Fractional C-level & executive consulting
Fractional CPO, CTO, CMO, and GM leadership for founders through established enterprises.
Senior operators who have done the job before — in the seat, owning the outcome, and focused on getting you there sooner. Plus management transformation and AI enablement.
Why Caldermont
We take the seat, own the number, and do the work — not a deck about the work. A proven operator embeds with your team and is accountable for the outcome.
A fractional engagement puts senior leadership in the seat in days, at a fraction of the cost, without the six months an executive search takes.
Every engagement ends with a stronger team, a documented operating system, and a clean transition to your full-time leader on your timeline.
What we do
Fractional leadership
Fractional CPO, CTO, CMO, and GM engagements. Part-time retainer, full accountability for the function's outcomes, and a hiring plan that graduates to your full-time leader.
Management transformation
Operating cadence, decision rights, planning and prioritization, cross-functional handoffs, and the metrics that prove the new system is working.
AI enablement
The productized practice: the AI-Enabled Organization curriculum, the prd-writer skill, and the 6-week rollout that teaches every team to hand work to the next with zero rework.
Product strategy, roadmap, and PM org design and coaching.
Architecture, engineering leadership, technical hiring, and delivery.
Positioning, demand generation, brand, and the marketing org.
To solidify good practices, execution and acceleration.
About
Caldermont Management is a fractional C-level and executive consulting firm. We place proven operators into the leadership seats a company needs before it can justify — or attract — the full-time hire: Chief Product Officer, Chief Technology Officer, Chief Marketing Officer, and General Manager.
Alongside fractional leadership, we run management-transformation engagements that rebuild how leadership teams plan, decide, and execute, and an AI-enablement practice that turns scattered AI experiments into one fast, coordinated organization.
The firm is led by Robert (Bob) Joseph Shaker II, an AI-forward product and technology executive with more than 30 years building, scaling, and transforming cybersecurity and software businesses — most recently as Chief Product and Technology Officer at ActiveState, and across four private-equity-backed businesses scaled from $10M to more than $500M.
Every engagement is measured the same way: the outcomes you were already working toward, reached sooner.
Principal
Engagement model
Contact
Tell us the outcome you're after and the timeline that matters, and we'll come back with the shape of an engagement and who would take the seat.