Words by
Carl J. Cox
AI is no longer optional in business. It is everywhere. Boards expect it. Teams ask for it. Vendors promise it will change everything. Yet most leaders feel frustrated because AI is not delivering the results they expected. In this episode of the Measure Success Podcast, hosted by Carl J. Cox, CEO of 40 Strategy and 40 Accounting, sits down with Eli Portnoy, co-founder and CEO of BackEngine, to unpack why that gap exists and how leaders can close it. This is not a conversation about hype. It is a grounded discussion about strategy, context, and execution.
The Problem With AI Today
Many businesses approach AI like a shortcut. They expect instant results without preparation. Eli explains that this mindset is the root problem. AI tools are smart, but they do not understand your business unless you teach them.
Most leaders ask AI to perform high-level tasks with little context. The result is generic output that feels useless. This leads teams to believe AI does not work, when in reality, the setup is flawed.
AI behaves like a new hire. A smart one, but still new. Without training, onboarding, and context, even the best hire cannot deliver value.
Context Is the Real Competitive Advantage
Throughout the conversation, one theme stays consistent. Context is everything.
Eli shares how BackEngine.ai was built around this idea. Instead of treating AI as a standalone tool, they feed it real customer conversations, sales interactions, competitor insights, and company-specific knowledge. This creates a system that understands the business at a deeper level.
When AI has context, it stops guessing. It starts producing insights that help teams sell, communicate, and execute better.
This lesson applies far beyond sales tools. Any leader using AI must first invest time in defining their message, their strategy, and their voice.
Why Go-To-Market Has Changed
The episode also explores how traditional outbound strategies have broken down. Email and LinkedIn outreach used to work because they were hard to do at scale. Today, automation has flooded these channels.
As soon as something becomes easy, it stops working.
Eli explains that trust has eroded because everyone is using the same automated playbooks. Buyers can spot inauthentic outreach instantly. The result is lower response rates and wasted effort.
The future of go-to-market is not more automation. It is smarter strategy. Leaders must focus on relevance, relationships, and intentional outreach.
Strategy Over Tools
Carl emphasizes a critical point for small and mid-sized businesses. Tools will not save you. Strategy will.
Private equity firms and large operators are investing heavily in content, data, and AI. Businesses that rely on old tactics without adapting risk becoming invisible.
This is not about doing everything. It is about doing the right things with focus and clarity.
Practical Advice for Leaders
Eli offers simple, actionable advice for leaders who want to start using AI effectively:
• Spend time documenting your business, voice, and strategy
• Use AI as a thinking partner, not a replacement
• Invest time before investing money
• Stay curious and test constantly
AI rewards leaders who experiment with intention.
Measuring Success Differently
Success is not just revenue or growth. Eli explains that usage, feedback, and learning matter more early on. Teams that integrate tools into daily workflows gain lasting advantage.
On a personal level, success also means building something you are proud of while staying present for family and life.
The Mindset That Wins
One of the most powerful ideas from this episode is humility. Eli believes leaders must treat everything as a hypothesis. Markets change. Channels break. What worked before may not work again.
The leaders who win stay humble, curious, and willing to adapt.
Final Thoughts
This episode is a wake-up call for leaders chasing AI without strategy. AI is not magic. It is leverage. Without direction, leverage only amplifies confusion.
If you want to build a business that lasts, strategy must lead every tool you adopt.
Listen to the full episode of the Measure Success Podcast and start using AI with clarity and purpose.
