SaaStr 199: Betterment Founder, Jon Stein on The 3 Key Roles For A SaaS CEO, How To Retain Startup Culture As You Scale Past Startup Stage & The Most Telling Questions In Candidate Interviews To Stress Test Culture-Fit

Jon Stein is the Founder & CEO @ Betterment, the online financial advisor built for people who refuse to settle for average investing. To date, Jon has raised $275m in VC funding with Betterment from the likes of Bessemer Ventures Partners, Menlo Ventures, Kinnevik and Francisco Partners, just to name a few. Prior to founding Betterment, Jon spent 4 years as a consultant at First Manhattan Consulting Group where he really honed his experience in working with banks and brokers including revitalizing a bank in Australia with the launch of a best-in-market auto-finance offering, resulting in 50% lift to revenue. As a result of his phenomenal success with Betterment Jon has won many awards including Fortune’s 40 Under 40.

In Today’s Episode We Discuss:

• How Jon made his way into the world of startups and came to found democratize the world of investing with Betterment?
• When does Jon believe is that critical moment when the founding team must hire their first employee? What is the right strategy to build the candidate pipe for hiring those first employees? Where does Jon see many go wrong here? What 1-2 questions does Jon always find the most enlightening to ask in the interview?
• Once hired, what have been some of Jon’s biggest lessons in terms of optimising the onboarding experience and the first 60 days? How has their process changed over time? How does Jon determine when a stretch candidate is a stretch too far? If so, what does Jon believe is the right way to let go of an individual?
• What does Jon believe to be the 3 core roles of the CEO in any company today? From those, what has Jon found most challenging? What did he do to level up and overcome the challenges? How does Jon approach transparency with the team in delicate cases like fundraising and acquisition etc?
• With the team and product in place, scale can occur, what are the 2-3 things that all companies need to focus on when product market fit has been achieved? How does Jon determine when is the right time to really put the pedal to the metal and scale?

Jon’s 60 Second SaaStr:

1. Jon’s favourite book and why?
2. What does on know now that he wishes he had known at the beginning?
3. What is Jon’s biggest strength and weakness?

Read the full transcript on our blog. 

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Jason Lemkin

Harry Stebbings

SaaStr

Jon Stein