Entrepreneurs often ask: When do I know it’s time to scale? Or, how do I lead when I wasn’t the original founder?

In this week’s Founded & Funded, Madrona Partner Chris Picardo sits down with Eleanor Lightbody, CEO of Luminance, who shares how she took a promising AI product and built a company culture, go-to-market motion, and product strategy that’s scaled 6x in just two years. Eleanor’s candor and tactical insights on hiring, selling, and navigating founder dynamics make this a must-listen.

Transcript: https://www.madrona.com/building-ai-that-sells-scaling-smarter-with-luminance-ceo-eleanor-lightbody/

Chapters: (00:00) Introduction (01:29) Eleanor's Career Journey (03:22) Joining Luminance and Initial Challenges (05:46) Navigating CEO Role and Company Dynamics (11:01) Transforming Luminance's Growth Trajectory (19:03) Balancing Innovation and Core Product Delivery (24:42) Building a Collaborative Culture (28:44) Challenges and Rewards of Scaling a Company (34:57) Future of AI

Most startups bolt AI onto old products.  ⁨@ravennahq⁩  reimagined the entire workflow. 

When we first met Kevin Coleman and Taylor Halliday, it was clear they weren’t just chasing the hype cycle. They were pairing AI-native architecture with deep founder-market fit, and rebuilding how internal ops work — from first principles.

Their new company, Ravenna, is going after a $160B+ market dominated by legacy players. But instead of being intimidated by incumbents, they got focused, making some smart moves that more early-stage teams should consider:

1) Speak with 30+ customers before writing a line of code 2) Define a clear ICP and pain points 3) Build natively for Slack — where support actually happens 4) Prioritize automation, iteration, and real workflow transformation 5) Stayed radically transparent with investors and early customers

At Madrona, we love backing teams that combine ambition with discipline — and Kevin and Taylor are doing just that. In this episode of Founded & Funded, they sit down with Madrona Managing Director Tim Porter and talk through their journey, what they’d do differently the second time around, and how they’re building a durable, agentic platform for internal support.

If you're a founder building in AI, SaaS, or ops — this conversation is full of lessons worth hearing.

Transcript: https://bit.ly/4ju2Cml

Chapters:  (00:00) Introduction (00:23) Meet the Founders: Taylor Halliday and Kevin Coleman (02:05) The Birth of Ravenna: Identifying the Problem (03:05) The Concept of Enterprise Service Management (04:02) The Journey from Idea to Execution (04:31) Customer Insights and Market Fit (06:42) Building a Next-Generation Platform (10:43) Slack Integration and AI Automation (14:37) Partnering with Slack: A Strategic Move (17:13) Leveraging Slack for Knowledge Management (20:13) Balancing Focus and Vision (21:07) Discovering ITSM: A Hidden Market (21:40) Expanding Beyond IT: The Universal Help Desk (24:30) ServiceNow and the AI Revolution (27:03) Building a Transparent and Collaborative Culture (29:37) Recruiting Top AI Talent (31:59) Navigating Market Realities and Customer Focus (37:59) Advice for Aspiring Founders

In this episode of Founded & Funded, Madrona Managing Director Soma Somasegar sits down with Anoop Gupta, co-founder and CEO of  @SeekOut    — an AI-first company transforming how organizations discover, hire, and manage talent.

They explore: 1) SeekOut’s evolution from LLM-powered workflows to the launch of SeekOut Spot, their agentic AI solution that delivers hires in as little as 3 days. 2) Why "service as software" is the future of recruiting. 3) How founders and talent leaders can reimagine hiring in the age of AI agents. 4) Lessons from building an AI-native company through market shifts. 5) The real business model shift from tools to outcomes.

With customers like Discord, 1Password, HP, and even Madrona itself, SeekOut is redefining what fast, high-quality hiring looks like.

Transcript: https://madrona.com/rise-of-agentic-ai-in-recruiting-seekout-anoop-gupta

Chapters: (00:00) Introduction (01:56) SeekOut Background and AI Evolution (03:55) The Role of Agentic AI in Recruiting (07:59) Business Model and Flexibility (12:59) Recruiting Process and Efficiency (16:49) Navigating Challenges and Product-Market Fit (20:29) Focus on Outcomes not on Hype  (22:25) Do you Need a Data Moat? (23:45) Don't build a recruiting org too early (25:50) The biggest hiring mistakes (29:15) Agentic AI for recruiting is here

This bonus episode of Founded & Funded is a follow-up to Madrona Partner Jon Turow's conversation with Douwe Kiela, CEO of Contextual AI and co-inventor of RAG.

In this quick chat, they dive into:

1) Why storytelling—not just GTM—needs to be vertical2) How to build a platform by showing what’s possible3) The tension between “doing one thing well” vs. building the whole stack 4) Multimodal content moderation at Meta & what it taught Douwe

This 10-minute post-show chat is a must-listen for founders thinking deeply about where to plant your flag — and when to break the rules.

​Microsoft Chairman & CEO Satya Nadella sat down with Madrona Managing Director Soma Somasegar at Madrona’s 2025 Annual Meeting to discuss the key inflection points in his leadership journey, Microsoft’s AI strategy, and the massive economic impact AI will have on the world. From redefining company culture to betting big on AI and OpenAI,Satya shares deep insights into Microsoft’s transformation — and what’s next.

Watch now for leadership lessons, AI predictions, and the future of innovation!

Transcript: https://www.madrona.com/satya-nadella-microsfot-ai-strategy-leadership-culture-computing

Chapters:

(00:00) Introduction (03:34) Satya Nadella's Journey as CEO  (09:57) Cultural Transformation at Microsoft (14:03) The Influence of Cricket on Leadership (18:27) The AI Revolution and Microsoft's Role (28:30) The Future of AI and Economic Impact

What does it take to invent a foundational AI paradigm — and then build a company to bring it to the enterprise?

In this episode of Founded & Funded, Madrona Partner Jon Turow sits down with Douwe Kiela, co-founder and CEO of Contextual AI and the co-inventor of RAG (Retrieval Augmented Generation). They dive into the origins of RAG, its misunderstood role in the enterprise, and how Contextual is redefining what production-grade AI systems can do. Douwe shares what most companies get wrong about RAG, why chunking shouldn't matter, how to think about hallucinations, and what founders need to know in the era of RAG agents.

Transcript: https://madrona.com/rag-inventor-talks-agents-grounded-ai-and-enterprise-impact

Chapters:

(00:00) Introduction  (01:27) The Origin of RAG (04:00) Challenges and Innovations in RAG (09:49) Enterprise Adoption and Use Cases (20:46) Scaling and Innovations at Contextual AI (23:39) The Future of RAG Agents (24:43) Challenges in Enterprise Data  (26:34) Building a Research-Driven Company (27:55) The Intersection of Research and Product (32:10) Advice for Founders and AI Companies (38:14) Understanding and Addressing Hallucinations (40:50) Company Building is Harder Than You’d Think (42:00) The Importance of Evaluation in AI (44:14) Concluding Thoughts

The security industry has a math problem: 12 million job postings, only 7 million qualified professionals. The solution? AI.

Edward Wu spent nearly a decade at ExtraHop, pioneering AI-driven security detection. But instead of just alerting security teams about potential threats, he saw a bigger opportunity — what if AI could act as an actual security analyst? That question led to Dropzone, a company that’s not just throwing AI at security but strategically using it to solve one of the most overwhelming problems in the industry — alert fatigue.

In this episode of Founded & Funded, Edward and Partner Vivek Ramaswami dive into:

• The "aha moment" that led Edward to leave a successful career to start Dropzone 
• Why most AI security startups will fail, and what it takes to stand out
• How Dropzone landed UiPath as a customer—without a single cold email 
• The future of security in an AI-first world

Watch/Listen to the full conversation for insights from Edward on what it takes to build in one of the most competitive categories in security today.

Transcript: https://www.madrona.com/dropzones-edward-wu-security/

 

Chapters: 

(00:00) Introduction (01:40) Edward Wu's Journey into Security (02:48) The ExtraHop Experience (05:10) The Leap to Entrepreneurship (07:59) The Aha Moment: Founding Dropzone (10:28) AI's Role in Security (16:30) Navigating the Competitive Landscape (19:15) Marketing and Customer Acquisition Strategies (21:30) Landing a big-name customer without cold outreach (25:40) Push v. pull when selling into security (28:25) ChatGPT was startups' greatest marketing gift (30:18) Lessons Learned as a Solo Founder

The biggest AI breakthroughs won’t come from Ph.D. labs — they’ll come from people solving real-world problems. So how do AI founders actually turn cutting-edge research into real products and scale them? In this week’s episode of Founded & Funded, Madrona Partner Jon Turow sat down with Jonathan Frankle, Chief AI Scientist at Databricks to talk about the shift from AI hype to real adoption — and what founders need to know.

They dive into: 

1) How AI adoption has shifted from hype to real-world production 

2) The #1 mistake AI startups make when trying to sell to enterprises 

3) Why your AI system shouldn’t care if it’s RAG, fine-tuned, or RLHF — it just needs to work 

4) The unexpected secret to getting your first customers 5) The AI opportunity that most startups are overlooking 

Transcript: https://www.madrona.com/databricks-ia40-ai-data-jonathan-frankle

Chapters:

(00:00) Introduction  (01:02) The Vision Behind MosaicML (04:11) Expanding the Mission at Databricks (05:52) The Concept of Data Intelligence (07:42) Navigating the AI Hype Cycle (15:10) Lessons from Early Wins at MosaicML  (20:50) Building a Strong AI Team (23:36) The Future of AI and Its Challenges  (24:06) Evolving Roles in AI at Databricks (25:55) Bridging Research and Product (28:29) High School Track at NeurIPS (30:39) AI Techniques and Customer Needs (38:22) Rapid Fire Questions and Lessons Learned (42:49) Exciting Trends in AI and Robotics (45:40) AI Policy and Governance

Thinking about leaving Big Tech for a startup? In this episode of Founded & Funded, Madrona Managing Director Tim Porter sits down with Bhrighu Sareen, who took the leap from Microsoft to Highspot and has been leading AI-driven product innovation ever since. They talk about the realities of transitioning from a massive company to a high-growth startup, scaling AI-driven teams, and how Bhrighu’s helping transform sales enablement through automation and intelligence. 

His insights on navigating change, working with founders, and executing at speed are a must-listen for any leader considering the leap from stability to startup chaos. Tune in now for practical strategies and an inside look at how AI is reshaping go-to-market execution. 

Transcript: https://www.madrona.com/big-tech-to-startups-highspot-bhrighu-sareen Chapters:

00:00 Introduction 03:01 Bhrigu Sareen's Journey at Microsoft 06:52 Transition to Highspot 10:00 Working with Founders and Building Trust 16:31 Increasing Product Velocity and Efficiency 21:12 Cross-Team Dependencies and Offshore Strategies 23:02 Starting the Journey at Highspot 23:31 Navigating Economic Uncertainty 24:21 Expanding Talent Pool in Vancouver 25:37 Establishing a Development Center in India 27:54 Challenges and Surprises in Transition 29:50 Innovating Through Economic Challenges 31:01 HighSpot's AI and ML Innovations 33:03 AI-Powered Sales Training and Coaching 36:14 Future of AI in Sales and Marketing 43:31 Balancing Data and User Experience 47:28 Looking Ahead: AI Agents and Productivity Gains

What does it take to go from engineer to founder, from startup CEO to scale CEO? In this special live episode of Founded & Funded, Madrona Managing Director Karan Mehandru sits down with Mohit Aron, founder of Nutanix and Cohesity, to uncover the lessons behind his success. Mohit shares his unique hiring strategy, how to identify product-market fit, and the power of balancing vision with execution. Whether you’re navigating your first company or scaling your third, Mohit’s advice is a masterclass in resilience, grit, and building a legacy.

Full Transcript: https://bit.ly/42xnyD9

Chapters:  (00:00) Introduction  (02:04) Traits of Successful Founders  (05:03) Challenges in Transitioning from CTO to Startup CEO to Scaling CEO  (07:51) Effective Hiring Strategies (13:42) Defining Product-Market Fit 15:55 Balancing Vision and Focus  (17:48) The Importance of a Bigger Vision  (20:12) The Role of a CEO Post Product-Market Fit  (22:00) Delegation and Leadership Strategies  (24:23) Generative AI: Hype vs. Reality  (27:09) Crafting a Vision and Minimum Lovable Product  (28:56) Choosing the Right Investors and Building a Board  (32:15) Framework for Startup Success