Repositioning is one of the hardest things a marketing team has to do. The words aren't the hard part. The hard part is doing it under pressure, with a lot of eyes on you, after something has already happened publicly.
In 2019, Twilio acquired SendGrid in an all-stock deal valued at around $2 billion. For years, Twilio had positioned itself as the future of communications through SMS, voice, and video. We were vocal about it. We'd literally say, "Email is dead."
The Narrative Had to Change Overnight
The marketing team got to work immediately. The new story needed to make sense of the acquisition and reposition Twilio as a true all-in-one communications platform. The message became: every business communication channel, SMS, voice, video, and now email, together in one place for developers.
For me, that meant rebuilding the corporate pitch deck from the ground up and designing a new marketecture showing how these pieces fit into a unified platform.
Storytelling Alone Wasn't Enough
Repositioning the narrative was only half the work. We also had to prove to investors, the board, and the market that this integration made business sense.
A small tiger team formed: myself, a colleague from Operations, and someone serving as Chief of Staff to our CRO. We built a cross-sell plan with aggressive targets: $20 million in new revenue from selling Twilio products into the SendGrid customer base, and $5 million from selling SendGrid products into the Twilio base, all within the first year.
In Q1, we hit the overall pipeline targets. We also learned that broad campaigns with small incentives to try the other company's products weren't generating enough pipeline for the sales team.
The Real Lesson: Same Use Cases, Different Base Doesn't Work
We were selling the same use cases to a different customer base. Twilio's API customers used SMS for delivery alerts and notifications. SendGrid's customers used email for the exact same types of notifications. A company already using SMS for alerts had no obvious reason to add email for the same purpose.
Three things changed our approach:
- Segmentation. We stopped promoting the same message to everyone and identified specific use case gaps in each customer's business. If a SendGrid customer was already using email for notifications, we targeted adjacent needs like SMS marketing or two-factor authentication.
- Positioning refinement. SMS is better for urgent, time-sensitive communication. Email is better when the message requires recall, like an order receipt. We tied channel value to real customer journeys.
- Thought leadership. We invested heavily in content that brought the multi-channel story to life with real examples and tangible use cases.
The Harder Challenges Were Operational
Different Salesforce instances for sellers at both companies. Undefined payout structures and quota attainment rules. Building trust with a team at an acquired company when the relationship is still new.
When you can't accurately track new pipeline, or you're working through duplicate accounts across two CRMs, sellers lose patience and shift focus to more immediate revenue drivers.
What I'd Tell Anyone Facing This
Map out everything that could go wrong before you start. It was the first time for all of us leading a change at that scale.
Repositioning after an acquisition is a business transformation exercise, and the storytelling, revenue strategy, and operational rigor have to move together.