We were happy to welcome Sameer Dholakia as SendGrid’s new CEO at the end of September. As we approach the close of the year, we were excited to talk with him about his new role, what his first 30 days on the job were like, and what he sees as priorities for SendGrid moving forward.
Q: You’ve been a CEO of a startup before and an executive at a large enterprise IT company. How does that experience carry over to your new role as the chief executive of SendGrid?
A: SendGrid is at a great inflection point. I’m excited to help carry on this entrepreneurial fire that will allow us to continue the success that we’ve had to date. As we go forward and continue to scale the business as a growth stage company, there are certain learnings, specifically around scale operations, that we can benefit from. Where I can lend my experience is in having seen some of those challenges before. I can help make sure that those obstacles don’t become bottlenecks to our continued growth.
For example, in a smaller scale company, it’s easier to get everyone in front of a whiteboard, come up with ideas, and get software shipped quickly. When you start to scale, the software you’re developing gets more complicated, and the number of people involved in the process gets bigger.
Another challenge as a company scales can be around creating a line of sight between what an employee does every day and the company vision. The company mission is way easier when you’re twenty people in the room and the CEO and the management team are sitting right next to every employee in the company.
So you have to be really thoughtful about what I call your “communication architecture”—how are we going to intentionally design communication flows that get information around vision and priorities from management to employees? And then how do we get alignment from different functional groups across the organization, and also feedback from the employees all the way back up through the leadership ranks, so that we are course correcting based on the insights of the people that are closest to the work?
Q: SendGrid has a very unique and renowned company culture. How can this be maintained and even enhanced as the company grows?
A: The SendGrid culture really resonated with me, and was an important part of why I wanted to come join the team. As companies grow, cultures need to get maintained, and sometimes it gets refined over time. We have a terrifically strong culture that’s really well embedded in the company.
I deeply believe that the CEO’s job is as much about being a Chief Cultural Officer than anything else. So it’s important for me that I do a good job of continuing to reinforce and protect that culture. I view that as one of my responsibilities.
Q: You live in the Bay Area and travel to SendGrid’s offices each week. What have you learned about working with teams that are spread across different time zones?
A: It’s fairly rare to have all of what you do in one particular location nowadays. So working across offices has to be a core competency for most world-class organizations.
From an operating perspective, it does make it more difficult though, because you don’t have everybody in the same room. At SendGrid, we are really good at intentional communication. We have our weekly “All Hands” meetings where we connect all the offices with video and people feel connected. So, despite the fact that we have executives spread across three or four different locations, it’s a high-functioning team because of the very intentional and explicit investment in communication.
However, I still feel that there is no replacing being in person—that matters a lot. That’s why I continue to spend most of my time in each of our offices, so I can get to know the company, and the organization, and the people.
Q: Why did you decide to take on this role at SendGrid?
A: There are both rational and emotional reasons for me taking the role here. What I loved about the SendGrid opportunity was that it allowed me to bring together this entrepreneurial startup skill set and this larger company skill set, to help the company scale. It just feels like I’ve been training for twenty years for this opportunity with SendGrid—to really bring what I’ve learned across those different experiences to this inflection point that I believe SendGrid is at.
One of the other things I loved about it is the core business itself. We just have an amazing solution in the market that will only continue to grow. I love the market that we’re in, and I love that we are a market leader in what we do. I genuinely believe that there are so many opportunities still ahead for SendGrid to continue to accelerate our business and most importantly, help our customers. We’ve only scratched the surface.
Another big part of my decision was on the people side—just how the culture resonates in every person I’ve met at SendGrid. Everyone exemplifies that culture. It isn’t just words on paper. This is how SendGridders are—they love SendGrid. They bleed SendGrid Blue. They are friends in addition to being colleagues. They don’t think about SendGrid as just a job; they love this place. And for a guy like me looking at coming in, that’s gold.
Q: How were your first 30 days at SendGrid?
A: Frenetic. Exciting. Exhausting. Those are the emotions. I have loved learning about the business from our team—what do they see as core to our success and what do I need to do to maintain and protect those things. My job and responsibility is to help support those changes.
It’s been awesome being a sponge—learning, listening, and beginning to connect the dots between the conversation and discussions. I can start to see the patterns and see where this can go.
Q: What do you see as the biggest opportunities for SendGrid? What are your top priorities?
A: There are things in our core business that we have tremendous opportunity to keep innovating around. We have delivered 15B emails a month at scale for some of the largest brands in the world. It’s an incredible starting point and there’s so much we can do to enable our customers with insight around their deliverability.
We can continue to innovate to serve our customers better than we ever have. We’re at the beginning of a huge opportunity for SendGrid to offer our customers a more complete email solution.
Q: The email landscape is constantly changing. As you’re getting to know the industry, what has been one of the more interesting email facts that you’ve learned?
A: Just how structured the industry is, and its response to fighting spam. Learning about some of the challenges related to deliverability and compliance has been very interesting. I was thrilled to hear about how much SendGrid has invested in helping our customers with that challenge. And in making sure that we’re one of the good guys, and we’re helping our customers be among the good guys.
Q: What kind of email recipient are you? Are you inbox zero, with all of your emails read? Or inbox overwhelmed, with lots of emails that are unread?
A: There is no question that I’m inbox overwhelmed. I promised myself, when I came to SendGrid that I was going to change my ways…and it turns out that a leopard cannot change its spots.
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