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.

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?