Startup to Scale: A Mini Masterclass in Efficient Growth and GTM
Release Date: 09/16/2024
Breaking into Enterprise: How Anagram Landed Disney with Cold Outbound
Founded & Funded
In the latest episode of Founded & Funded, Madrona Partner Vivek Ramaswami sits down with Harley Sugarman, founder and CEO of Anagram, to unpack how one pivot, a flood of cold outreach, and relentless focus on behavior change transformed a niche tool into an enterprise platform serving companies like Disney and Pfizer. From landing enterprise logos off of nothing but wireframes, to outmaneuvering the 800-lb gorilla in a legacy industry — Harley's tactics are a masterclass for any founder trying to stand out in a crowded market. Transcript:...
info_outline
Building Biotech in Seattle: Madrona Investor Spotlight with Joe Horsman
Founded & Funded
What happens when a scientist becomes a VC? We sat down with Madrona’s Joe Horsman to find out. In this episode, Joe shares his journey from late nights in the lab to helping biotech founders bring life-changing science to market. You’ll hear: Why Seattle’s biotech + AI ecosystem is heating up What founders need beyond funding to commercialize world-changing science. Why weekend adventures fuel Monday creativity
info_outline
The End of Biz Apps? AI, Agility, and The Agent-Native Enterprise from Microsoft CVP Charles Lamanna
Founded & Funded
In this Founded & Funded episode, Madrona Managing Director Soma Somasegar sits down with Charles Lamanna, Corporate Vice President at Microsoft, to unpack his journey from startup founder to corporate leader. They dive into what it takes to build a successful AI-transformed organization, how the nature of business applications is evolving, and why AI agents will fundamentally reshape teams, tools, and workflows. From "customer obsession" to "extreme ownership," Charles delivers insight after insight for startup founders and enterprise leaders navigating the age of AI. They dive into: Why...
info_outline
Building AI That Sells: Scaling Smarter with Luminance CEO Eleanor Lightbody
Founded & Funded
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: Chapters: (00:00) Introduction (01:29) Eleanor's Career Journey (03:22)...
info_outline
Customer Obsession & Agentic AI Power Ravenna’s Reinvention of Internal Ops
Founded & Funded
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+...
info_outline
Reinventing Recruiting: SeekOut’s Anoop Gupta on the Rise of Agentic AI
Founded & Funded
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...
info_outline
Unscripted: What Happened After the Mic Went Off with Douwe Kiela
Founded & Funded
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....
info_outline
AI, Ambition, and a $3 Trillion Vision: Satya Nadella on Microsoft’s Bold Bet
Founded & Funded
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:...
info_outline
RAG Inventor Talks Agents, Grounded AI, and Enterprise Impact
Founded & Funded
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...
info_outline
Dropzone’s Edward Wu on Solving Security’s Biggest Bottleneck
Founded & Funded
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,...
info_outlineIn the latest episode of Founded & Funded, Madrona Managing Director Tim Porter hosts Pradeep Rathinam, a seasoned software executive with over three decades of leadership experience. Paddy was the Founder and CEO of Madrona portfolio company AnswerIQ, which Madrona invested in back in 2017. It was one of the early machine learning applied to SaaS companies that Madrona invested in. Paddy sold AnswerIQ in 2020 to Freshworks, where he started out as chief customer officer, helped take the company public, became chief revenue officer, and really drove a series of incredible accomplishments for Freshworks.
Today, Tim and Paddy dive into that world of SaaS go-to-market. Paddy shares his experiences on how to not just grow a company, as every company needs to do, but how to grow efficiently and how that includes reducing churn, expanding accounts, and landing new logos. This is something that all go-to-market leaders and startup founders have a lot of questions about how to unlock, so it is a must-listen for founders.
View the full transcript here: https://www.madrona.com/startup-efficient-growth-gtm-pradeep-rathinam/
You can find Paddy's writings on these topics here: https://www.linkedin.com/in/paddyrathinam/recent-activity/articles/
Chapters:
(00:00) Introduction
(00:31) Meet Pradeep Rathinam
(01:36) The AnswerIQ Journey
(04:06) Joining Freshworks: Tackling Churn and Growth
(05:25) Efficient Growth Strategies
(06:10) Framework for Efficient Growth
(09:09) Challenges and Solutions in Sales Transformation
(14:12) Change Management and Organizational Alignment
(17:28) New Business Development
(23:01) Customer Retention Strategies
(36:05) Driving Expansion Within Accounts
(41:10) When to Hire a CRO