The Agile Brand with Greg Kihlström®: Expert Mode Marketing Technology, AI, & CX
Episode #766: Square CMO Lindsey Irvine on Connecting with Customers Through Community-Driven Storytelling
Release Date: November 12, 2025

Episode Overview

In this episode, Greg Kihlström hosts Lindsey Irvine, Chief Marketing Officer at Square, for an in-depth conversation about building brand relevance through authentic, community-driven storytelling. As digital noise grows and AI-generated content proliferates, their discussion focuses on how real local business owners can become a brand’s most impactful advocates, and how Square evolves its strategy to support its core customers – not just small businesses, but local businesses deeply embedded in their communities. Lindsey shares insights from Square’s “See You in the Neighborhood” campaign, and offers practical guidance on aligning brand and business strategies, measuring impact, evolving brand perceptions, and leading with an agile mindset.

Key Discussion Points & Insights

1. Defining Square’s Core Customer & Evolving Its Brand (03:13–04:46)

• Lindsey recounts Square’s journey from the “little white reader” at farmers markets, aimed at democratizing payments, to a global platform serving over 4 million businesses with a suite of commerce solutions.
• Key Insight: Square’s recent evolution centers on serving not just small businesses, but local businesses — those that are readily engaged and shaping their neighborhoods, from mom-and-pop shops to multi-location chains.

2. Brand Strategy: Community-Driven Storytelling vs. Tech-Forward Messaging (04:46–06:57)

• In a crowded fintech landscape, Square invests in genuine community storytelling.
  • Instead of focusing on features or celebrity endorsements, Square’s “See You in the Neighborhood” campaign elevates actual local business owners, amplifying authentic voices.
  • Lindsey on insight:
    “At the center, we’re for the local business, not just the small business ... our campaign platform, ‘See You in the Neighborhood,’ is far more than a tagline. It’s our promise to invest in local communities, supporting both our sellers and the neighborhoods around them.” (05:26)

3. Maintaining & Reasserting Brand Relevance (07:23–09:36)

• Lindsey’s definition of brand relevance:
  • Delivering on promises to customers
  • Continuous product innovation
  • Direct, human community engagement
• Strategies in play:
  • Deploying local Square representatives to walk neighborhoods and support sellers directly
  • Hosting events like the biannual “Square Release” to launch and gather feedback on innovations shaped by local business needs
  • Heroing local business owners rather than external celebrities in campaigns
• Memorable Quote:
  “Brand is the one thing you can’t fake. You can’t AI your way to real brand connection.” (16:06)

4. Scaling Authenticity & Choosing the Right Stories (10:16–13:07)

• Approach:
  • Begin with business strategy: identify cities and neighborhoods with growth opportunities
  • Select local business owners who are influential or central to those communities (notably, restaurants often create community hubs)
  • Capture unscripted, authentic stories by filming owners in their environments, allowing their genuine voices to lead
• Notable Process Tip:
  “No one wants to listen to a scripted customer talk ... we let them riff and tell their own story in their own words.” (12:28)

5. Measuring the Impact of Community-Driven Branding (15:28–19:21)

• Metrics utilized:
  • Long-term revenue and pipeline growth (brand creates engagement among the 95% not immediately in-market)
  • Increases in organic traffic (which converts better than paid)
  • Brand favorability and top-of-mind consideration (most buyers pick from their top 3 remembered brands)
• Lindsey’s framework:
  “In a world of AI-generated content … brand is your moat. Without it, you’re one of many.” (16:06)

6. Lessons from Leading Brand Evolution at Scale (19:21–22:44)

• Surprises:
  • Even large, established companies must still act like startups (“always stay building and always stay curious”)
  • Despite strong brand awareness, legacy perceptions persist (many still see Square solely as the ‘white reader’)
• To address this, Square:
  • Hosts regular “Square Release” events to showcase full product offerings
  • Provides ongoing communication (monthly updates, targeted campaigns, self-serve demos) to update and educate customers
• Quote:
  “We have such a rich product portfolio … but many don’t know about it. How do we be much more deliberate about the value we can provide?” (20:30)

7. The Future: AI, Relevance, and Real Human Connections (25:22–27:04)

• Lindsey’s prediction for the coming year:
  • Brands must learn to connect with both humans and AI agents, which increasingly intermediate customer journeys.
  • Staying authentic, fun, gritty, and community-driven will continue to set brands apart even as AI shapes the experience.
• Quote:
  “How does a brand show up for real humans, and also for the AI agents that are now, frankly, a customer we have to serve?” (25:49)

8. Agility in Leadership and Learning (27:25–28:16)

• Lindsey’s approach:
  • Connect with people at every level of the organization
  • Travel regularly to meet customers first-hand
  • Remain open to feedback and quick to recognize and learn from what isn’t working as well as what is
• Quote:
  “Part of being agile is not just plowing forward, but taking time to … be open and vulnerable so you can quickly course-correct.” (27:40)

Notable Quotes & Memorable Moments

• On brand authenticity:
  “No one wants to listen to a scripted customer talk ... say what is true to you. And as a result, you get really compelling, authentic, truly community-relevant content.”
  — Lindsey Irvine (12:28)
• On measuring brand’s ROI:
  “Brand allows you to reach the 95%, create interest, create excitement, create authentic connection ... so brand actually equals long-term pipeline growth.”
  — Lindsey Irvine (17:22)
• On shifting perception:
  “We don’t struggle from a brand awareness problem ... it’s the perception shift that we need to drive.”
  — Lindsey Irvine (22:51)
• On brand’s role in the AI era:
  “Brand is the one thing you can’t fake. You can’t AI your way to real brand connection, real human connection.”
  — Lindsey Irvine (16:06)
• On agility:
  “Part of being agile is not just plowing forward, but ... being open and vulnerable so you can quickly course-correct.”
  — Lindsey Irvine (27:40)

Timestamps for Key Segments

• 03:13 – Square’s Evolution: From Payments to Full-Service Platform
• 04:46 – Community-Driven Storytelling as Brand Strategy
• 07:23 – Defining and Evolving Brand Relevance
• 10:16 – Finding and Amplifying Real Local Voices at Scale
• 15:28 – Metrics: Measuring Brand’s Impact
• 19:21 – Leadership Lessons: Surprises and Brand Perception Challenges
• 22:44 – Overcoming Anchored Brand Perceptions
• 25:22 – The Future: Brand, AI, and Human Connection
• 27:25 – Practicing Agility as a Marketing Leader

Summary Takeaway

This episode presents a compelling case for brands to differentiate by relying on authentic, community-driven storytelling and real customer voices—particularly in a landscape increasingly dominated by impersonal AI-generated content and digital clutter. Lindsey Irvine underscores the importance of aligning brand strategy with business growth, measuring brand’s effect on long-term revenue, and remaining agile as both a leader and an organization. Square’s approach serves as a blueprint for companies aiming to deepen customer connections, adapt perceptions, and thrive in the rapidly evolving world of marketing technology and customer experience.