GTM Engineering Explained: Automation, AI & Fearless Thinking with Benyamin Holley

Benyamin Holley is a “GTM engineer” who blends technical tools and creative problem-solving to revolutionize go-to-market strategies. With a background in music tech and a passion for scrappy, AI-driven workflows, Benyamin brings a fresh, practical approach to solving sales and operations problems. Currently at Sift, he’s helping shape how startups use automation to scale smarter, not just faster.

1. "Sales is a thinking process. And if you think well, you can build better systems."

2. "Less is more — I don’t want more leads; I want better ones."

3. "Fear of being wrong holds people back. But if you're doing something good, the world conspires in your favor."

Benyamin Holley joins the show to share how he's redefining sales and go-to-market strategies using AI and automation. From his roots in music education tech to pioneering GTM engineering at Sift, Benyamin dives deep into what it means to proactively solve problems, embrace tools like Clay, and find true product-market fit.

🔑 5 Key Takeaways 1. GTM Engineering Is a Thinking Process

• GTM (go-to-market) engineering isn't just a buzzword—it's a mindset.

• It involves problem-solving across the sales funnel using AI and automation.

• You don’t need to be a coder, just scrappy and optimistic.

2. Start with the Right Fit

• Whether it's customers, culture, or tools, fit reduces friction.

• Good fits feel like "no-brainers"—they flow without forcing.

• If you’re constantly battling resistance, it may not be the right match.

3. Fear Stops Progress

• People often hesitate to act because they fear being wrong.

• Startups thrive when people tackle problems without waiting for approval.

• Building confidence through small wins helps overcome this fear.

4. The List Is the Strategy

• Outbound success depends on building a high-quality, well-qualified list.

• Tools like Clay help isolate the right leads with fewer but better targets.

• Relevance in outreach increases connection and reduces noise.

5. Let Robots Do the Busywork

• Automation isn’t about replacing humans, but enhancing them.

• Benyamin shares how AI tools manage waitlist follow-ups automatically.

• Freeing time from manual tasks lets people focus on meaningful conversations.

“From Music Tech to GTM Engineer: Benyamin Holley on Sales Innovation with AI”

“Why Less Is More in Sales: Benyamin Holley’s Playbook for Smarter Outreach”

“GTM Engineering Explained: Automation, AI & Fearless Thinking with Benyamin Holley”

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