Bhaskar Sunkara helped build AppDynamics from a laptop on a couch to a $3.7 billion Cisco acquisition.
Bhaskar Sunkara was employee number one and founding CTO at AppDynamics. Over nearly a decade, he helped turn the company into a category-defining application performance monitoring platform before Cisco acquired it on the eve of its planned IPO. He is now CEO of Bicycle, where he is building AI analytics agents for revenue-critical business data.
This conversation centers on a hard shift in enterprise software: moving from systems that display information to systems that detect problems, explain causes, and take action. Bhaskar argues that dashboard-driven operations are dying because no team can manually monitor every product, region, supplier, conversion path, and technical dependency in real time.
He makes the same critique of chat-based analytics. Letting users ask questions in plain English improves access to data, but it still depends on someone asking the right question at the right time. Bicycle takes a different approach. Its agents monitor business signals such as bookings, checkout conversion, payment approvals, and orders, then work through a decision tree spanning technical, commercial, supplier, inventory, pricing, and external factors.
The discussion also breaks down how Bhaskar and the AppDynamics team created focus before scale. They narrowed the product to Java, sold to operations rather than developers, built specifically for production, and used production proofs of concept to establish trust. That confidence eventually led to a self-service product customers deployed in production without assistance.
Bhaskar also explains why Bicycle chose transactional industries including travel, retail, and payments, where delayed decisions directly translate into lost revenue. He walks through the company’s “DEAL” framework: detect, explain, act, and learn.
In Today’s Episode We Discuss
- 00:01Introducing Bhaskar Sunkara
- 00:24From India to Silicon Valley
- 03:59Lessons from Building AppDynamics
- 07:10Why DevOps Remains a Fuzzy Concept
- 08:52Selling to Operations Instead of Developers
- 10:20Running Proofs of Concept in Production
- 12:21Launching AppDynamics Lite as a Self-Service Product
- 14:23Cisco’s $3.7 Billion AppDynamics Acquisition
- 16:34Learning Enterprise Scale Inside Cisco
- 18:05The Origin of Bicycle
- 19:42Turning Business Signals Into Action
- 21:47From Business IQ to Proactive Analytics
- 23:43Moving from CTO to CEO
- 25:08Bicycle’s Product Evolution
- 28:38Choosing Travel, Retail, and Payments
- 31:21Reducing Resolution Times Across 45,000 Locations
- 34:49Why Dashboard-Driven Operations Are Dying
- 37:01Why Companies Are Over-Indexing on Chat
- 40:03Selling Analytics to Business and Data Teams
- 42:00Building the Cursor for Analytics Teams
- 43:36How AI Is Changing Product Development
- 46:23Prototyping Products With Claude
- 47:27Bicycle’s Long-Term Vision
- 50:01Rapid-Fire Founder Lessons
- 53:23The Most Overrated Startup Metric
Pull Quotes
“Dashboard operations driven by dashboards are kind of dying.”
“You have to get the revenue back on track. You’re losing money.”
Follow Bhaskar Sunkara on LinkedIn: LinkedIn