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

Share your thoughts :

Have questions, comments, or ideas for future episodes?
Email us at EffortlessPodcastHQ@gmail.com

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In this episode of The Effortless Podcast, Amit Prakash sits down with Abhay Parasnis, Founder and CEO of Typeface, to explore how AI is reshaping marketing, creativity, and entrepreneurship.

Abhay reflects on his incredible journey from building foundational internet technologies at IBM, leading Microsoft’s Azure transformation, driving Adobe’s shift to the cloud, and now launching Typeface to personalize content creation at scale through generative AI.

He opens up about what it really means to start over after corporate success, the evolving definition of product-market fit in the AI era, and why speed, curiosity, and the beginner’s mind are the most important superpowers today.

Amit and Abhay discuss the “AI slop” problem, steering powerful models with context, unlearning corporate habits, and how the next generation of AI agents will move from orchestration to closed-loop intelligence.

Key Topics & Timestamps

00:00 – Introduction
01:15 – Abhay’s journey: from IBM & Microsoft to Adobe and Typeface
05:40 – The beginner’s mind and the art of reinvention
10:25 – Leaving Adobe to start from scratch
15:30 – Risk, ego, and the emotional side of entrepreneurship
21:10 – Redefining product-market fit in an AI-driven world
27:45 – The “continuous recalibration” mindset for startups
33:30 – Solving “AI slop” with brand context and personalization
39:20 – Engineering challenges behind Typeface’s AI platform
46:00 – Why social engineering is as hard as technical innovation
51:15 – Lessons from Adobe & Microsoft: what to keep and unlearn
56:40 – Steering AI systems: the new critical skill
1:02:05 – Counterintuitive truths about creativity and automation
1:07:10 – Democratized AI vs. expertise — the paradox of access
1:11:00 – The future of marketing AI and closing thoughts

Host:

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

Guest:

Abhay Parasnis –Abhay Parasnis is the founder & CEO at Typeface.ai - a leading Enterprise Generative AI company. Abhay is also a board member at Dropbox & Schneider Electric. Additionally, abhay is an active early stage investor & advisor for various AI startups including Common Sense Machines, Perplexity.ai, Pecan.ai, Pindrop, Spawning & others. Previously, Abhay was the CTO, CPO & EVP of Adobe, from 2015 to 2022 & was General Manager at Microsoft for a decade from 2002-2011.

Follow the Hosts and the Guest:

• Amit Prakash
  LinkedIn - https://www.linkedin.com/in/amit-prakash-50719a2/
  Twitter/X - https://x.com/amitp42
• Abhay Parasnis
  LinkedIn – https://www.linkedin.com/in/abhayparasnis/
  Twitter/X – https://x.com/parasnis

Share Your Thoughts:

Have questions, comments, or ideas for future episodes? Email us at EffortlessPodcastHQ@gmail.com

Don’t forget to Like, Comment, and Subscribe for more conversations at the intersection of AI, technology, and innovation.

What drives real product growth—launching new features, or helping existing ones land? In this episode of The Effortless Podcast, Dheeraj Pandey and Amit Prakash sit down with Ken Rudin, former Head of Growth at Google, Facebook, Zynga, and ThoughtSpot, to unpack 15 years of lessons at the intersection of analytics and product.

Ken shares the story of how a simple nudge doubled Google Search engagement, why retention curves are the truest measure of product–market fit, and how startups should think about growth before and after finding PMF. Along the way, he introduces frameworks like ARIA (Analyze, Reduce, Introduce, Assist) and MUD (Meaningful, Unique, Defensible) to help founders systematize growth instead of chasing hacks.

From cross-selling in corner-store SaaS to the surprising power of changing a Google Ads hyphen into a vertical bar, this conversation shows why growth is less about tricks and more about rigorous, creative experimentation.

00:00 – Introduction: Ken’s career journey across Zynga, Facebook, Google, and ThoughtSpot

02:00 – The Google “Sports Scores” story: Nudges that doubled engagement

08:00 – Launches vs. Landings: Why most features stall without growth focus

15:00 – When to invest in growth: Signals post-PMF and small-team leverage

22:00 – Corner-store SaaS case study: Cross-sell, pricing insights, and awareness gaps

27:00 – Counterintuitive nudges: Google Ads and the “– vs. |” experiment

32:00 – Growth as a scientific process: Hypotheses, experiments, and iteration

35:00 – Retention curves as PMF: Engagement as the strongest proxy

43:00 – Common traps: Acquisition obsession and vanity metrics

55:00 – Differentiation with MUD: Meaningful, Unique, Defensible advantages

01:03:00 – The ARIA framework: Analyze, Reduce, Introduce, Assist

01:10:00 – Fun Q&A: TED Talks, awkwardness, posture, and Peter Gabriel

Ken Rudin – Growth and analytics leader with senior roles at Google, Facebook, Zynga, and ThoughtSpot. Advisor to startups on scaling growth and building data-driven teams.

Amit Prakash – Co-founder and CTO at ThoughtSpot, former engineer at Google AdSense and Microsoft Bing.

Amit Prakash
LinkedIn – https://www.linkedin.com/in/amit-prakash-50719a2/
Twitter/X – https://x.com/amitp42

Ken Rudin

LinkedIn – https://www.linkedin.com/in/kenrudin/

Have questions, comments, or ideas for future episodes? Email us at EffortlessPodcastHQ@gmail.com

Don’t forget to Like, Comment, and Subscribe for more conversations at the intersection of growth, analytics, and innovation.