Latest · Organizational AI
Individual AI fluency isn't making your company faster
Most organizations bolt AI onto the person. The gains that actually compound come from the handoffs between teams.
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 25 years building, scaling, and transforming cybersecurity and software businesses. Founder and Managing Director of Caldermont Management, where he takes the seat himself.
25+
Years building, scaling, and transforming software & security businesses
$0 $100M+
Four private-equity-backed businesses scaled, at 12 to 50% a year
85%
Faster time to market, delivering a company's first new production-ready products
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 25 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 has served as Senior Vice President of Product and Engineering at ActiveState, where he restructured product and engineering into an AI-native organization, cut time to market by 85%, and rebuilt the company's 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 roadmap and launched an AI-native analyst inside the endpoint portfolio.
At Malwarebytes he owned the P&L for products and managed services and built the MDR business from concept to profitability, with margins above 90% and customer retention moved from roughly 60% to more than 90%. Over a decade at Symantec and NortonLifeLock he launched five managed services and products with combined revenue of more than $100M, after nearly five years as Symantec's Field CTO. Earlier he spent seven years as Vice President and Chief Information Security Officer at Wellington Management, and began his career as Security Solutions Director at Burntsand.
Across his career he has scaled four private-equity-backed businesses from zero to more than $100M, built product and engineering organizations from the ground up, and taken margins from negative EBITDA to profitability. 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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