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 147: Why Payback Period Is The Critical Metric, Why There Is No "No Man's Land In SaaS Pricing" & When Is A Stretch VP, A Stretch Too Far with Shan Sinha, Founder & CEO @ Highfive

Shan Sinha is the Founder & CEO @ Highfive, the startup that quite simply makes insanely simple video conferencing. They have raised over $45m in funding from some of the best in the business including a16z, Lightspeed General Catalyst and Founder Collective and then individuals including Aaron Levie, Drew Houston and Marc Benioff. Prior to Highfive, Shan was the Group Product Manager for Google Apps for Enterprise, which he joined following Google’s 2010 acquisition of his prior company, DocVerse, which later became part of Google Drive.

In Today’s Episode You Will Learn:

  • How Shan made his way from being one of the foundations of Google Drive to changing the world of video conferencing with Highfive?
  • As a successful second time founder, how has Shan’s thesis around customer success changed? When is the right time to hire your first CS personnel? What profile should those first CS hires have? How does this vary to differing profiles in the scaling journey?
  • Logos or expansion? What does Shan believe is crucial in the early days of SaaS scaling? What metric is the true determinant of whether a customer is attaining consistent value from your product?
  • Why does Shan believe that not everything has to scale from Day 1? What are the benefits of implementing a model that is unable to scale? What does this show and teach the startup? How does Shan think about capturing the perfect customer experience?
  • Why does Shan believe that payback period is the single most important metric for SaaS startups? How does Shan think about payback and margins when selling to the traditionally smaller ACV marker of SMB? What are the challenges in doing so?

60 Second SaaStr

  1. When is a stretch VP a stretch too far?
  2. What does Shan know now that he wishes had known when he started Highfive?
  3. Challenges of doing both hardware and software simultaneously?

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


Shan Sinha

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


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