Oliver Jay, former CRO at Asana and executive at Dropbox, joins Tom Tunguz of Theory Ventures to discuss the PLG trap and how to avoid it. Three primary takeaways from this discussion: 1) If you're a startup leader, revenue is fuel, particularly in this environment. 2) As you think about going from product-led to sales-led motion, it's not just about security features, it's about building the enterprise value story. And, the value that an enterprise can get from software can be meaningfully larger than for the individual. 3) If you're past the PLG trap, the most important thing that a founder can do is to focus: become a solution-oriented product to reestablish product market fit and recharge velocity.
00:00 Introduction to Tom and Oliver
03:07 Overview of PLG at Dropbox
05:30 Overview of PLG at Asana
06:07 How to succeed in PLG end user acquisition phase
09:15 Tactics for Generating Awareness
10:17 Customer Expansion Phase
13:15 When Tension Arises Between PLG & Enterprise Security Needs
15:24 Security is an All Consuming Roadmap, not a Feature
18:35 How the Organization Shifts during the Transition from PLG to SLG
20:48 How Pricing Changes from PLG to SLG
26:22 The PLG Trap
28:03 Avoiding the PLG Trap
31:55 Value-Based Selling: Generalizable or Vertical/Use-Case Specific?
35:35 Atlassian v. Asana's Approaches
37:11 Advice for New Startups Pursuing PLG
38:22 Navigating from SLG to PLG
42:19 Resources for Founders
43:06 PLG, SLG & AI