The International Expansion Podcast with Ramsey Pryor

Episode 3 - Ana Sofia Guzman - Co-founder of International Mastermind, fmr International Strategy and Operations at Squarespace

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In this episode, Ana Guzman shares her journey starting from El Salvador, moving to the US for university, driving Squarespace's early international expansion team, and then founding International Mastermind and a bilingual education company. She goes deep into the cross-functional effort and pre-work that her team at Squarespace undertook to properly localize their product and message for the German market, and shares lots of valuable learnings and hindsight from this experience. See below for the topics we covered during this conversation.


  • Ana's journey from El Salvador to the US and into international expansion as a career
  • How international expansion started at Squarespace, and the foundational pre-work that went in before expansion began
  • Signals and data used to help prioritize markets
  • Entering Germany - why this market was chosen first at Squarespace
  • Localization - what was required beyond translation and currency to succeed in the German market
  • The cross functional teams needed to make this happen - which departments were involved, and how to lobby for constrained resources
  • Getting buy-in and executive support behind the international initiative
  • The process and work that went into building a brand in a new market
  • The resources that helped inform Squarespace's expansion strategy
  • The importance and benefits of spending time on the ground before entry
  • What it means to be market-ready versus what it means to launch the business in a new market
  • KPIs used to measure success post-launch
  • Setting expectations and benchmarks, and communicating progress internally
  • Key learnings, and applying the lessons learned in the first market to countries that came later on
  • Keying into cultural nuances - why this matters, and an example of what resonates with German consumers vs. American consumers.
  • Product requirements and effort needed to set up a localization layer within the product.
  • International Mastermind - what this group is, and the vision that led Ana and her co-founders to start this group
  • Helpful resources that Ana reads regularly - Ben Thomspon, and Nataly Kelly's Born to be Global blog
  • Ana's advice for people who want to pursue International Expansion as a role
    • ...more
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    The International Expansion Podcast with Ramsey PryorBy Ramsey Pryor
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