About us

Who takes the seat, and how the engagement runs.

Caldermont Management fills the leadership seats a company needs before it can make the full-time hire: Chief Product Officer, Chief Technology Officer, Chief Marketing Officer, and General Manager. The person in your seat works inside your systems and policies, on a project or retainer, with full accountability for the function.

Not every gap is an executive seat. When a company needs product management some of the time but cannot afford, justify, or fill a full-time product manager's seat, a working product manager from Caldermont does the job: discovery, the roadmap, the requirements, and the launches, for as long as the gap lasts.

When the leaders are in place but the company still moves slowly, management transformation rebuilds how the leadership team plans, decides, and executes. When every team needs to work with AI, The AI-Enabled Organization teaches all 13 functions to do it, and to hand work to each other without rework.

The firm is led by Robert (Bob) Joseph Shaker II, who has spent more than 25 years building, scaling, and transforming cybersecurity and software businesses, including four private-equity-backed businesses scaled from zero to more than $100M. He has taken margins from negative EBITDA to profitability, built product and engineering organizations from the ground up, and moved customer retention from 60% to above 90%. That is the experience behind every seat we fill.

Every engagement is measured the same way: the outcomes you were already working toward, reached sooner.

Engagement model

  • Project or retainer based, with full accountability for the outcome
  • Within your systems and policies
  • Built to hand off to your full-time leader, on your timeline
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A range of snow-covered peaks in cool evening light
  • Project or retainer
  • Inside your systems
  • Built to hand off

Our team

The people who take the seat.

Caldermont is small by design. The person you meet is the person who takes the seat. Here is who that is today.

Portrait of Robert (Bob) Joseph Shaker II, Founder and Managing Director of Caldermont Management

Founder and Managing Director

Robert (Bob) Joseph Shaker II

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Bob Shaker founded Caldermont Management and takes the seat himself. He has led product, engineering, and managed services at ActiveState, Trellix, Malwarebytes, and Symantec, and spent seven years as Wellington Management's Chief Information Security Officer.

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.

Bob holds a B.S. from the University of Massachusetts and is the inventor on U.S. Patent 10,466,924, systems and methods for generating memory images of computing devices.