Cover art for podcast The Official SaaStr Podcast: SaaS | Founders | Investors

The Official SaaStr Podcast: SaaS | Founders | Investors

469 EpisodesProduced by SaaStrWebsite

he 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 f… read more


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:

Educational emoji reaction


Interesting emoji reaction


Funny emoji reaction


Agree emoji reaction


Love emoji reaction


Wow emoji reaction


Listen to The Official SaaStr Podcast: SaaS | Founders | Investors


A free podcast app for iPhone and Android

  • User-created playlists and collections
  • Download episodes while on WiFi to listen without using mobile data
  • Stream podcast episodes without waiting for a download
  • Queue episodes to create a personal continuous playlist
RadioPublic on iOS and Android
Or by RSS
RSS feed

Connect with listeners

Podcasters use the RadioPublic listener relationship platform to build lasting connections with fans

Yes, let's begin connecting
Browser window

Find new listeners

  • A dedicated website for your podcast
  • Web embed players designed to convert visitors to listeners in the RadioPublic apps for iPhone and Android
Clicking mouse cursor

Understand your audience

  • Capture listener activity with affinity scores
  • Measure your promotional campaigns and integrate with Google and Facebook analytics
Graph of increasing value

Engage your fanbase

  • Deliver timely Calls To Action, including email acquistion for your mailing list
  • Share exactly the right moment in an episode via text, email, and social media
Icon of cellphone with money

Make money

  • Tip and transfer funds directly to podcastsers
  • Earn money for qualified plays in the RadioPublic apps with Paid Listens