In this episode of The Effortless Podcast, Amit Prakash and Dheeraj Pandey dive deep into one of the most important shifts happening in AI today: the convergence of structured and unstructured data, interfaces, and systems.

Together, they unpack how conversations—not CRM fields—hold the real ground truth; why schemas still matter in an AI-driven world; and how agents can evolve into true managers, coaches, and chiefs of staff for revenue teams. They explore the cognitive science behind visual vs conversational UI, the future of dynamically generated interfaces, and the product depth required to build enduring AI-native software.

Amit and Dheeraj break down the tension between deterministic and probabilistic systems, the limits of prompt-driven workflows, and why the future of enterprise AI is “both-and” rather than “either-or.” It’s a masterclass in modern product, data design, and the psychology of building intelligent tools.

Key Topics & Timestamps

00:00 – Introduction
02:00 – Why conversations—not CRM fields—hold real ground truth
05:00 – Reps as labelers and the parallels with AI training pipelines
08:00 – Business logic vs world models: defining meaning inside enterprises
11:00 – Prompts flatten nuance; schemas restore structure
14:00 – SQL schemas as the true model of a business
17:00 – CRM overload and the friction of rigid data entry
20:00 – AI agents that debrief and infer fields dynamically
23:00 – Capturing qualitative signals: champions, pain, intent
26:00 – Multi-source context: transcripts, email threads, Slack
29:00 – Why structure is required for math, aggregation, forecasting
32:00 – Aggregating unstructured data to reveal organizational issues
35:00 – Labels, classification, and the limits of LLM-only workflows
38:00 – Deterministic (SQL/Python) vs probabilistic (LLMs) systems
41:00 – Transitional workflows: humans + AI field entry
44:00 – Trust issues and the confusion of the early AI market
47:00 – Avoiding “Clippy moments” in agent design
50:00 – Latency, voice UX, and expectations for responsiveness
53:00 – Human-machine interface for SDRs vs senior reps
56:00 – Structured vs unstructured UI: cognitive science insights
59:00 – Charts vs paragraphs: parallel vs sequential processing
1:02:00 – The “Indian thali” dashboard problem and dynamic UI
1:05:00 – Exploration modes, drill-downs, and empty prompts
1:08:00 – Dynamic leaves, static trunk: designing hierarchy
1:11:00 – Both-and thinking: voice + visual, structured + unstructured
1:14:00 – Why “good enough” AI fails without deep product
1:17:00 – PLG, SLG, data access, and trust barriers
1:20:00 – Closing reflections and the future of AI-native software

Hosts:

Amit Prakash – CEO and Founder at AmpUp, former engineer at Google AdSense and Microsoft Bing, with extensive expertise in distributed systems and machine learning

Dheeraj Pandey – Co-founder and CEO at DevRev, former Co-founder & CEO of Nutanix. A tech visionary with a deep interest in AI, systems, and the future of work.

Follow the Hosts:

Amit Prakash
LinkedIn – Amit Prakash I LinkedIn
Twitter/X – https://x.com/amitp42

Dheeraj Pandey
LinkedIn –Dheeraj Pandey | LinkedIn

Twitter/X – https://x.com/dheeraj

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