My guest today is Arvind Jain, the founder and CEO of Glean. Before Glean, Arvind spent over a decade building Google's search infrastructure. He then co-founded Rubrik, which recently passed $1B ARR.With Glean, Arvind is tackling the longstanding challenge of enterprise search. Yet his vision goes beyond this. He believes every employee should have their own team of AI agents to help them work smarter and achieve more. In our conversation, Arvind shares his journey as a technical founder and offers his unique perspective on what it takes to build a successful startup today. We also discuss where AI is heading, and where he sees the biggest opportunities for founders. Hope you find this conversation valuable! Chapters:00:00 Cold open04:42 How Arvind began his journey in search06:59 Arvind on Glean's mission08:50 The evolution of enterprise search12:56 How AI unlocks a new dimension for search16:56 Lessons for AI startup founders21:23 Navigating the AI startup landscape25:44 The "build vs. buy" decision with AI models31:09 Defining the role of AI in business34:57 The future of work with AI agents39:30 The shift from SaaS to Service-as-Software41:21 Concluding thoughts

Frank Slootman, Chairman of the Board at Snowflake, shares his groundbreaking perspective on leadership by blending passion with managerial skill. He challenges the traditional 'founder vs. manager' mindset, emphasizing the importance of intellectual honesty and the need for adaptable leadership. Frank also discusses the critical balance between empowerment and hands-on involvement, drawing insights from his experiences at Snowflake and ServiceNow. Lastly, he touches on the transformative impact of AI and the future of app ecosystems in business.

Aaron Levie, co-founder and CEO of Box, has guided the cloud content management platform from a dorm room project into a publicly traded company with over $1B in annual revenue. In his second appearance on B2BaCEO, Aaron reflects on his founder journey, sharing how Box capitalized on cloud computing and their recent push to integrate generative AI.But our conversation goes far beyond Box. Aaron’s role has given him a unique vantage point on what the latest advances in AI mean for founders. We explore the AI applications that excite him most, where he sees opportunities for startups over incumbents, and the potential areas in AI that founders might be overlooking.(0:00) Intro(2:26) The Box journey(4:23) Transitioning to enterprise(8:26) Building a GTM flywheel(11:45) Lessons from the enterprise journey(15:16) Where AI is heading(18:14) Facing the innovator's dilemma(20:54) AI agents(26:15) Why AI is positive sum for the economy(30:24) The AI doomer debate(34:22) The evolving model ecosystem(40:30) Parting advice for founders

In this episode, I talk with Srinath Sridhar, CEO & Cofounder of Regie.ai, who has always been ahead of the AI curve. Sri and his co-founder Matt Millen started Regie.ai in 2019 with the idea that GPT-3 would transform how all of us write emails. Today, Regie uses AI to automate sales prospecting for the enterprise. The company's Auto-Pilot automates most of the repetitive tasks involved in demand generation, including writing sequences, scheduling calls and responding to emails. Sri knew in early 2019 that LLMs would be a game-changer. What he didn’t know was exactly what product to build. In this episode, we’ll dig into the details of how he did it.

Mohit Aron, founder of Cohesity and Nutanix, shares startup validation frameworks, product-market fit insights, and team building lessons. He emphasizes founder honesty, market evaluation, and scaling challenges. The discussion also covers generative AI's potential impact on enterprise technology and recommendations for new CEOs.

In this conversation, Sanjit Biswas, co-founder and CEO of Samsara and former Meraki co-founder, shares his remarkable journey from leaving a Ph.D. program at MIT to building two successful startups. He discusses Meraki's pivot to enterprise sales and its acquisition by Cisco for $1.2 billion. Sanjit reveals how Samsara achieved $1 billion in ARR through customer feedback and strategic capital allocation. He also shares insights on generative AI's potential and the vital role of company culture in scaling businesses. Engaging and inspiring!

My guest today is Doug Winter, the founder and CEO of Seismic, a leading enterprise sales enablement platform. Today, Seismic has a team of 1,500 people and nearly $400 million in recurring revenue. We start the conversation with Doug explaining what sales enablement actually means. From there, we turn to the early days of Seismic and unpack Doug’s approach to finding product-market fit, positioning, and targeting enterprise customers from day one. He speaks candidly about the challenges of scaling and closes with actionable advice for founders in 2024. Fewer than 1% of B2B software companies reach Seismic’s scale. Doug’s story offers a valuable blueprint for founders with similarly audacious ambitions. I hope you find this conversation as inspiring as I did. Let’s dive in! (00:00) Cold open (2:21) Doug explains what sales enablement is (3:39) Genesis of the idea for Seismic (7:08) Seismic's scrappy early days (13:10) Lessons from fundraising (18:23) Targeting large enterprises from day one (22:32) Scaling a GTM engine (28:23) Making proactive leadership changes (37:12) Running great board meetings (40:59) Impact of AI on Seismic's business (44:42) Advice for founders starting in 2024

Naveen Rao, Co-founder of MosaicML and head of Generative AI at Databricks, shares insights on AI landscape, MosaicML acquisition, urgent AI questions, and future of generative AI. He reflects on past successes, challenges, and offers valuable lessons for founders navigating the AI moment.

Robert Nishihara, Co-Founder & CEO of Anyscale, discusses building a distributed computing system for AI, the challenges of managing deployment models, hiring and building a team, importance of repetition and learning from founding stories, and optimism for the future of technology.

My guest this month is Tracy Young, the co-founder and former CEO of PlanGrid, a productivity tool for construction companies. From going through YC and losing a co-founder to cancer, to being acquired by Autodesk for $875 million, Tracy has picked up many valuable lessons that other founders and CEOs can learn from. Our conversation unpacks these lessons, including finding (and keeping!) product-market fit, navigating startup growing pains, showing up effectively to board meetings, and managing the emotional toll of fundraising. We also speak about Tracy’s new venture, TigerEye, and what she’s doing differently the second time around. After having countless conversations with founders over the years, I thought I’d heard it all. Tracy proved me wrong. Her story serves as an inspiration for aspiring entrepreneurs in any industry.