SaaStr 200: Should SaaS Startups Start At SMB and Scale To Enterprise or Vice Versa, What It Takes To Make The Transition From CTO To CEO & The Right Way To Think About SaaS Pricing Today With Brad Birnbaum, Founder & CEO @ Kustomer

Brad Birnbaum is the Founder & CEO @ Kustomer, the first intelligent platform for customer experience that enables you to know everything about every customer. To date Brad has raised over $38m in funding for Kustomer from some of the very best in the SaaS business including Tomasz Tunguz @ Redpoint, Ed Sim @ Boldstart, Canaan Partners, Box Group and Social Leverage just to name a few. Previously he was the Co-founder of Assistly, which was acquired by Salesforce and became Desk.com. Prior to that, he was CTO for Talisma and Co‑founder & CTO of eShare Technologies. In addition, Brad was also the CTO @ Sean parker’s Airtime and VP of Engineering with Salesforce. In Today’s Episode We Discuss: How Brad made his way into the world of customer experience and SaaS over 20 years ago? This is Brad’s 4th time at the roadshow, what does Brad believe are the core benefits of repeat entrepreneurship? How did his prior experience change his operating mentality with Kustomer? What has he done differently this time? What worked and he has kept the same? Brad has made the transition from CTO to CEO, how did he find this transition? What were some of the most challenging elements? What have been some of the biggest surprises? What advice would Brad have for other CTOs who have made or are thinking about making the transition? Brad initially served SMBs with Kustomer but now primarily focuses on mid-level, what would Brad’s biggest advice be when it comes to finding the right go-to-market strategy for you? How did their transition alter their approach to pricing, product, messaging and distribution? Where does Brad see many people go wrong on go-to-market? Brad’s 60 Second SaaStr: What does Brad know now that he wishes he had known at the beginning? When is the right time to pour fuel on the company fire? What would Brad most like to change in the world of SaaS? 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 SaaStr Brad Birnbaum This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com