SaaStr 034: How To Master The Freemium Model, Learnings From Being The 1st Sales Hire @ Box & Dropbox & The Integration of Sales and Engineering with Front's New Head of Sales, Cailen D'sa

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? If you would like to find out more about the show and the guests presented you can follow us on Twitter here: Jason Lemkin Harry Stebbings Saastr Cailen D’sa This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com