Lauren Weinberg is a proud boy mom, a loving dog mom—and currently—the Chief Marketing and Communications Officer at Square, driving the brand’s global marketing and communications strategy. She started her career by measuring media metrics, then entered B2B media and eventually moved over to the consumer side of marketing strategy. Lauren spent some time running her own consulting business, then landed at Square, where she has been for the past six years. Previously, she held leadership roles at Yahoo!, MTV, and AOL. Lauren sees marketing at Square as the growth engine, and her team is responsible for the brand, the perceptions, and acquiring new customers.

In this episode, Lauren and I discuss Square’s business model, how it has dimensionalized and expanded over the years, the impact of data on Square’s marketing efforts, and the incrementalism and principled risks that marketing organizations need to take to be competitive. Square started in 2009 with the purpose of enabling any individual or business to participate and thrive in the economy with the little white card reader. Now, 14 years later, they have a full ecosystem of software and hardware that allows companies of all sizes to run their entire operation through Square. With such a diverse audience, Square thrives on implementing an audience-first marketing perspective. By focusing on key audiences and tailoring messaging for each, Square can drive discoverability and cultivate relationships with a variety of different demographics and businesses in all sectors and scales. Square is very data-driven and informed, so everything they do and plans for is tied back to the overall strategy, metrics of success, and business results. Their category is competitive, so they have to be responsive and adapt quickly while also being smart with their risk-taking. Lauren tells us taking small incremental risks gives them space to break through and try new things. Thankfully, experimenting and learning from failures is in Square’s DNA, which serves them well in being innovative. Lauren’s marketing teams measure their success on how much revenue they bring in from the new customers they acquire. She tells us it’s a blessing and a curse to be in the spotlight with their contributions so directly linked to the business’s success, but she thrives on the challenge.

In this episode, you’ll learn:

  • The benefits and challenges of implementing “audience first” marketing
  • How incrementalism, principled risks, and a culture of learning drive innovation at Square
  • Laurens take on marketing cuts in light of an oncoming recession

Key Highlights:

  • [01:30] A cross-country pandemic move
  • [05:00] Where Lauren got her start and how she ended up at Square
  • [09:00] What is Square today
  • [10:30] How does Lauren think about marketing role in driving growth
  • [12:00] What has Lauren learned at Square over the past six years?
  • [13:20] How is Lauren using data to inform her marketing efforts?
  • [15:40] Data in understanding long-term investments
  • [16:48] Marketing mix modleing
  • [19:05] Educating a variety of audiences
  • [21:40] Audience first marketing
  • [24:30] Marketing cuts in light of an oncoming recession
  • [27:50] Benefits of constant communication and transparent decision making
  • [30:00] The impact of her first job and being a boy mom
  • [32:30] Advocate for yourself and trust your intuition
  • [34:30] Generative Ai and unlocking TikTok
  • [36:00] Trends and subcultures to watch
  • [38:45] Returning to a beginners mindset

Resources Mentioned:

Follow the podcast:

Connect with the Guest:

Connect with Marketing Today and Alan Hart:

Post-Production Credits:


Alan B. Hart is the creator and host of “Marketing Today with Alan Hart,” a weekly podcast where he interviews leading global marketing professionals and business leaders. Alan advises leading executives and marketing teams on brand, customer experience, innovation, and growth opportunities. He has consulted with Fortune 100 companies but is an entrepreneur at his core, having founded or served as an executive for nine companies.