Welcome to Episode 34! I am delighted to welcome the new Head of Sales at Front, 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 at 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 head over to Front’s blog where you can find Mathilde Collin’s written interview with Cailen.Cailen_DSa

In this episode with Cailen you will learn:
How did Cailen come to be the first Sales hire at 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 its role in sales, to what extent does Cailen still believe sales to be an art and not a science?

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Jason Lemkin
Harry Stebbings
Cailen D’Sa

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