Sameer (far left back row) and me (standing between Sameer and, yes, Jim Belushi) at a trade show for Trilogy in 1997

Ahoy Twilio SendGrid

6 min read February 4, 2019
Spotlight Infra

Last week, Twilio closed its acquisition of SendGrid, the global leader in cloud-based email delivery. As of market close on Friday, the merger valued SendGrid at $3 billion. For Bain Capital Ventures, this marks a milestone on a journey we began five years ago, when we invested behind Sameer Dholakia as he joined SendGrid as CEO.

However, this journey for me actually began 23 years ago… back to 1995, when I first met Sameer in the early days of Trilogy Software, an enterprise technology pioneer. I had the good fortune of joining Trilogy at the same time as Sameer, where we served on a product team together in early 1996. A decade before Sameer joined SendGrid, I also had the privilege of working with him as CEO of our portfolio company, VMLogix, which he led to an acquisition by Citrix.

I have met thousands of amazing people throughout my career, and Sameer is one of the truly special few. He is a world class leader and builder – smart, aggressive, driven to succeed, great with people, naturally charismatic, and unrelenting in pursuit of excellence. No surprise that employees voted him the best CEO of a small or midsize company in the country.

But when I think of Sameer, the words that immediately come to mind are different: kind, compassionate, humble, human, empathetic. Sameer is as a dear friend, a loving husband and father, a dedicated son and brother. Everyone who knows Sameer, knows that he is someone his friends can call at 2 am knowing he will pick up and get in his car or on the next plane.

Everyone wins

Throughout his career, Sameer has always focused on team success over his individual success. For Sameer, winning in business is a team sport and that not only includes the current members of an organization but the folks that came before.

When SendGrid went public, Sameer made sure that even former employees (and their spouses) who played important roles at the company were personally invited to join in the company celebrations.

During the Twilio negotiations (and the same was true when he sold VMLogix to Citrix), Sameer never once asked about his package or compensation – instead he was focused on the rest of the team and the broader set of shareholders and stakeholders. This has been a hallmark of Sameer’s throughout his life.

Dedication to family

Sameer is very devoted to his family – his two kids, his brother, his father, his wonderful wife Laura and many other relatives. Despite running a 400+-employee public company, Sameer always finds ways to spend time with his family, even if that means bringing his family to company events.

Sameer told me once that he calls his brother and his dad every single day, even if it’s just for a two-minute hello. As someone who had been speaking to my parents once a week at best, I began calling my parents every day as well. My dad passed away last year, but as a result of Sameer’s influence, I had the benefit of many thousands of calls and priceless moments with my mother and father that would never have happened otherwise.

Wearing his heart on his sleeve

Sameer will be the first to joke that he wears his heart on his sleeve. With his board or close advisors, Sameer is incredibly open and transparent with his ups and downs, his excitement and his frustrations – that’s who Sameer is. By being so open and vulnerable, Sameer engenders trust and forges deep connections. With Sameer, you know you are truly in the trenches with him no matter what, for better or for worse. There are plenty of examples of great leaders who are either cold and uninspiring, or who lead with unending positivity and cheerleading. Sameer’s success, by contrast, is firmly rooted in the emotional connections he makes with his teams and with his business relationships.

In today’s tech universe, where it seems blockbuster success always requires a dark side, where it’s easy to believe you need to lose your humanity to win, Sameer bucks the narrative. His values are the foundation of his success, not an impediment. Sameer demonstrates that a different kind of leader can create massive value for shareholders and employees, while staying true to a set of principles that are rooted in human values not just shareholder value.

Delivering the future

With SendGrid, Sameer had the benefit of joining a great company, where the founders — Isaac Saldana, Tim Jenkins, and Jose Lopez – built a modern API-driven platform for sending email. Through a developer-first community approach, Isaac and his team created a very efficient distribution model. The business didn’t require sales people and benefited from the fact that SendGrid’s revenues rose as our customers expanded (and naturally sent more emails!), resulting in incredible organic growth.

Under Sameer’s leadership atop this amazing foundation, SendGrid’s growth accelerated as the company strengthened its market position, launched new products, and continued to welcome new Gridders to its team across Denver, Irvine, and Redwood City.

In 2017, SendGrid went public on the New York Stock Exchange and in 2018, SendGrid and Twilio announced the $3B transaction. In less than five years, SendGrid’s value has increased nearly 15x. This is an amazing accomplishment by the entire team, and we are proud to have been part of this incredible journey.

Sameer and me twenty years later in 2017, on the floor of the New York Stock Exchange during SendGrid’s IPO

Over the course of my professional life, the one individual with whom I have worked with the longest has been Sameer: at Trilogy, VMLogix and now SendGrid. Sameer – Thank You! I am so lucky to have worked with such a close and dear friend, and to have learned so much from you about business, leadership, and friendship. Your positive approach to life, kindness and empathy, deep relationships, and innate spirit are a wonderful example for all of us. I am eager to see the new heights to which you, the SendGrid team, and the Twilio family will achieve in the years and decades ahead.

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