The Founder to Fortune Podcast

Title: Is the CTO Irrelevant for Early-Stage Startups?

Episode Summary: In an era where generative AI can write code instantly and stand up software out of the box, what is the actual role of a technical co-founder? In this episode, we sit down with Vlad Pick, former technical co-founder of Tone Messaging and current Engineering Manager at Attentive, to unpack the massive existential shift happening in startup leadership.

Vlad pulls back the curtain on how he navigated a high-stakes enterprise acquisition, why he believes pure "code-writing" engineers have an immediate expiration date, and why the...

The “traditional” engineering org chart is a relic of a time when code was the primary bottleneck. For technical founders today, the challenge has shifted from managing human velocity to orchestrating agentic systems and defending product taste.

In a recent Founder to Fortune conversation, Clayton Kim, CTO of FlyKitt and professional aerial acrobat, broke down how he transitioned from managing dozens at Wayfair to running a “wizard-led” team of three that outpaces traditional squads.

The Death of the Middle Manager

Clayton’s thesis is clear: the industry is over-correcting toward a flattened organization. The “middl...

DevTool Founder-mode: Hiring for Grit, Reading Code, and Building Trust

Guest: Ajay Tripathy, Former CTO of Stackwatch (exit: IBM)

Episode Summary: Is the era of the "coder" coming to an end? Former Kubecost CTO Ajay Tripathy joins the show to discuss why the next generation of founders must pivot from writing code to owning business outcomes. We explore his "grit-first" hiring filter, how to engineer for business outcomes, ideal co-founder relationship and so much more.

Timestamps:

[01:01] – The Google Origins: Life inside the Borg project and the "Life is Short" catalyst for le...

Episode: Engineering Capital: Investing in Technical Risk

Guest: Ashmeet Sidana (Engineering Capital)

Host: Vidya Raman — Founder to Fortune

Episode overview

In this episode, Ashmeet Sidana breaks down what it means to invest in technical risk—the “can this even be built?” kind—and why it creates leverage when founders get it right. We talk about what he looks for in first meetings, how to avoid PMF “progress theater,” why founders must learn sales, and what early-career investors can do to be genuinely valuable.

Key takeaways

Technical...

Conflict between co-founders is inevitable.

Letting it spiral out of control is optional.

In this episode of Founder to Fortune, Vidya Raman sits down with Dr. Matt Jones — licensed psychologist, co-founder coach, and author of The Co-Founder Effect — to explore why the co-founder relationship is the single most under-managed risk in startups .

Matt works exclusively with founding teams to improve communication, teamwork, and decision-making. In this conversation, he shares both deep psychological insight and highly tactical tools founders can implement immediately.

Key Topics Covered

• Why the co-founder relationship is the floo...

Most first-time founders believe startups fail because of bad ideas, weak technology, or poor timing.

In this episode, Tarang Vaish argues that the real failure mode is far less obvious—and far more dangerous: people risk.

Drawing from his journey across hardware, data infrastructure, SaaS, and AI, Tarang shares hard-earned lessons on co-founder dynamics, solo founding, risk stacking, and founder mindset. He also offers a practical mental model for using AI effectively—by treating it like an intern, not magic.

This conversation is for founders who want to think more clearly about risk, lead...

Episode Summary

Most AI conversations start with parameter counts. This one doesn’t.

In this episode, we go inside the origin story of smallest.ai, a company built on the contrarian belief that true intelligence can be achieved with compute-constrained, smaller models — especially when the goal is real-time speech intelligence that can run actual workflows in production. 

Sudarshan shares how his background in self-driving vehicles shaped his thinking on reliability, active learning loops, and why 90–95% of the work lives in data and labeling, not model training. We then zoom into real-world enterpr...

What if your biggest partnership was actually holding you back?

Pankaj Dugar, who helped scale Databricks and drove strategy at AI21 Labs, joins Vidya Raman to share why partnerships fail right after the Press Release — and how to build ones that actually sell.

This episode breaks down the uncomfortable truths behind partner ecosystems, the role of technical integration, and why “boring is where the money is.”

If you’ve ever thought a partnership could change your startup’s trajectory — listen before you celebrate.

What happens when PMs, designers, and AI all start speaking the same language?

In this episode, Vidya Raman sits down with Hailey Nevins (Director of UX Foundations at MongoDB) and Wenbo Wang (founding designer and former Databricks/Cloudera product designer) to explore how vibe coding is collapsing the old boundaries between design, product, and engineering.

You’ll hear how GenAI is forcing UX to evolve—from pixel pushing to taste-driven orchestration—and why the best design teams now operate at startup speed without sacrificing rigor.

We go deep into:

* How “vibe coding”...

In this engaging conversation, Kady Srinivasan, CMO of You.com shares her journey from software engineering to becoming a marketing leader across various industries. She discusses the importance of defining an Ideal Customer Profile (ICP) in B2B marketing, the impact of AI on marketing strategies, and the evolving role of marketers in a fast-paced environment. Kady emphasizes the need for discipline in narrowing down ICP, the significance of content creation, and the necessity of hiring the right marketing talent. She also highlights the importance of judgment in marketing and the need for continuous learning in the ever-changing landscape...

Ely Kahn’s career spans government, startups, and now leading product at SentinelOne. From shaping U.S. cybersecurity strategy at the White House to building one of AWS’s early security products to launching SentinelOne’s fastest-growing AI product line, his journey offers a rare vantage point on how security and product innovation intersect.

In this episode, we dig into:

* How AI is transforming threat hunting and investigations—and what that really means for teams on the ground.

* The surprising role of “digital twins” in scaling product management.

* Why cybersecurity, despite the noise an...

* Veteran GTM leader Jim Fisher shares lessons from scaling Cloudera from $50M to $1B ARR and advising today’s fastest-growing startups.

* The three golden KPIs that reveal the health of any go-to-market strategy.

* Why most founders get ICP wrong—and how to fix it.

* The surprising truth: consistency, not revenue, is the real signal your GTM is working.

* When to hire a GTM advisor, fractional leader, or full-time VP—and how to know the right timing.

* How AI is reshaping sales with coaching, opportunity analysis, and bias-free deal reviews.

...

In this episode with Saket Modi, we explore:

* How a college dorm-room hacker turned an idea into a global cybersecurity company

* The surprising way he landed his first customers (hint: it involved live hacks)

* Why he once turned down a multimillion-dollar deal—and why it was the best decision

* His unconventional approach to learning (including hiring a PhD tutor just for himself)

* The leadership principle he lives by: never ask your team to do what you won’t

* Why SAFE is betting on Cyber AGI—and what that m...

What happens when a veteran CTO jumps into the world of AI-native tools, no-code platforms, and “vibe coding”? In this episode, Michael Raybman—former Hustle Fund CTO and founder whisperer—joins Vidya to break down how building software has been turned on its head.

They explore:

* Why non-technical founders can go further, faster than ever before

* The tools that actually deliver (with a live build of a working app in minutes!)

* When to go from solo tinkering to hiring real developers

* How to spot and fix a broken engineering team

What happens when two long-time product and engineering leaders—who once yelled at each other across the office—reunite on a podcast to decode the future of data and AI?

In this episode, Vidya Raman hosts Anjan Kundavaram (CPO at Fivetran) and Chandler Hoisington (formerly CPO at EnterpriseDB and AWS exec) for a candid, behind-the-scenes conversation that spans:

* Why the Lakehouse architecture is more than a buzzword—and how Iceberg is quietly winning the open standards race

* Whether RAG, embeddings, and vector databases are already becoming yesterday’s news

* What’s really hol...

What happens when one of the world’s largest asset managers decides to think like a tech company? In this episode, Diwakar Goel, Global Head of Data at BlackRock, pulls back the curtain on how his team is orchestrating one of the most ambitious data transformations in the financial world.

From powering global investments with a touchless analytics “green package,” to reimagining operations through a homegrown AI-infused task platform, Diwakar shares how data governance, privacy, and automation are embedded not as afterthoughts—but as design principles. You’ll hear how they balance speed and regulation, why operational excellence...

In this episode, we go inside the minds of two powerhouse CISOs—Rinki Sethi (Upwind, ex-Twitter, Rubrik, Bill.com) and Lucas Moody (Alteryx, ex-Palo Alto Networks)—as they unpack what it really takes to secure an enterprise in today’s world of AI, multi-cloud sprawl, and constant threat exposure.

They talk candidly about:

* The evolving role of the CISO—from reactive firewalls to boardroom influence

* Why some vendors gain trust while others get ignored

* The hidden complexity behind “simple” security practices like IAM

* What early-stage founders consistently get wrong—and how to fix...

In this must-listen episode of The Enterprise GTM Podcast, Pavi Ramamurthy, Global CIO and CSO of Blackhawk Network, shares a candid and deeply insightful look into the world of enterprise security, tech innovation, and risk management. From managing massive fraud prevention systems behind the gift cards you see at Target, to navigating startup pitches and the realities of AI adoption—this is a masterclass in modern IT and security leadership.

💡 What You’ll Learn:

• How Pavi balances business priorities vs. security risks

• Why startup founders need to drop the pitch and start a rea...

In this episode, Diamond Bishop shares his fascinating journey through AI, machine learning, and enterprise software, from working at Microsoft (Cortana), Amazon (Alexa), AWS, and Meta (PyTorch) to founding Augmend, an AI-driven DevOps knowledge assistant, which Datadog later acquired.

He dives deep into building AI-powered enterprise products, the challenges of selling into large organizations, and why AI-driven automation is the future of DevOps and security operations. Diamond also unveils Bits.ai, Datadog’s intelligent AI assistant designed to automate on-call incident resolution, debugging, and code error fixing.

For founders, product leaders, and AI enthusiasts, this ep...

Imagine walking into a digital store where the AI knows exactly what you want before you do. No more endless scrolling. No more generic recommendations. Just hyper-personalized shopping at lightning speed.

In this electrifying episode of The Enterprise GTM Podcast, Vidya Raman sits down with two AI powerhouses:

🔹 Sameer Singh, CTO of Spiffy, a startup rethinking AI-powered shopping assistants

🔹 Anu Trivedi, Head of R&D at Flipkart, India’s largest e-commerce marketplace

Together, they pull back the curtain on the AI revolution that’s already reshaping how we buy, sell, and engage wit...

In this must-listen episode of the Enterprise GTM Podcast, I dive deep with two powerhouse AI experts:

🎙 Manasi Vartak (Chief AI Architect at Cloudera)

🎙 Shreya Shankar (PhD Candidate, UC Berkeley)

We discuss the current landscape of GenAI in enterprises. We explore the challenges of productionizing AI applications, the importance of data privacy, and the evolving use cases within large organizations. Manasi shares insights from her experience at Cloudera, highlighting the slow adoption of GenAI in production and the prevalent use of internal applications. Shreya elaborates on her research at UC Berkeley, including how her wo...

In today's episode, we sit down with Jerry Ting to delve into his experience of founding and scaling a startup in the world of AI-powered contract management. Jerry is the Founder and CEO of Evisort, a cutting-edge AI-powered contract management platform transforming how organizations manage, analyze, and automate their legal documents. Jerry's vision has been instrumental in establishing Evisort as an innovator at the intersection of law and technology.

In our conversation, we discuss Jerry’s transition from sales to law, the early days of Evisort, and how he overcame skepticism to secure the company’s first clie...

Welcome back to another episode of The Enterprise GTM Podcast. Today we are joined by the Vice President of Enterprise Data and Analytics at Swire Coca-Cola, Bharathi Rajan.

In this episode, Bharathi delves into crucial aspects of GTM that founders should pay attention to:

🔹 Know Your Customers and Their KPIs: Understanding what drives your customers is key to offering solutions that truly meet their needs.

🔹 Transferable KPIs Across Industries: Bharathi shares how fundamental business problems remain consistent across sectors like healthcare, finance, and manufacturing. Founders should leverage this when pitching horizontal products to differ...

Founder-led sales are common in early-stage startups. But, they could be much more effective with a deeper understanding of sales fundamentals. Joining us today is Leslie Venetz, founder of The Sales-Led GTM Agency to discuss how founders can level up their skills and transform their sales. Drawing on her extensive history in B2B sales, which includes over 250,000 cold calls, Leslie covers everything founders need to know, from earning the right to your prospect’s attention to efficiently managing your time during the sales process. She shares her top tips on crafting concise, value-driven emails, how to use AI in...

Barry Dauber is the VP of Sales and Business Development at MosaicML (recently acquired by Databricks) which is centered on making generative AI easy to use and widely accessible. Today, Barry joins us to discuss the role of sales, marketing, and business development in early-stage startups with a specific emphasis on MosaicML. 

Key Points From This Episode: 

* Barry Dauber walks us through the evolution of MosaicML's core offering. 

* His thoughts on sales and in particular, how to know when it's time to scale. 

* Barry's protocol for when the scaling plan...

In this episode, three-time tech company founder Chet Kapoor joins us to offer his insights on finding the right tech waves to ride and timing them well. Chet shares the principles that underpin his professional identity and decision-making process and highlights the importance of creating and maintaining momentum. Chet provides some timeless advice on how to approach enterprise sales for developer tools, the right kinds of partnerships to prioritize, his outlook on competition, and so much more. He also answers a number of rapid-fire questions that reveal his predictions for the future of data infrastructure, LLMs, data engineering, and...

Developer-facing startups drive software innovation, crafting tools tailored for developers' needs, but how do they differ from traditional startups? In this episode, we sit down with Adam Frankl to unpack the nuances of startups focusing on the development tool space. Adam Frankl is a seasoned marketing strategist focused on empowering startup founders in the tech industry. With a rich background as the first VP of Marketing at three developer-facing unicorns—JFrog, Neo4j, and Sourcegraph—Adam brings a wealth of experience to the table. He is also writing a book called The Developer Facing Startup which focuses on helping lead...

In this episode, we discuss what it means to build a business based on open source for infra and dev tool founders. Sharing her broad and deep insights with us is Emily Omier, the world’s leading expert in positioning OSS companies for success.

Key Points From This Episode:

* The Perennial and fundamental challenge for an OSS company is building a business while still having an OSS project that delivers clear value in and of itself and is entirely free to the world!

* Understand the difference between project-market fit and product-market fi...

Now that AI has been fully integrated into our lives, the question among developers, engineers, and even end-users is no longer “What is AI?” but rather “How can I use AI in the best possible way?” We are joined today by Sushant Hiray, the Senior Director of Machine Learning at the business communications platform, RingCentral, and Guhan Venguswamy, the Head of Platform at Jasper – a marketing-focused AI copilot. The pair are here to discuss how their companies have adapted to the explosion of LLMs, beginning with what their businesses are all about, the products they offer, and the customers they aim t...

Ajeet Singh is the founder of not one but two unicorns– Ajeet founded Nutanix in 2009 which went public in 2016 and was the largest tech IPO of that year. It is today a public company making well over 1B in ARR and has more than 23K+ customers worldwide. Nutanix is a leader in the hyper-converged infrastructure space. Ajeet also founded Thoughtspot in 2012 which is valued at over 4B+. Thoughtspot is in the Business Intelligence space, taking on incumbents such as Tableau, Microsoft PowerBI, and many others.

Topics we discuss:

* How should founders think about ri...

Welcome back to The Enterprise GTM Podcast! Today, we are joined by the CEO of Armorblox, DJ Sampath. Armorblox was a cybersecurity startup that built the world’s first natural language understanding platform to intelligently detect, alert, and protect identity-related attacks and data loss.

DJ is the quintessential engineer turned CEO. He has a PhD in computer engineering and started his career as a software engineer before starting Armorbox.

Tuning in, you’ll hear about his startup journey, the most challenging part of being a CEO, why everyone can sell, how he knows when a prod...

With the release of ChatGPT, AI has caught everyone’s attention and we are seeing it in more and more consumer and enterprise products. As leaders in the field of AI who have been working with AI before it became a rage, we have some of the best minds to share advice to founders who are building products using AI.

Our guests today include:

* Saurabh the VP of engineering at Uniphore, which is a leading conversational AI company. Saurabh shares his experience building emotion AI, which is an industry-leading multi-modal AI model that he...

In this fascinating episode, we embark on a captivating journey into the intricate realm of developer relations and advocacy. Our esteemed guests, Nadine Farah, the illustrious Head of Developer Relations at Onehouse, and Tao Hansen, the visionary Head of Developer Relations at Garden, serve as our trusted guides through this essential topic. Nadine, a distinguished Apache Hudi contributor, is renowned for her dedication to forging connections between engineering prowess, product innovation, and strategic marketing, all in the pursuit of propelling product adoption. Tao Hansen, a former luminary in the world of short film, is passionate about connecting people and...

Are developers impossible to market to? Micheline Nijmeh is the Chief Marketing Officer at JFrog, and she joins us to suggest otherwise. Beginning with an overview of the varied roles in sales and marketing that led her to the expertise she has today, Micheline shares her perspective on getting to know your users, defining your personas, and tailoring your marketing to different audiences. We explore growing the impact you make from team-focused to reaching budget owners and Micheline offers guidance on how to become a part of the community rather than approaching it from the outside. Our conversation touches...