Calendly grew from an MVP product in 2013 to a company now valued at $3 billion. Early on, the company struggled to maintain a unique value proposition in a crowded market, monetize its users without harming customer satisfaction, and find the right level of customization to offer to users in different segments. Ultimately Calendly succeeded due to its freemium model, which helped spread organic word-of-mouth, as well as its personalized marketing to keep users engaged. Some of its successful marketing initiatives include webinars and educational content, discount code campaigns via Google Ads, and enabling its customers to embed Calendly in their own ads.