Product & technology leadership · AI enablement

Robert J Shaker II

Turning AI and emerging technology into category-leading products and profitable businesses.

An AI-forward product and technology executive with more than 30 years building, scaling, and transforming cybersecurity and software businesses. Founder and Managing Director of Caldermont Management, where he takes the seat himself.

  • CISSP
  • CGEIT
  • CRISC
  • CCSK (expired)
  • U.S. Patent 10,466,924
Portrait of Robert (Bob) Joseph Shaker II
30+
Years building, scaling, and transforming software & security businesses
$0 $100M
Symantec's managed detection and response, one of four businesses he built from zero
75%
Shorter ship times, from AI-driven tooling across product and engineering
60% 90%+
Customer retention, through product- and service-led engagement

Principles

Good product and technology practices, built for the age of AI.

The leverage is
in the handoffs

AI multiplies an organization the most not when one person prompts well in isolation, but when every team produces structured outputs the next team's AI can immediately consume.

Practice
over hype

Durable ways of working that outlast any single model, tool, or trend. The practices are the point; the tools change underneath them.

One source,
many deliverables

Start from a single, well-formed PRD and let every downstream team, engineering, go-to-market, and analysts, work from the same structured truth, rendered on-brand.

About

Bob Shaker

Bob Shaker is an AI-forward product and technology executive with more than 30 years building, scaling, and transforming cybersecurity and software businesses. He founded Caldermont Management and takes the seat himself: a leader who has held it before, working inside a client's systems from week one, with a plan to hand off.

Most recently he served as Chief Product and Technology Officer at ActiveState, where he rebuilt the engineering organization, introduced AI-assisted delivery that completed six months of roadmap in three weeks and shipped the company's first production-ready products, and rebuilt its analyst narrative around software supply chain security. Before that he was Vice President of XDR Product Management at Trellix, where he brought the FireEye and McAfee endpoint lines under one plan, worked with engineering to redesign the architecture across both technology stacks, and launched an AI-native analyst inside the endpoint portfolio.

At Malwarebytes he owned the P&L for products and managed services, built the managed detection and response business from concept to breakeven in under two years, designed the Snowflake and Amazon Web Services backend that cut time to detection from 10 minutes to under 60 seconds and saved $3M a year, and moved customer retention from roughly 60% to more than 90%. Over a decade at Symantec and NortonLifeLock, starting as Symantec's Field CTO, he launched five managed services and products, among them managed detection and response, built from zero to $100M, and managed network forensics, grown from $150M to $250M. At Norton he led the Safe Search transformation that took revenue from about $40M to more than $75M in 15 months. Earlier he spent seven years as Vice President and Chief Information Security Officer at Wellington Management, led security solutions at Primix and Burntsand, and began his career by founding MegaRam Technologies, which he sold to Impulz Labs.

Across his career he has built four businesses from zero, one of them to $100M, built product and engineering organizations of more than 50 people from the ground up, and taken margins from negative EBITDA to profitability across four private-equity-backed companies. His leadership reaches across product management, engineering, strategy, and go-to-market, with strong influence among industry analysts and customer CISOs.

Insights

Writing on the practices behind the work.

Connect

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