In an era where inboxes are overflowing and attention spans are shrinking, SMS has quietly emerged as one of the most effective yet misunderstood tools in a modern go-to-market (GTM) team’s arsenal.
In our latest GTM Innovators episode, I sat down with Phil Portman, founder and CEO of Textdrip, to talk all things business texting. What started as a conversation about automation quickly evolved into a deep dive on trust, transparency, and the subtle art of sending the right message at the right time.
1. The Power and Pitfalls of Business Texting
Texting isn’t just a new channel; it’s a different one. The immediacy of SMS is unmatched. According to Phil, “The response rate on texting is 45% compared to 6% in email.” And most texts are read within 90 seconds.
That’s an incredible opportunity, but also a liability.
“Text messaging is, ‘Hey, I got this thing for you right now.’ It’s a powerful tool, and it needs to be used appropriately,” Phil explained.
Unlike email, where a misfire can be ignored, a poorly timed or irrelevant text can instantly damage the relationship. Which leads to the next key point:
2. Intent Beats Automation Every Time
The power of SMS lies in contextual timing and authenticity, not volume. Phil’s team at Textdrip has built intent models that help clients scale conversations without sacrificing human trust.
“AI does the grunt work, sorting, tagging, flagging. But humans still close the deal,” Phil said.
And here’s the warning: “Don’t try to trick your customers into thinking they’re talking to a human when they’re not. That’s how you lose trust instantly.”
Intent-based automation means responding to signals, not blasting cold outreach. It means using AI to help assist, not impersonate.
3. Specificity and Segmentation Win
Phil didn’t just preach philosophy; he shared real tactics. One of his most actionable pieces of advice? Stop sending generic messages. Instead, use tags, merge fields, and behavior-based triggers to create individualized outreach that feels timely and real.
“You’re not sending a message that says, ‘I have homes in your area.’ You’re saying, ‘That four-bedroom, two-bath you want just hit the market.'”
That level of personalization isn’t just possible. It’s scalable with the right automation strategy. Textdrip even bakes in “ghosted” follow-up drips that automatically continue the conversation if a contact goes quiet, while gracefully stopping if they respond.
Want the Full Conversation?
Phil also touched on SMS cost, compliance pitfalls, the future of AI in messaging, and how a 54-acre horse ranch keeps him balanced as a founder.
Watch or listen to the full episode of GTM Innovators with Phil Portman here: Texting with Intent – Phil Portman on Smarter SMS for Modern GTM Teams
Whether you’re just starting to explore SMS in your GTM strategy or looking to optimize what you already have, this is one conversation you won’t want to miss.