With over 1.4 billion active users and million of companies entrusting it to handle their email, Gmail has a unique vantage point on how phishing groups operate. In this talk we look into Gmail telemetry to illuminate the differences between phishing groups in terms of tactics and targets. Then, leveraging insights from the cognitive and neuro-science fields on user's susceptibility and decision-making, we discuss why different types of users fall for phishing and how those insights can be used to improve phishing protections.