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 real conversation

• The surprising cost of switching vendors—even if the tech is “10x better”

• Why shadow AI isn’t so different from shadow IT—and how to manage both

• The power of CISO communities and peer recommendations

• Why “best-of-suite” often wins over “best-of-breed” in today’s enterprise deals

• What makes a new security vendor stand out—or get silently passed over

• The magic wand wish that Pavi has from startups

💬 Memorable Quote:

“I ask one question before investing in any solution: What’s the cost of not doing this?”

“Know your CISO!”

👀 Who Should Listen:

• Founders and startups pitching to the enterprise market

• Security and IT professionals navigating risk and innovation

• Anyone curious about how real enterprise decisions get made

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 episode is packed with lessons on enterprise GTM (Go-To-Market) for Developer Tools, AI-driven automation, and the future of software engineering.

Key Topics Discussed:

1️⃣ The Evolution of AI & Machine Learning

2️⃣ Founding Augmend: AI for DevOps Knowledge Sharing

3️⃣ The biggest challenges for Dev Tool startups

4️⃣ Bits.ai: The AI Assistant for DevOps & Security

5️⃣ Lessons in building with Gen AI & GTM Insights

Who Should Listen?

✅ AI/ML Engineers & DevOps Professionals – Learn how AI-driven automation is transforming workflows

✅ Tech Founders & Enterprise GTM Leaders – Get real-world insights on selling AI to enterprises

✅ Investors & AI Enthusiasts – Understand the next wave of AI-powered enterprise automation

Resources & Links:

🔗 Follow Diamond Bishop on LinkedIn

🔗 Datadog Bits.ai (Private Beta)

📢 Enjoyed this episode? Don’t forget to subscribe, rate, and share! 🚀

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 with products online.

What’s Inside?

❓ Why are today’s product recommendations so outdated—and how is AI fixing it?

🤯 Are personalized AI shopping assistants finally here? And are they actually good?

🚀 How is Flipkart handling AI at a mind-blowing scale of 600M+ customers?

🔥 Is AI-powered e-commerce too smart—or not smart enough?

If you’re curious about how AI will change the way we shop forever, this is an episode you can’t afford to miss!

Links mentioned in today’s episode:

Sameer Singh

Spiffy AI

Anu Trivedi

Flipkart

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 work could transform data engineering.

The conversation emphasizes the need for new tools and strategies to navigate the complexities of AI deployment and the significance of benchmarking in this evolving field. This conversation explores the evolving landscape of data engineering and the role of Generative AI (Gen.AI) in automating processes, simplifying data management, and enhancing user experience.

The speakers discuss the importance of coding assistants, the need for new benchmarks in AI tools, and the critical role of user experience in designing AI applications. They emphasize the necessity of education and training to help users effectively leverage AI technologies in their workflows.

Takeaways

* The excitement about GenAI remains strong in enterprises.

* Adoption of GenAI in production is still under 10%.

* Internal use cases dominate the current landscape of GenAI applications.

* The RAG pattern is a leading use case for enterprises.

* Data privacy and security are major concerns for enterprises.

* AI is becoming more democratized, allowing non-experts to build applications.

* Productionizing AI requires significant effort and infrastructure.

* Shreya's research focuses on optimizing database interactions with GenAI.

* Accuracy in prompting is a complex and fuzzy concept.

* Benchmarking in GenAI is challenging due to the lack of ground truth. The future of data engineering will involve more automation and less manual toil.

* Gen.AI can simplify data management tasks significantly.

* Natural language processing will make data access easier for non-technical users.

* User experience is crucial for the success of AI applications.

* AI tools should be designed for seamless human-AI collaboration.

* Benchmarks for AI tools need to be redefined beyond traditional accuracy measures.

* Education is key to helping users effectively utilize AI technologies.

* Domain experts will benefit from tailored coding assistants in their specific environments.

* The transition from creation to review in AI applications is essential for user engagement.

* Accessibility of Gen.AI presents new opportunities for education and innovation.

Chapters

00:00 Introduction to AI Experts

02:05 Current State of GenAI in Enterprises

05:58 Use Cases and Adoption Challenges

11:59 Parallels in AI Evolution

16:02 Shreya's Research on GenAI and Databases

22:41 The Future of Data Engineering and Automation

24:11 Simplifying Data Management with Gen.AI

27:20 The Role of Coding Assistants in Data Tasks

30:47 Rethinking Benchmarks for AI Tools

35:33 User Experience in AI Applications

39:20 Designing for Human-AI Collaboration

44:18 Education and Training for Effective AI Use

Links mentioned in today’s episode:

Shreya Shankar

Shreya’s work DocETL

Manasi Vartak on Linkedin

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 clients. We also unpack the steps to identifying the right time to build sales and marketing teams, determining pricing, and the importance of a customer-first approach. Explore Evisort’s mission-driven innovation approach, the strategy of “land and expand,” and the advantages startups have over larger competitors in delivering user-focused solutions. Join us for a detailed look at the challenges and successes of building a transformative legal tech company from the ground up with Jerry Ting.

Key Points From This Episode: 

* Introducing Jerry and his background in law and journey into entrepreneurship.

* Jerry explains Evisort's product-led approach to its enterprise selling motion.

* Why working with large enterprises is sometimes a curse for smaller companies.

* Making the first Sales hire for Evisort and what he would do differently.

* Discover how he determined Evisort's initial offerings and associated pricing.

* How Evisort's mission to make peoples' lives easier catalyzed its growth. 

* How do you go from departmental sales to enterprise sales.

* Jerry shares advice for budding founders of AI-native companies.

Quotes:

“[Evisort] really early on took a product-led approach in our enterprise selling motion.” — Jerry Ting [0:06:45]

“My advice to the founders listening out there is that sometimes it is a curse to actually get big enterprises [interested] in the beginning.” — Jerry Ting [0:07:55]

“If you really focus around the customer from a 360 [degree] company perspective, how you sell, how you support, how do you build your product, over time they become a great sounding board for the company strategy.” — Jerry Ting [0:18:18]

Links Mentioned in Today’s Episode:

Jerry Ting on LinkedIn

Evisort

Tim Zonca on LinkedIn

Tim Zonca on X

Vidya Raman on LinkedIn

Vidya Raman on X

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 different industry verticals.

We also dive deep into her recent product buying experience:

🔸 Continuous Engagement: Stay in your customers' inboxes and minds. Be present when you become highly relevant to them.

🔸 Power of Reference Selling: Never underestimate the influence of your current customers. Their endorsements can be game-changers.

🔸 Competitive Landscape: A good market always has competition. Learn how Bharathi's team evaluates competitors—not just on price.

🔸 Pricing, TCO, and ROI: Understand how enterprises weigh the decision between replacing existing products and adopting new ones.

One standout takeaway: Bharathi refers to the vendor they chose as a "partner." This reinforces a recurring theme we've heard throughout our podcast series, especially in conversations with Leslie Venetz. Customers today are seeking partners, not just products or platforms.

👉 If you're keen to gain invaluable insights from the other side of the table, this episode is a must-listen!

Quotes:

“Data is so foundational for us to do anything in the AI – space.” — Bharathi Rajan [0:04:46]

“For me, our customers are everyone across the organization.” — Bharathi Rajan [0:08:00]

“Data is data at the end of the day.” — Bharathi Rajan [0:08:40]

“Deeply understanding your customer’s business will make a big difference even in your first dialog with a prospect.”— Bharathi Rajan [0:14:00]

Links Mentioned in Today’s Episode:

Bharathi Rajan on LinkedIn

Swire Coca-ColaTim Zonca on LinkedIn

Tim Zonca on X

Vidya Raman on LinkedIn

Vidya Raman on X

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 sales without over-relying on it, and how to strategically time your demos. Leslie also shares her unique perspective on objections, including how to figure out which objections are worth addressing, and why you should always lead with curiosity.

Key Points From This Episode: 

* Some background on Leslie Venetz and her extensive background in sales.

* Improving founder-led sales, especially in early-stage startups.

* The key to developing active listening skills and why it is essential in sales.

* Cold emails: best practices and common mistakes.

* Key components of highly relevant messaging and how to audit your emails.

* What your initial email outreach should look like.

* Why you need to earn the right to write longer emails.

* Leslie’s advice on how to use AI in sales – and how not to use it.

* The importance of personalized outreach in the age of AI.

* How to strategically time your product demos in a prospective customer call.

* Recognizing different types of objections and how to address them.

* Utilizing events as part of a multi-channel marketing approach.

* Leslie answers our rapid-fire questions on AI, cold-calling, and more!

Quotes:

“Founder-led sales, which is usually the norm for early-stage startups, can be so much more effective if only founders could better understand some of the foundational aspects of sales.” — @veenormous [0:04:17]

“It is your responsibility to earn the right to your prospect's time” — @LeslieVenetz [0:11:41]

“We want to do everything that we can to reduce the cognitive load – and make it easy for them to scan and digest that email.” — @LeslieVenetz [0:15:16]

“Especially for early-stage founders. You all are busy. – You do not have the time to spend an hour sending an email to a prospect that doesn't actually want you to email them.” — @LeslieVenetz [0:34:05]

Links Mentioned in Today’s Episode:

Leslie Venetz

Leslie Venetz on LinkedInJill Konrath

Snap Selling

Tim Zonca on LinkedIn

Tim Zonca on X

Vidya Raman on LinkedIn

Vidya Raman on X

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 includes bringing in new partners.

* How to stay in your lane as a startup with great ambitions, and why this matters. 

* Our guest unpacks the differences and similarities between market adoption of big data and generative AI. 

* The major roadblocks that slow and prevent the evolution of ML and GenAI.

Quotes:

“As we learn in sales, especially in the startup world, 'no' is almost as exciting as ‘yes.’” — @barrydauber [0:15:07]

“The easiest way to drive a partnership, especially as the small company, is you need to bring a customer.” — @barrydauber [0:19:27]

“If an early-stage startup positions themselves as a platform, it would be disqualified by enterprises” — @barrydauber [0:23:31]

“Gen AI SaaS will win over DIY efforts in large enterprises.” — @barrydauber [0:42:32]

“Business users will be the primary users of ML/AI tools 5 years from now.” — @barrydauber [0:48:38]

Links Mentioned in Today’s Episode:

Barry Dauber on LinkedIn 

Barry Dauber on X

MosaicML 

Databricks 

Tim Zonca on LinkedIn

Tim Zonca on X

Vidya Raman on LinkedIn

Vidya Raman on X

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 more!

Key Points From This Episode: 

* Introducing Chet Kapoor and his experience launching three tech companies. 

* Experiences that have defined his professional identity, from growing up in Calcutta to working alongside Steve Jobs.

* The two key principles that inform all of Chet’s decisions.

* Why momentum is so important in startups. 

* A simple yet powerful framework to create a large company.

* Datastax’s place in the current AI landscape and what it aims to do. 

* Why Chet looks most forward to transformative use cases. 

* Advice for approaching enterprise sales.

* Two ways that Chet classifies partnerships. 

* Applying caution to partner relationships.

* Chet's evolving relationship with competition. 

* The importance of leaning into your uniqueness and modifying your approach as needed.

* Predictions for how data infrastructure will change in the next five years. 

* Why he believes that LLM agent-based applications are geared to reinvent most of the enterprise software landscape as we know it. 

* Perspectives on which players stand to gain the most with the development of AI. 

* Whether or not the demand for data scientists and engineers is going to increase. 

Links Mentioned in Today’s Episode:

Chet Kapoor on LinkedIn

Chet Kapoor on X

Datastax

Tim Zonca on LinkedIn

Tim Zonca on X

Vidya Raman on LinkedIn

Vidya Raman on X

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com

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 leaders of start-ups navigate the developer landscape. In our conversation, we unpack why understanding the mindset of developers is crucial to adoption, why developers are highly skeptical of marketing, and the concept of social proof. Discover the common pitfalls marketing executives make when working with developers, why timing in marketing is crucial, and the nuances of selling the solution. Explore why founders should be posting on social media every day, the advantages that startups have, steps for shifting from a point solution to a platform solution, his alternative to the traditional marketing funnel, and more! Tune in and learn the basics of founder-led marketing with Adam Frankl!

Key Points From This Episode:

* Background about Adam and details about his upcoming book.

* How developers differ from the traditional technologist in the B2B space.

* Learn about the fundamentals that make developer tool startups unique.

* He unpacks the myth that developers hate marketing.

* Hear how founders should approach working with marketing and developers.

* Steps for identifying the best time to enter the market.

* Adam explains his idea of selling the category rather than the solution.

* When founders should consider implementing marketing strategies.

* What kind of experience is needed for a marketer to work in B2D.

* Compare platform and point solutions for applications.

* Ways the marketing funnel does not apply to dev tool startups.

* Common evaluation pitfalls founders make and how to avoid them.

* Memberships as a way to foster and grow a community.

* We end with Adam answering our set of rapid-fire questions.

Quotes:

“Developers don’t lie to other developers.” — Adam Frankl [6:00]

“Every company needs to have a technical advisory board.” — Adam Frankl [13:47]

“You are not going to be successful by being clever in a conference room. – You are going to be successful when you talk to large numbers of developers.” — Adam Frankl [13:57]

“Marketing is having a point of view and expressing it in a way that people can interact with it, engage with it, and follow you. Social media is a great gift.” — Adam Frankl [21:34]

“Developer curiosity destroys most of the [marketing funnel] metrics because developers are always discovering and researching.” — Adam Frankl [31:40]

Links Mentioned in Today’s Episode:

Adam Frankl on LinkedIn

JFrog

Neo4j

Sourcegraph

GitLab

The Art of Community

Unfair Mindshare

Tim Zonca on LinkedIn

Tim Zonca on X

Vidya Raman on LinkedIn

Vidya Raman on X

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com