Chris Orlob

Current role at Caliber

Chris Orlob is the founder and CEO of Caliber, the sales and revenue skill-development company formerly known as pclub.io. Caliber's site describes training and technology for sales teams and individual sellers: it identifies skill gaps, closes them with training paths built by experienced revenue operators, and reinforces them with what it calls an AI Reinforcement Engine.^[1]

The offering has three pillars, training paths and certifications, AI-powered simulations, and hands-on enablement services. Businesses buy through a skills platform, a Value-Based Discovery training program and enablement services, while individuals follow role-based paths for account executives, SDRs, sales leaders, founders and people entering tech sales. The company says more than 20,000 sellers and teams use it and that Orlob has trained over 20,000 sellers. Its customer testimonials, such as higher close rates and larger deals, are self-reported by the vendor and unaudited.^[1]

From pclub.io to Caliber

Gong's author page, from earlier in the company's life, describes Orlob as co-founder and CEO of Pclub.io, a sales training platform that at that time coached more than 11,000 SaaS sellers. Caliber's current site shows the same business operating under a new name with a larger claimed reach.^[2][1]

Gong: from product marketing to revenue

Orlob had founded an earlier startup that Gong competed with. A podcast interview from January 2024 says he was then offered a job at Gong as Product Marketing Director, an unusual move from competitor to employee. The interview does not name the startup or give dates.^[3]

Gong's author page says he played a pivotal role as the company grew from about $200,000 to $200 million in annual recurring revenue, a period tied to a $7.2 billion valuation. It credits him with leading the creation of Gong Labs and with a series of go-to-market roles. The ARR and valuation figures are as stated on Gong's and Caliber's own pages, which describe his contribution but do not break down his share.^[2][1]

Leaving to teach

An episode title from the same podcast describes him as having left Gong to start two companies.^[3]

How he teaches

Caliber's flagship program is Value-Based Discovery, a training path on how sellers run the early customer conversation. The emphasis is on practice and reinforcement rather than one-off workshops, and the company pairs human-built curricula with AI simulations that let sellers rehearse calls.^[1]

Why he matters

Orlob is a prominent example of a go-to-market operator who turned in-house expertise into a standalone training business. His reputation rests on his Gong tenure and his current company applies that to skill development for sellers at companies of many sizes.^[1][2]

On The Executive List

Chris Orlob is ranked No. 82 on The Executive List (October 2026) in the Chief Strategy Officers discipline. The list row shows PClub; the company now operates as Caliber (formerly pclub.io), where he is founder and CEO. The ranking reflects The Executive Review's own editorial Trending Score; it is not an outside award, and placement on the list is never sold. View the October 2026 edition.