There’s a quiet panic happening in go-to-market teams right now. AI is moving fast. Automation is everywhere. Email volume is higher than ever. And yet… response rates are slipping, attention spans are shrinking, and differentiation feels harder than ever.
So what happens when your competitive advantage becomes everyone else’s baseline?
That’s exactly what Amy Cook, CMO and co-founder of Fullcast, set out to explore in her conversation with Kris Rudeegraap, co-CEO of Sendoso. Together, they unpacked the evolution of modern sales and marketing—from the early mail merge days to AI agents—and why the future belongs to teams who know how to blend automation with authentic human connection.
If you’re leading a GTM team, investing in ABM, or trying to figure out how AI fits into your strategy without losing the relationship piece, this conversation is both validating and a little provocative in the best way.
Here are some highlights from that interview.
Amy: You started Sendoso over nine years ago. What sparked the idea?
Kris: I spent about a decade in sales. Around 2014, I was early to mail merge. I could book meetings so easily—90% email response rates. It felt like magic. Then it stopped working.
Email sequencing tools exploded. Suddenly what made me different was available to everyone. My competitive advantage disappeared overnight. So I asked myself: What can’t be automated?
That’s when I started manually sending gifts. If I heard a dog bark on a call, I’d send a dog toy. I’d grab swag from marketing closets. I’d handwrite notes after demos. It worked incredibly well, but it was painful. Spreadsheets. Expense reports. Tracking links. Eventually, I realized: why isn’t there a platform to operationalize this? That was the beginning of Sendoso.
Amy: Back then, digital felt saturated. Fast forward to now—what’s changed?
Kris: It’s ironic. A decade ago, I thought digital was saturated. Now it’s exponentially louder. And I’m not anti-digital. Digital works. But a digital-only strategy? That’s where teams struggle.
You need email.
You need ads.
You need content.
You need direct mail.
You need field events.
Modern go-to-market isn’t about choosing channels. It’s about orchestrating them. The companies winning today are creating attention and then building relationships.
“I believe in the power of digital—but you can’t have a digital-only strategy.” –Kris Rupeegraap.
Amy: Let’s talk AI. What’s your hot take on where go-to-market is headed?
Kris: The most important role emerging right now? The Go-To-Market AI Engineer. Not someone who just runs outbound tools. Not someone provisioning Salesforce access. Not someone building CRO forecast reports. I’m talking about someone obsessed with AI agents and agentic workflows. Someone who understands APIs, data warehouses, automation frameworks. Someone who can translate human tasks into specs that AI agents can execute.
“The go-to-market AI engineer could be the most critical role over the next few years.” –Kris Rupeegraap.
That role could redefine GTM over the next few years. And I think it’s underestimated.
Amy: For leaders trying to justify ABM and gifting investments, how should they think about ROI?
Kris: There are three ways to think about ROI . . .
