Benyamin Holley is a self-described “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.

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”

Find Your Catalyst at https://findmycatalyst.com

Steve Heroux is a sales thought leader, author of The Sales Contrarian, and founder of The Sales Collective. Known for his humorous and no-fluff approach, Steve challenges outdated sales methodologies and champions a people-first philosophy. With roots in comedy and admiration for icons like Bob Ross and Larry David, Steve brings heart and honesty into the world of sales, coaching, and leadership.

1. "He didn’t paint to show you how good of a painter he was. He painted to show you how good of a painter you could be." – On Bob Ross’s influence and philosophy.

2. "Selling ice to an Eskimo doesn’t make you a great salesperson. It makes you an asshole." – On ethical, value-driven sales.

3. "You have to teach people how to swing like them, not like you." – On individualized coaching and leadership.

Steve Heroux joins the podcast to dismantle traditional sales myths, challenge robotic training, and advocate for purpose-driven selling. From detaching from outcomes to building self-awareness, Steve shares personal stories and strategies that ignite self-leadership and redefine success—proving that joy, ethics, and humility are the real game changers in sales.

• Robotic scripts kill connection; human presence builds trust.

• Salespeople should call audibles, just like smart quarterbacks do.

• Be you—your unique voice is your catalyst.

• Obsessing over quotas leads to burnout and misalignment.

• Focus on inputs you can control: preparation, practice, and care.

• Daily performance indicators (DPIs) matter more than KPIs.

• Real learning comes from being wrong, not being right.

• Self-awareness starts with admitting mistakes.

• Humor and humility unlock better performance.

• Use point systems to reward meaningful actions (thank you notes, learning).

• Make the work fun and joyful—like fishing or painting.

• Execution creates consistency; passion sustains it.

• One-size-fits-all training is outdated and ineffective.

• Great leadership develops the person’s swing, not the leader’s swing.

• Sales DNA assessments reveal unique strengths and blind spots.

"Why Sales Quotas Are Broken: Steve Heroux on Ethical Selling and Self-Leadership"

"Sales Without Scripts: Steve Heroux on Finding Your Voice and Letting Go of Outcomes"

"From Bob Ross to Sales Boss: Steve Heroux Redefines Success in Business"

Find Your Catalyst at https://findmycatalyst.com

Dale Dupree is the founder of The Sales Rebellion and a dynamic thought leader in modern sales. Known for his rebellious mindset and deeply human approach, Dale challenges traditional business thinking. He shares his love for nature, the power of curiosity, and his vision for Totality—a transformative experience that’s reshaping what a business conference can be.

1. “Change exists on a daily basis for me. So I don’t live in comfort or stagnation.”

2. “We can’t reflect on what we’re going to do—you have to do it, then reflect.”

3. “Totality is a mix of medicine and enlightenment. It’s about thinking much deeper about your existence.”

Dale Dupree reflects on his journey from urban life to the mountains, the importance of community and discomfort, and how these lessons shaped Totality 2025. He reimagines business experiences by emphasizing creativity, human connection, and inner exploration. This episode is about finding your catalyst by embracing unpredictability and authenticity.

• Leaving comfort zones leads to personal clarity and transformation.

• Dale’s story—from city life to mountain quiet—reflects this principle.

• Challenges force us to reevaluate what really matters.

• Dale values genuine interaction over polished personas.

• Small-town experiences gave him meaningful community bonds.

• Totality mirrors this by removing conference fluff in favor of real talk.

• Asking “what else is there?” breaks the cycle of complacency.

• Exploration is not just physical—it's emotional and intellectual.

• Rebelling isn’t destruction; it’s deep curiosity in action.

• Creativity is often undervalued in sales, but it’s a game changer.

• Totality brings hands-on, unexpected experiences to foster it.

• Real innovation starts by doing things differently—and with feeling.

• Pairing music and scent with moments enhances memory and meaning.

• Dale blends sensory cues and mystery to create Totality’s magic.

• People remember how you made them feel—not just what you said.

“Dale Dupree on Why Discomfort Is the Key to Living Fully”

“Totality 2025: Reinventing the Sales Conference Experience”

“The Rebellion Begins: Dale Dupree on Curiosity, Community & Creativity”