Transforming Enablement with AI Coaching

So I finally got to sit down with Ioanna Mantzouridou Onasi CEO of Dextego

Ioanna’s passion for understanding human motivation, coaching, and technology shines through her story—from her psychology roots to becoming a startup leader.

We explored the gaps in traditional sales training, particularly how ineffective and biased role plays are, and how Dextego leverages AI to deliver timely, personalized coaching that actually works. She shared her take on the human-AI balance, emphasizing that technology should optimize human performance, not replace it. Dextego aims to coach reps throughout the sales cycle, reduce ramp-up times, and help them deliver value-driven messaging to the right persona at the right time.

Ioanna also highlighted how AI can shift enablement from reactive to proactive, shorten sales cycles, and elevate reps with gamified, real-time learning. Lastly, we discussed the broader impact of AI on business workflows, emphasizing change management and the importance of clear strategies.

• AI Coaching Gaps in Sales Enablement: Traditional role plays are outdated and biased. Reps need coaching that aligns with real-world scenarios. First-time managers often lack proper coaching support.

• Dextego’s Core Value: AI coaching platform that blends company data, sales best practices, and human expertise to deliver targeted, real-time coaching. Use cases span onboarding, consistent messaging, and deal support.

• Results and Impact: Shortens sales cycles by 30% on average. Drives reps to deliver persona-specific value props, not scripts.

• AI as an Optimizer, Not a Replacer: Ioanna believes in improving human performance while automating low-value tasks. Sales remains a human-centric art of communication.

• Future of Enablement: AI agents will focus on specialized coaching areas like negotiation, discovery, and methodologies. Continuous feedback and tailored coaching styles are key.

• Upcoming Trends for Leaders: Companies need to rethink their tech stacks and decide what tools are foundational vs. integrative. AI tools can transform workflows, but change management is critical.

1. On Coaching Gaps: “We found that the first-time managers—BDR managers, for example—just don’t get the training they deserve.”

2. On the Power of AI: “The goal is to deliver the right coaching at the right time. Reps don’t have time to wait for feedback—AI makes it immediate.”

3. On Sales Enablement Problems: “You tell a rep, ‘If the customer says A, say B,’ but the customer always says C or D.”

4. On Human vs. AI Balance: “Sales is the art of communication. If we lose that, what are we as a civilization?”

5. On Dextego’s Results: “On average, companies shorten their sales cycles by 30% when they use our platform.”

6. On Using AI Responsibly: “Founders have a responsibility to create solutions that improve well-being, not just replace jobs because they can.”

7. On the Bigger Picture: “It’s not about trying 10 pilots. It’s about being strategic and supporting yearly goals with real ROI.”

This conversation was all about transforming sales enablement into something modern, effective, and human-first. Ioanna’s ...