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 189: When to Go Large on Go-To-Market, How To Scale Company Culture with Your Team & Why Discounting is Evidence of Not Communicating Your USPs Successfully with Craig Walker, Founder & CEO @ Dialpad

Craig Walker is the Founder & CEO @ Dialpad, the startup that provides a business phone system for the modern workplace. To date, Craig has raised over $120m in VC funding with Dialpad from some of the best in the business including Iconiq, Andreesen Horowitz, Google Ventures, Felicis and Bill Marris’s Section 32. Prior to Dialpad, Craig was an EiR @ Google Ventures and founded and product managed Google Voice. Before that Craig founded Grand Central Communications, a personal communications startup that was acquired by Google. Finally prior to that, Craig enjoyed roles in the world of VC as General Partner @ Sterling Payot Capital and Founder & Senior Director of Yahoo Voice.

In Today’s Episode You Will Learn:

  • How Craig made his way into the world of SaaS following time as both a GP in the world of venture and then as the creator of what would become Google Voice?
  • Why does Craig think go-to-market is the most challenging element of being a CEO? How does Craig think about when is the right time to go large on go-to-market? Where does Craig believe most founders make mistakes here?
  • How does Craig look to balance aggressive scaling of team with the maintaining of early company culture? What are the foundations to doing this successfully? How does Craig approach the element of hiring external talent vs promotion from within? How does Craig think about managing the internal discontent if hiring an external candidate?  
  • How does Craig assess the effectiveness of trials in attracting large enterprises? What are the parameters that must be set for a trial, before it is agreed? What must founders learn to say no to when it comes to trials? How does Craig approach discounting? Why does Craig argue if your client asks for aggressive discounts, you have not explained your core USPs successfully?    

Craig’s 60 Second SaaStr

  1. What does Craig knows now that he wishes he had known at the beginning?
  2. When I say success in SaaS, who does Craig first think to and why?
  3. Quality or quantity of logos and why?

Read the full transcript on our blog.

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


Craig Walker

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