In the month before Twilio’s acquisition of SendGrid closed, we conducted an integration survey with all of our employees to understand where they stood. For all of my folks, the day to day post-acquisition promised to be just about the same as the day to day prior to acquisition. They would work for the same people doing the same job in the same way for the same pay and all of this had been communicated. The merging of the two companies, however, was exceptional news for us as it helped us realize our company’s 10-year vision overnight! Naturally, I expected very little angst to show up on the survey and, quantitatively, that proved to be true. Engineering had the highest engagement in the company. The qualitative data, which showed up in the 244 comments told a different story. Many were apprehensive. (Side note: the qualitative comments always give color to the quantitative data. All leaders should read every survey comment every time.)

I recently came across the email that I sent out to the team to calm their nerves the night before the acquisition closed. Quoted in part below, it carries a point from which many leaders could benefit. We are all toughened into what we deal with day in and day out. Given the number of different jobs being done within any company, that means we are all toughened into many different things. What seems like a big deal to me might not matter to you. When somebody panics and that is confusing or seems silly to you, it might just be because you’ve become desensitized. The solution is simple — start with some empathy and follow it up with a whole lot of conversation.

From: Craig
To: Engineering-all

Last night I spent a few hours pouring over the results of the integration engagement survey and it painted quite a picture.  Quantitatively, engagement is up almost across the board and for the first time in my professional career, I find myself leading the most engaged department in the company.  (Engineers by nature see all the areas for improvement and tend to score lower on such  measures.).  What this tells me is that you all see the amazing opportunity in front of us.  We really do get to press fast-forward on our vision of becoming the world’s most trusted customer communications platform.  Overnight we pick up all the communication channels our customers care about…. There are truly exciting times ahead!

At the same time, I read all 244 Engineering comments on that survey and got a fuller view.  While we are all mostly excited, it is impossible to ignore the anxiety around change and uncertainty.  Despite communicating that there are no changes on the horizon, over a hundred comments related to stress around not knowing what changes are coming and whether those changes would be Good or Bad.  This really struck me and exposed one of my blind spots.

As a senior leader, the vast majority of my time is spent working on things that never ever come to fruition.   As one such example, you all know about the major acquisition that took place last year but almost none of you know about the multiple that came close.  I (and many of my leaders) are toughened into change and uncertainty because we live with it every day.  Our jobs are to explore the possibilities knowing that we must choose the best path among them.  We don’t share all the possible outcomes as they are in flight because it would only cause stress and churn.  It is a lot like living on a roller coaster that crashes more often than it returns safely to pick up new passengers.  As leaders, we get on this ride every day because we owe it to you.  You deserve a clear path that we know will land safely and that will feel meaningful.  Our shareholders deserve their returns.  Our customers deserve our very best.  Tomorrow is no different for us.

The majority of you in Engineering, however, build things that are real.  Tests pass today that didn’t yesterday.  Stories get done.  Trainings happen.  (Career Development Plans) get filled out.  These things that you do send trillionS of emails, help our customers reach their customers in meaningful ways, and drive revenue for SendGrid.  The things that you do every day get us closer to our vision.  There is less uncertainty in that.  Tomorrow is different — you see yourself getting on a roller coaster.  We promise it’ll return you safely and that we’ve been on it before and that it’ll be a lot of fun.  That reassurance doesn’t take the butterflies away.  That is completely normal.

The best reassurance, IMO, will be through transparent communication.  In the coming weeks, I’ll make sure to host multiple listening posts where folks can come to ask questions and share concerns.  Where I don’t have answers, I’ll be frank and where I do, I’ll happily share them.  We’ll get through all this change together.

<Redacted — addressing specifically voiced concerns./>

I am incredibly excited about the opportunity we have and I know that y’all are the right team for all the joys and the challenges that sit in front of us.  There is nobody I’d rather have with me on this journey.   I’ll try my darnest to communicate as things become more clear.  Please do not be shy about hitting your leadership (myself included) up with any questions/concerns you might have.  If we remember to assume positive intent and commit to continuing to talk, there is no difficulty we cannot get through together.


Over the next month, I hosted half a dozen listening-post sessions. A lot of people showed up for the first couple sessions and they felt safe to voice their concerns, rational or not. In return, their questions and concerns were addressed with full candor. The last few sessions were much less well attended. It turns out that once people had been heard and reassured, they agreed that it must not be scary to be acquired. And they had work to get back to.