an early advantage—if your product dominates search and social chatter, you'll be referenced more.
  • For smaller, niche offerings: there are growth-hacking opportunities in targeting long-tail product and benefit queries, and even "astroturfing" Reddit or manipulating cited sources.
    • Cody: "If you look at what these LLMs are referencing to generate answers, manipulating the articles that are influential in those answers is...really effective." [21:35]
• Is the Website Going Away?
  Both think digital storefronts aren’t going anywhere soon, even as transactional context shifts toward chat, mobile, and integrations: "[Shopify] will become more of a logistics and operations company...but there’s still value in having a digital storefront.” —Connor [23:47]

2. Striking a Balance with SMS: Frequency, Data, & Brand Approach

[27:02 - 38:37]

• How Many SMS Messages Should You Send?
  The wild story of a brand sending 23 messages in 30 days: is this aggressive or smart?
• Testing Wins Over Intuition:
  The data says: you can generally send more than you'd expect before hitting negative returns on unsubscribe rates or engagement.
  • Connor: "Every time we've tested, sending more performs better than sending less." [22:22]
  • Cody: "We had three segments—one message, three messages, six messages...as you send more messages the value of each one decreases, but it’s still very positive ROI." [31:26]
• Timing and Moment of Maximum Incrementality:
  It's often immediately post-purchase, not after the product is delivered, where follow-up messaging is most effective.
  • Cody: "Intuitively you would think…let them receive the product. But really, we continue to move that messaging up, and they’re just more likely to purchase." [30:30]
• Segmentation & Campaign Frequency:
  The optimal strategy may involve a “highly engaged period” right after first purchase, then pulling back for later high-conversion moments (like BFCM).
• Unsubscribes Are Sometimes Worth the Incremental Revenue:
  Strong performers justify higher frequency even if unsubscribes tick up slightly. Measurement tools like Subscriber LTV (SLTV) from Postscript help balance ROI.
  • Cody: "If you can generate an additional $0.41 per message, it’s almost always better than worrying about the 2% of people who are going to unsubscribe." [34:26]
• Order Notifications: Email vs SMS?
  Non-transactional notifications (order out for delivery, etc.) are often better suited for email to save SMS costs unless there’s a clear experience benefit.
  • "We just email…there's a good cost savings that we get. But, you know, Groons is probably choosing that—they think it’s a customer experience improvement.” —Connor [37:31]

3. Pro Tips: Post-Purchase Offers and Upsells

[38:37 - 44:43]

• Dynamic & Personalized Offers:
  Cody explains Ridge’s approach—targeting specific product upsells (e.g. power banks to travel shoppers) in the post-purchase window and experimenting with either open shopping discounts or targeted one-click upsells.
  • “For a travel customer we’ve seen a lot of success upselling power banks afterwards. Like those products are just very complementary…” —Cody [39:29]
• "Double Dash" Post-Purchase Trick:
  Some brands are delaying fulfillment up to 8 hours post-purchase to allow a time window for email/SMS one-click upsells—emulating DoorDash’s “add another item” behavior.
  • "They wouldn't send the order to fulfillment for eight hours…and then they had an entire little mousetrap built out trying to get someone to add in a very short amount of time." —Cody [41:57]
• Testing Shipping Offers as Upsells:
  Discounting shipping (e.g. priority shipping) is seen as more palatable than product discounting; personalization and urgency can drive additional cart value.

4. Personalization for Podcast/Influencer Traffic

[46:59 - 51:34]

• URL-Based Personalization:
  For podcast/creator sponsorships, Ridge has used messaging banners or full “VIP pages” (e.g. /mkbhd) to personalize the experience and reinforce offers—these convert notably better, but can be a maintenance headache at scale.
  • "If you could send them to a personalized page, it was beneficial. It just became a question mark of how beneficial was it over time." —Cody [48:56]
• Templatization & Dynamic Updates:
  The best solution balances personalization and back-end manageability,
  • “What I'd love to do in the future is build those pages more dynamically... so they’d all have the updated Father's Day messaging.” —Cody [49:48]

5. Attribution in Podcast Advertising

[51:53 - 58:11]

• Promo Codes Under-count, Vanity URLs are Better — But Both Have Issues:
  The team agrees most conversion tracking methods under-attribute podcast/creator sales if relying solely on codes. Link clicks and post-purchase surveys provide a better, multi-signal view.
  • Connor: "If the vanity URL conversions are true, if we were just looking at discount code usage, it's undercutting it by 90%." [53:50]
  • Cody: “I hate discount code as an attribution source…I think a lot of people never use codes.” [54:09]
• Be Cautious with Survey Extrapolation:
  Over-attribution is possible if you over-index on self-reported answers.
  • “The call to action is to fill out the post purchase survey. I think those people are doing it at such a higher rate than some random person... you end up over-attributing.” —Cody [55:07]
• Podcast Advertising Matures Over Time:
  Most shows will fall into a predictable "80/20" winner distribution. Results improve as you identify and double down on the best partners.
  • "20% of the creators drove 80% of the revenue... we've chosen winners that perform relatively reliably." —Cody [56:59]

6. Fantasy Draft: Building the Day-One Marketing Team

[60:09 - 69:16]

• Connor's Picks:
  1. Director of Growth (full-stack: buying, Lander optimization, retention, some creative acumen),
  2. Director/Manager of Influencer (for creator-led growth, partnerships, and supplying accounts with content),
  3. Designer/Editor (statics, web, and creative build).
  • “Director of Growth, who’s really leading creative... and then... influencer for seeding and paid distribution... and a designer, who does web, landing page, static design.” —Connor [63:22]
• Cody's Picks:
  1. Performance Creative Strategist (mainly for great content, not just media buying),
  2. Designer/Editor,
  3. Email/SMS Marketing (believing retention is more important, and that media buying is nearly commoditized)
  • “If I was starting a brand today, you have to build your site at some point... but I’d try to create great content.” —Cody [67:24]
  • "I just want fantastic content. So I'd try to solve that with, with number one..." —Cody [65:06]
• Key Shared Theme:
  In today’s landscape, content and creative matter more than spending on buying media; a ‘generalist’ mentality wins at the very earliest stages.

Notable Quotes & Moments

• On Platform Hype Cycles & AI:
  “As marketing operators, we have to be extremely disciplined in where we’re spending time... It’s easy to chase the shiny new thing.” —Cody (12:41)
• On SMS Frequency:
  “You can send more than you think without people off... We used to think you shouldn’t send an email right away because the product isn’t delivered, but actually people are most likely to buy right away.” —Connor (22:22)
• On Personalization & Influencer Traffic:
  “If you could send them to a personalized page, it was beneficial. It just became a question mark of how beneficial was it over time because all those pages just become outdated.” —Cody (48:56)
• On Attribution Challenges:
  “I hate discount code as a like attribution source... I think a lot of people never use codes.” —Cody (54:09)
• On Early-Stage Marketing Roles:
  "Performance creative strategist is who I’d hire first—there’s so little value in tactical media buying compared to just having really great content these days." —Cody (65:06)

Timestamps for Major Segments

• [10:22] ChatGPT Shopping & Shopify Integration Overview
• [15:13] Should Smaller Brands Prioritize LLM/AI Shopping?
• [18:01] The Visibility Problem: SEO & Optimization Challenges with LLMs
• [27:02] SMS Strategy: Finding the Right Frequency & Balance
• [31:26] ROI Analysis on Welcome Series SMS: Diminishing Returns & Incrementality
• [38:37] Post-Purchase Offer Tactics: Dynamic & Personalized Approaches
• [46:59] Personalization for Podcast/Influencer Traffic
• [51:53] Podcast Attribution: Codes, URLs, and Surveys
• [60:09] The First Three Hires: Marketing Team Draft

Final Thoughts

This episode is a master class in real-world experimentation and deliberate marketing operations. The hosts’ skepticism of hype, coupled with a relentless focus on testing and incrementality, makes for practical, actionable conversations. If you’re grappling with AI’s role in e-commerce, SMS channel management, or structuring your first growth hires, this is essential listening.

For Further Engagement

• Let the hosts know your ideal day-one team: Tweet @marketingoperators or comment on YouTube.
• Feedback, debate, or questions? Slide into their DMs or join the discussion.