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The Official SaaStr Podcast: SaaS | Founders | Investors

The Official SaaStr Podcast is the latest and greatest from the world of SaaStr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we center around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.
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Jun 27, 2016

I am delighted to welcome the new Head of Sales @ Front App, Cailen D’sa, to The Official SaaStr Podcast today. Cailen might just be the Head of Sales every SaaS startup founder is dreaming of having previously been the first sales hire @ Dropbox where he launched Dropbox’s first B2B product, prior to that he was a director at Box where he helped pioneer and operationalize the freemium land-and-expand sales model, which is now a core SaaS sales methodology. Now if you enjoy the episode with Cailen today and want to hear more from him then you must headover to Front’s blog where you can find Mathilde’s written interview with Cailen.

In This Episode With Cailen You Will Learn:

  • How did Cailen come to be the first Sales hire @ Dropbox? What was it about Front that enticed him?
  • What were Cailen’s biggest takeaways from his time at Dropbox and Box?
  • How does the Sales process differ when selling a freemium product like Dropbox, compared to an enterprise product like Front?
  • What does Cailen look for when hiring sales reps? What are Cailen’s sourcing strategies for new sales reps? How does Cailen incentivise the best talent to choose Front over other options?
  • With the rise of data and it’s role in sales, to what extent does Cailen still believe sales to be an art and not a science?

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