20VC: Rippling's Parker Conrad on The Four Main Benefits From Building a Compound Startup | Why There Should Never Be a Trade-Off Between Speed and Quality | How Zenefits Gave Parker a Chip on the Shoulder and Why That is so Important?


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Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees’ payroll, benefits, expenses, devices, apps & more—in one place. To date, Parker has raised over $697M for Rippling from some of the best including Sequoia, Founders Fund, Greenoaks, Bedrock, Kleiner Perkins and Initialized to name a few. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund.

In Today's Episode with Parker Conrad:

1.) Entry in Startups and Zenefits:

  • How did Parker make his way into the world of startups?
  • How did Parker end up being kicked out of his own company, Zenefits? How did he respond?
  • How did that experience of being kicked out of Zenefits inspire him to build Rippling?

2.) Parker Conrad: The Leader:

  • How does Parker define "high performance"? How would Parker describe his leadership style today?
  • Why does Parker fundamentally disagree that with speed comes a trade-off in quality? How does Parker ensure Rippling does all things fast and to the best of its ability?
  • How would Parker break down his decision-making framework today? How does he decide what to prioritize vs not? How does he decide what to delegate vs not?
  • What are Parker's biggest insecurities in leadership today? How have they changed over time? What does Parker do to combat and mitigate them?

3.) Rippling: The Compound Startup

  • How does Parker define a compound startup?
  • What types of business do this verticalized approach work for vs not work for?
  • What does Parker believe are the 4 core benefits of this approach?
  • What are the single biggest challenges of building a compound startup?

4.) Rippling: The Economics:

  • How does this compound startup approach impact ability to cross-sell? How much net new ARR today comes from cross-sell?
  • What have been some of Rippling's biggest lessons on what it takes to do cross-sell so effectively?
  • How do the margin profiles differ across their different products? How have the margin profiles changed over time?
  • Why does Parker not believe that most startup margins are accurate?
  • How does the compound startup approach change the amount invested in R&D? How does that impact the fundraising requirements of the business?

5.) Rippling: The Partner Ecosystem:

  • How does Rippling think about building out the best partner ecosystem? What will it take for that to work?
  • Why do Rippling want to introduce services that compete with their own products? Why do they not only build their own?
  • How do the margins differ when comparing revenue share on partner products vs Rippling products?
  • What are the single biggest barriers to this partner ecosystem working?