In this episode, Carlos Gonzalez de Villaumbrosia interviews Anneka Gupta, Chief Product Officer at Rubrik, a leading cybersecurity company helping over 5,000 customers, including half of the Fortune 500, protect and manage their data against cyber threats.

Under Anneka's leadership since 2021, Rubrik has undergone one of tech's most impressive product transformations, evolving from an IT backup solution into a comprehensive cybersecurity platform. This transformation has driven remarkable growth, with subscription ARR crossing $1.09 billion and the company successfully going public in 2024.

In this episode, we explore Rubrik's journey through three major transformations: shifting from perpetual licenses to a SaaS-first model, expanding from a single product to a multi-product platform (with two new product lines approaching $100M in ARR), and repositioning as a cybersecurity-first company. We'll dive deep into the challenges and strategies behind managing such significant organizational change at scale.

What you'll learn:

• How to successfully transition a business model from perpetual licenses to subscription
• Strategies for expanding from single-product to multi-product portfolio
• Methods for structuring teams around strategic pillars rather than just product lines
• Approaches to maintaining growth while managing significant organizational change
• Techniques for leveraging existing customer relationships to validate new products
• Frameworks for creating clear career progression during transformation

Key Takeaways👇:

• Business Model Transformation
• Successfully managed parallel tracks of maintaining core business while building new capabilities, growing from $100M to $1.1B ARR in 4 years.
• Portfolio Expansion Strategy
• Created specialized go-to-market teams for new product lines while leveraging existing customer base for validation and early adoption.
• Organizational Design
• Structured teams around strategic pillars (core business, public cloud, security, AI) with a dedicated platform team for cross-functional needs.
• Change Management
• Implemented transparent communication and clear career frameworks while setting firm deadlines for business model transition.
• Customer-Centric Innovation
• Used existing customer relationships to validate new product opportunities and guide portfolio expansion into cybersecurity.
  
  

This episode is essential listening for any product leader managing large-scale business transformation or considering major strategic shifts in their organization.

This episode is brought to you by Persona, the adaptable identity platform that helps businesses fight fraud, meet compliance requirements, and build trust. These days, it's easier than ever for fraudsters to steal voices, faces, and identities. That's where Persona comes in; helping leading companies to securely verify individuals and businesses worldwide, providing flexible building blocks to create tailored verification flows that maximize conversion while minimizing risks.
Whether you work at a startup or large enterprise, you can get started for free here: https://withpersona.com/productschool

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Credits:
Host: Carlos Gonzalez de Villaumbrosia
Guest: Anneka Gupta

In this episode, Carlos Gonzalez de Villaumbrosia interviews Vijaye Raji, Co-founder and CEO of Statsig, the fast-growing product experimentation platform recently valued at $1.1 billion following a $100M Series C round—and just acquired by OpenAI in a landmark $1.1B all-equity deal.

Before the acquisition, Vijaye spent over a decade at Facebook, where he served as VP and Head of Entertainment, launching creator tools, livestreaming features, and the earliest version of Reels. That experience inspired him to build Statsig, a platform that empowers product teams to experiment, iterate, and ship with confidence—used by leading companies like Microsoft and Notion.

Now, as OpenAI’s Chief Technology Officer of Applications, Vijaye will oversee product engineering for ChatGPT and help accelerate the company’s enterprise roadmap. In this conversation, he shares the original vision behind Statsig, the tough lessons from going multi-product, and why AI-native experimentation is the future of product building.

What you’ll learn:
- Vijaye’s journey from Facebook’s internal tools to OpenAI’s CTO of Applications.
- How Statsig evolved from an experimentation engine into a full decision-making stack.
- Why large enterprises are ditching homegrown tools for best-in-class platforms.
- How AI is powering everything from feature flagging to self-healing products.

Key Takeaways 👇
- From Startup to OpenAI: Why StatSig’s platform and customer base made it one of OpenAI’s largest acquisitions yet.
- AI as an Operating Layer: How Vijaye is thinking about AI-native observability, prompt evaluation, and synthetic user data.
- Scaling with Product-Led Growth: Lessons in going enterprise while keeping experimentation at the core.

Social Links:
- Follow our Podcast on Tik Tok here
- Follow Product School on LinkedIn here
- Join Product School's free events here
- Find out more about Product School here
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Credits:
Host: Carlos Gonzalez de Villaumbrosia
Guest: Vijaye Raji

In this episode, Carlos Gonzalez de Villaumbrosia interviews Inbal Shani, Chief Product Officer at Twilio, the $18B customer engagement powerhouse trusted by over 320,000 businesses worldwide.
Inbal is a trailblazer in AI-first product development. Before joining Twilio, she led the launch of GitHub Copilot—one of the most transformative AI tools for developers, reshaping how engineers write code. Now at Twilio, she’s steering a product portfolio that infuses AI into the heart of customer communications, helping companies unlock smarter, more personalized digital experiences at scale.
In this conversation, Inbal shares why successful AI adoption goes far beyond adding models to features—it requires a rethinking of product strategy itself. She also dives into how Twilio measures real business impact from AI, why PMs need technical fluency more than ever, and what it takes to lead a product org into the AI-native future.

What you’ll learn:
- How GitHub Copilot shaped Inbal’s approach to building AI-native products.
- Why AI adoption alone is not a product strategy—and what to focus on instead.
- The metrics Twilio uses to evaluate AI’s business impact.
- The evolving technical skill set required for PMs in the age of AI.

Key Takeaways👇:
- Beyond the Hype: Inbal’s perspective on what truly makes AI transformative for end users.
- AI as Strategy, Not Feature: How to align AI capabilities with customer outcomes.
- PMs in the AI Era: The must-have technical skills that will define tomorrow’s product leaders.

This episode is brought to you by Persona, the adaptable identity platform that helps businesses fight fraud, meet compliance requirements, and build trust. These days, it's easier than ever for fraudsters to steal voices, faces, and identities. That's where Persona comes in; helping leading companies to securely verify individuals and businesses worldwide, providing flexible building blocks to create tailored verification flows that maximize conversion while minimizing risks.
Whether you work at a startup or large enterprise, you can get started for free here: https://withpersona.com/productschool

Social Links:
- Follow our Podcast on Tik Tok here
- Follow Product School on LinkedIn here
- Join Product School's free events here
- Find out more about Product School here

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Credits:
Host: Carlos Gonzalez de Villaumbrosia
Guest: Inbal Shani