It takes guts, grit, and an uncommon dose of wisdom to lead a business team. Sameer Dholakia has all three qualities, plus two decades of leadership experience in enterprise software.

Dholakia is the CEO of SendGrid, one of the world’s premier email delivery services. SendGrid serves 50,000 customers and delivers 1.3 billion emails each day—more than double Twitter’s daily Tweet volume. In addition to its classic transactional email API, SendGrid more recently rolled out an email marketing product that has already been adopted by 5,000 users.

Dholakia is an experienced tech executive with a love of history and a passion for building strong teams and big businesses in the enterprise software industry. In our interview, he shares his most effective leadership habits, including the importance of humility, how to foster an outstanding company culture, and strategies for turning around a dire financial situation.

I’m so grateful Dholakia took the time to share so much of his knowledge and experience with the Powderkeg community, and I admire his resolve to always keep improving himself and his company. Connect with him on Twitter @spdholakia to share your appreciation, and enjoy the show.

In this episode with Sameer Dholakia, you’ll learn:

  • How you can begin using email marketing tools for your startup (13:40)
  • Strategies for launching a new product within your existing brand (21:27)
  • The only mistake in business you can’t recover from (33:26)
  • Why you should be a humble leader (36:30)
  • How to dig yourself out of a bad financial situation (42:48)
  • The two biggest challenges SaaS companies face (47:08)
  • How to create an exceptional company culture (53:54).

Please enjoy this conversation with Sameer Dholakia!

This episode of Powderkeg is brought to you by DeveloperTown. If you’re a business leader trying to turn a great idea into a product with traction, this is for you.

DeveloperTown works with clients ranging from entrepreneurs to Fortune 100 companies who want to build and launch an app or digital product. They’re able to take the process they use with early stage companies to help big companies move like a startup.

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Sameer Dholakia Quotes from This Episode of Powderkeg:

“It’s a lot easier to look back at history to help you predict the future than look into a crystal ball and try to guess.” — Sameer Dholakia

“Keeping your eye on your acquisition costs, sales and marketing spend relative to your profitability, and not burning a ton of cash in that process, is just good business.” — Sameer Dholakia

“There’s a deep humility that I find in reading the bios of the greatest leaders, because they all recognize it wasn’t just them.” — Sameer Dholakia

“The most important thing that you can do is figure out how to get the most leverage and impact from the precious hours and minutes that you’re working.” — Sameer Dholakia

Links and Resources Mentioned in this Episode:

Companies and Organizations:



Digital Marketing Association

McCormack & Dodge

Oracle Financial Services


Adaptive Insights


Reynolds & Reynolds














Startup Accelerators:


Software and Apps:






Shoe Dog


Dave Duffield

Marc Benioff

Joe Liemandt

Phil Knight

Mark Templeton

Did you enjoy this conversation? Thank Sameer on Twitter!

If you enjoyed this session and have 3 seconds to spare, let Sameer Dholakia know via Twitter by clicking on the link below:

Click here to say hi and thank Sameer on twitter!


What stood out most to you about what Sameer shares in this podcast?

For me, it’s how you can begin using email marketing tools for your startup.

You? Leave a comment below.


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