B2BaCEO (with Ashu Garg)

My guest today is Ramesh Srinivasan, a senior partner at McKinsey and trusted advisor to some of the world’s top CEOs. Over his career, Ramesh has worked with leaders at companies like Cognizant, Moderna, Nissan, and Delta, helping them navigate tough challenges and scale high-performing teams.

Ramesh just published a new book, The Journey of Leadership, which distills lessons from thousands of hours spent alongside top executives. In our conversation, he shares practical insights for founders on how to discover their natural leadership style, why empathy is a non-negotiable leadership skill, and what it really takes to inspire people at scale.

Hope you find this conversation valuable!

Chapters: 

• 00:00:00 Cold open
• 00:01:14 Ramesh’s backstory
• 00:04:34 Things that shaped Ramesh’s leadership philosophy
• 00:05:19 The big idea behind his book: The Journey of Leadership
• 00:09:12 Building empathy: For your team, your customers, your market
• 00:11:00 Lessons from Frank D’Souza at Cognizant
• 00:14:20 Lessons from Stéphane Bancel at Moderna
• 00:17:15 Trust, vulnerability, and the power of asking for help
• 00:19:40 Finding purpose: Starting from life’s crucible moments
• 00:22:00 Renewal: How great leaders evolve over time
• 00:24:00 Common mistakes founders make on the leadership journey
• 00:26:10 Resilience: The ultimate test of a founder’s staying power
• 00:30:20 The impact of AI on leadership and organizational change
• 00:34:00 Where AI is reshaping healthcare today
• 00:36:00 Advice for AI + healthcare founders

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 open
• 04:42 How Arvind began his journey in search
• 06:59 Arvind on Glean's mission
• 08:50 The evolution of enterprise search
• 12:56 How AI unlocks a new dimension for search
• 16:56 Lessons for AI startup founders
• 21:23 Navigating the AI startup landscape
• 25:44 The "build vs. buy" decision with AI models
• 31:09 Defining the role of AI in business
• 34:57 The future of work with AI agents
• 39:30 The shift from SaaS to Service-as-Software
• 41:21 Concluding thoughts

Frank Slootman turns the 'founder mode vs. manager mode’ debate on its head. 

Frank’s track record in B2B land is iconic: He took Data Domain from pre-revenues to a $2.5B acquisition by EMC. He led the IPO at ServiceNow, and when he left the company, it was worth $34B. Frank then took Snowflake public, and the company was worth over $70B when he retired earlier this year. 

After three successful CEO stints, Frank isn’t buying Silicon Valley’s fairytales about founders. His leadership style combines a manager’s prowess with a founder’s passion. Frank epitomizes what some might call “owner mode!”

 

(00:07) Frank's thoughts on 'founder mode' vs. 'manager mode' 

(00:47) The role of non-founder managers and CEOs 

(09:59) How to manage effectively without micro-managing 

(17:11) The importance of intellectual honesty (18:32) Frank's thoughts on being 'in the arena' 

(21:04) What it really takes to build a viable business 

(28:34) Contrasting ServiceNow and Snowflake 

(33:40) The impact of AI on business 

(39:01) The future of app ecosystems 

(44:50) Becoming a student of leadership 

(46:31) Managing investor relationships 

(48:04) Why Frank doesn't think about his legacy 

(50:17) Closing Thoughts

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.

In this episode, I'm excited to welcome Mohit Aron back to B2BaCEO for the second time. As the founder of Cohesity and co-founder of Nutanix, Mohit is a titan in the world of enterprise GTM and infrastructure software. With two wildly successful companies under his belt, he's a true expert when it comes to building enterprise software businesses from the ground up. In our conversation, Mohit shares his proven frameworks for validating startup ideas. He reveals hard-won lessons from starting Nutanix and Cohesity, with real-world examples that bring his advice to life. We explore product-market fit—what it really looks like in practice—as well as how to build a team and manage performance in a high-growth startup. We wrap up by discussing the topic du jour, generative AI, and the opportunities it opens for startups. This episode is full of insights for technical founders. I hope you enjoy it! (00:00) Intro (00:21) Mohit's framework for a bulletproof startup hypothesis document (07:53) Why your MVP shouldn't be your full vision (10:39) Cohesity's journey from 0 to 1, 1 to 10, and 10 to 100+ (17:19) Examples of founders not being intellectually honest about their hypotheses (20:35) How to accurately size your startup's market (TAM) (23:55) Balancing founder conviction with naysayer feedback (31:02) Adapting the hypothesis document for the generative AI era (34:19) Mohit's definition of product-market fit (39:05) When to hit the gas on sales hiring (and when not to) (44:59) Mohit's system for competency-based hiring (53:17) Implementing performance management via quarterly calibrations (56:00) What Mohit would do differently as a technical founder (58:07) Mohit's top advice for founders (60:09) The industries ripe for disruption by generative AI (62:04) Book recommendations for founders

My guest today is Sanjit Biswas, the co-founder and CEO of Samsara, a platform that helps companies digitize their physical operations. In 2023, Samsara reached $1 billion in ARR, making it one of the fastest startups in history to hit this milestone. 

But this wasn't Sanjit's first major success. Before starting Samsara, Sanjit left his Ph.D at MIT to build Meraki, a cloud networking company that Cisco acquired for $1.2 billion in 2012.

In our conversation, Sanjit shares his journey from grad school research to bootstrapping Meraki in the early days. He reflects on the lessons he learned from Meraki's pivot to the enterprise, the decision to sell to Cisco, and the insights that led him to start Samsara. 

We then turn to how Samsara found product-market fit, Sanjit's philosophy on allocating capital, and the areas where he believes generative AI will have the biggest impact. 

It was a really fun and insightful conversation that I think you'll enjoy!

(00:00) Intro
(00:16) Sanjit's background and the genesis of Meraki
(06:25) Meraki's pivot to the enterprise and rapid growth
(09:45) Lessons from building Meraki's enterprise sales motion
(16:15) The decision to sell Meraki to Cisco
(20:05) Founding Samsara and its mission
(27:11) Defining Samsara's product strategy based on customer feedback
(31:00) Samsara's unique journey to $1B in revenue
(39:16) Sanjit’s "70/20/10” framework for allocating capital
(43:13) The importance of board alignment and company culture
(50:58) Sanjit's thoughts on AI and hype cycles
(54:22) Sanjit's advice for aspiring entrepreneurs

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

My guest this month is Naveen Rao, the co-founder of MosaicML and current head of Generative AI at Databricks. Naveen's journey is unique, as it echoes the evolution of AI itself. He’s best known for founding and selling two successful companies. The first, Nervana, an AI-focused chip company, was acquired by Intel for $400 million in 2016. The second, MosaicML, was acquired by Databricks in June for $1.3 billion. In our conversation, we unpack the insights and frameworks that led Naveen to make these bets in the first place. We begin by exploring his long history in AI research and startups, from his early days at Qualcomm, his founding of Nervana, and the genesis of MosaicML. We then turn to the complexities of the ever-changing AI landscape and go behind the scenes of MosaicML’s acquisition by Databricks. We close with Naveen’s takes on the most urgent questions in AI, including the recent tumult at OpenAI, the road to AGI, the role of regulation, and where he thinks generative AI will go next. What struck me most is Naveen’s remarkable ability to not only anticipate the future but also actively pave the path toward it. For founders looking to navigate our current AI moment, this episode is full of valuable lessons.