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 30 years building, scaling, and transforming cybersecurity and software businesses, including four businesses built from zero, one of them to $100M. He has taken margins from negative EBITDA to profitability across four private-equity-backed companies, 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 management 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.

Founder and Managing Director

Robert (Bob) Joseph Shaker II

Full profile Connect on LinkedIn rshaker@caldermontmanagement.com

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 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.

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.

Our staff

The people who make it stick.

Taking the seat is the start. These are the people who make sure the work lands with the customers who have to live with it.

Customer Experience Advisor

Jeff Walton

Jeff Walton helps Caldermont turn new customers into lasting ones. He built his approach from both sides of the table: sixteen years as the customer running the technology, then as the person accountable for making other customers successful.

He started as the customer. For sixteen years he led point-of-sale rollouts, large-format print and raster image processor deployments, and security remediation for a retail and e-commerce brand. He saw implementations that worked and implementations that failed, and he learned what customers remember long after the contract is signed. As he puts it, "I don't just understand the lifecycle. I've lived it."

Those lessons came together at Malwarebytes, where Bob Shaker recruited him as a founding member of the Managed Security Services business. Handed a blank page, Jeff built the global onboarding program from scratch, serving enterprise accounts directly and smaller businesses through digital journeys and managed service provider partners. It held customer retention at 90% and an enablement rate of 88% across more than 1,300 customers.

Today he helps leadership teams design customer experience programs, build and coach customer success and enablement teams, and set the operating rhythms that make results repeatable. The work rests on one belief: a customer's first 90 days decide how the next three years go. His clients get clear stage gates, training that teaches people their jobs rather than just the software, and hand-offs that never make a customer repeat themselves.

Jeff holds a B.A. in Theater Arts and Film from Humboldt State University, which taught him that good training is also a good performance. At Caldermont he has one goal: customers who run the product with confidence and stay because it works.

Engineering Lead

Todd Cook

Todd Cook is an engineering leader focused on engineering transformation, AI adoption and clearing technical debt. More than fifteen years in software engineering took him from developer to engineering leader, and taught him that new tools only pay off when the operating model around them changes too.

Most recently he was Director of Engineering at ActiveState, where he led the engineering organization through both a company-wide strategic pivot to a new product and a transformation to an AI-native workflow. He focused on AI governance for approved tooling, cost accountability, and onboarding engineers into new patterns and processes. Engineering productivity rose 30 to 50%, deployment frequency rose 50%, and pull request review lead time fell to between four and six hours. His organization implemented an agentic software development lifecycle with explicit human design and approval gates, and piloted an agentic software factory covering architecture, engineering, quality assurance and security, from definition to production.

Todd has led engineering for products and platforms in healthcare, cybersecurity and regulated manufacturing, and brings an engineer's practical view to every engagement. AI adoption works when it is deliberate, measured and governed. It does not work when novelty drives it. His clients get clear guardrails, adoption tied to real delivery metrics, and managers equipped to lead the change rather than wait for it.

Todd holds a B.F.A. in Digital Art from the University of Tampa, with certificates in User Experience Design from the Nielsen Norman Group and in Human-Centered Design from the Luma Institute.

Head of Human Resource Practice

Laura Klieves

Laura Klieves is a strategic HR executive who thrives at the intersection of human resources, business leadership, and communications. A hands-on thinker-doer, she pairs strategic perspective with a decisive, fair leadership style that drives clarity, accountability, and results while building workplaces where people thrive.

Laura has led transformational initiatives across global HR operations, private equity partnerships, and M&A. At Malwarebytes where she was the VP Global People, Laura led an 18-person global HR team supporting 700+ employees in the US, Canada, South America, Australia, and 21 EMEA countries, navigating a strategic separation, workforce reductions, and multi-million-dollar cost savings. Previously, she grew Duarte's Academy business unit eightfold over nine consecutiveyears, building training programs that set industry benchmarks.

Executive Career Highlights: Spearheaded the separation of Malwarebytes into two independent companies, ensuring operational continuity across regions, directed private equity integrations and M &A due diligence in Israel, the US, and Sweden, reduced people-related expenses by $49.5M during workforce realignments while preserving engagement and stability, scaled Duarte's Academy eightfold over nine years, expanding its global market reach.

Beyond the corporate arena, Laura is deeply committed to mentorship. She served as a Girl Scout leader for 16 years and a Boy Scout leader for 12, guiding both her children to their programs' highest awards. As Chair of the Development and Communications Committee for the Rosie the Riveter Trust, she elevates the stories of the women who worked on the WWII home front, connecting their legacy to today's Rosies in the trades and beyond.

Known for direct, decisive leadership that inspires loyalty and high performance, Laura rolls up her sleeves to solve complex challenges while maintaining a clear strategic vision that connects business goals with human potential.