Bobby Napiltonia, Serial Founder
Check out our Member Brief with Bobby Napiltonia here.
Q: Can you share a little about your journey and background?
Bobby Napiltonia: I’ve spent 37 years in the tech industry, beginning with distribution roles and evolving through significant positions at Salesforce, State Software, and Twilio. I often describe myself as the ‘Forrest Gump’ of the industry—present at key moments that shaped tech as we know it.
Q: What experiences do you think were most formative in your career?
Joining the largest RCA and Whirlpool distributor in America laid my foundation in understanding distribution. That experience, combined with my roles at Salesforce and Twilio, showed me how pivotal go-to-market strategies and distribution models are to a company’s success.
Q: Can you tell us more about your time at State Software?
At State Software, we worked on making the web stateful at a time when it was stateless. This led to the creation of JSON, which has become integral to the web today, even if it wasn’t immediately financially successful for us.
Q: What lessons did you take from your time at Twilio?
At Twilio, I learned the importance of pricing strategies and market positioning. We struggled initially, but once we found the right pricing model, we scaled from $5 million to $178 million in 18 months. It taught me that strategic adjustments in pricing can unlock growth.
Q: What are you currently focused on?
I’m working on understanding how generative AI and other innovations will shape the next decade. The industry is moving towards solutions that reduce complexity—from ‘no software’ to ‘no applications,’ focusing on seamless user experiences.
Q: What motivates you most in your current work?
Relationships and the people I collaborate with have always been my greatest motivation. The ability to engage with others and share insights continues to drive me forward.
Q: What advice would you give to new founders?
Talk to people and learn from their experiences. Don’t assume you know everything—listening can reveal the distribution and go-to-market strategies that are essential to success.
Q: What challenges do you foresee in the near future?
Balancing automation with human input will be critical as we move forward, particularly with advancements in AI. We need to make sure we use these technologies ethically and in ways that benefit society as a whole.
Q: What key insight would you like to share?
Adaptability is crucial. The tech landscape evolves rapidly, and the ability to pivot while staying grounded in strong fundamentals is essential for enduring success.
