SaaStr 218: Twilio Founder, Jeff Lawson & SendGrid CEO, Sameer Dholakia on Why Developer First Is A Maturation In The Supply Chain Of Software & Why With Software Innovation Costs Being Lower Than Ever, Operators Must Maximise The Number of "At Bat" Oppor

Jeff Lawson is the Founder & CEO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Jeff, prior to founding Twilio, Jeff was the Founder & CTO @ Nine Star Inc and enjoyed a spell at Amazon as a Technical Product Manager.

Sameer Dholakia is the CEO @ SendGrid, the category leader in email delivery, reaching half of the world’s digital users every 3 months. Last year Twilio acquired SendGrid bringing email into one seamless customer engagement platform. As for Sameer, prior to joining SendGrid, he spent 4 years at Citrix, where he drove the company’s product strategy for cloud infrastructure and server virtualization. Sameer joined the company in 2010, when Citrix acquired VMLogix, where he served as CEO and doubled revenues during each year of his tenure. Before that, he worked for 12 years at Trilogy, where he held key leadership roles helping the company grow from a start-up to a $300 million business.

In Today’s Episode We Discuss:

• How Jeff came to found Twilio and what was that a-ha moment for him? How did Sameer enter the world of SaaS and come to be CEO @ SendGrid?
• How did Jeff and Sameer assess the culture fit between the 2 companies when deciding whether or not to join forces? How did they formulate and approach creating a new set of values with the 2 companies coming together? How do they distinguish between culture and values? How can leaders both be authoritative and vulnerable simultaneously?
• What does Jeff mean when he says, “the developer first approach is a maturation of the supply chain of software”? How has Jeff seen his original thesis for “developer first” evolve and change with time? What does truly special customer experience look like in the developer first model?  
• In terms of product strategy, how do Jeff and Sameer approach when is the right time to release a second product? What does Jeff mean when he says, “you have to maximise the number of at bat opportunities you have”? Why does Sameer think that SendGrid waited too long to release additional product lines? What were his core learnings from that?
• How do Jeff and Sameer think about what what truly special leadership looks like today? How do they approach speaking so that people will remember? What are some of their biggest tips to aspiring entrepreneurs with regards to that and team empowerment? Why do both Jeff and Sameer believe that so much of the management wisdom today is outdated?

60 Second SaaStr:

1. What do Jeff and Sameer know now that they wish they had known at the beginning?
2. The book they have gifted most often and why?
3. What does it take to truly be a great board member?
4. What do the next 5 years look like for Twilio? How big could it get?

Read the full transcript on our blog.

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Jason Lemkin

Harry Stebbings

SaaStr

Jeff Lawson

Sameer Dholakia