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Chris Orlob on the TechTO stage

Chris Orlob

Co-founder & CEO, Caliber

Sales TechOn TechTO stages since 2019

Chris Orlob is co-founder and CEO of Caliber, the B2B sales-training company formerly called pclub.io. He spent six years at Gong.io — first in product marketing, then leading sales — while it grew from $200K to $200M in ARR. He joined a SalesTO panel in Toronto in 2019 on how go-to-market teams win together.

On the TechTO stage ×1

First seen on the TechTO stage in 2019. Every talk is searchable — ask the archive about Chris

In their words

if I could condense our entire approach to content strategy to four bullet points it would be: understand your audience, read every day, write every day, write every goddamn day.

TechTO SalesTO, Sep 2019 · watch at 11:39

the first one is the most important. You can write, you can come up with ideas, but if you don't understand your audience's pain, their objections — essentially their soul — then you're just kind of guessing.

TechTO SalesTO, Sep 2019 · watch at 12:04

I think the takeaway is interview at least a few of them. Start off with like three interviews a month for a few months and you'll blow past your peers.

TechTO SalesTO, Sep 2019 · watch at 13:44
A few quotes can’t cover everything Chris said on the TechTO stage. 1,600+ talks are searchable.Ask about Chris

Around the web ×2

Quick answers

Who is Chris Orlob?

Co-founder and CEO of Caliber, a B2B sales-training company that was previously called pclub.io. Before that he spent six years at Gong.io in product marketing and sales leadership, joining at roughly $200K ARR and leaving in 2022 at $200M.

What did Chris Orlob speak about at SalesTO?

He was on the September 2019 'Revenue success' panel in Toronto with Ryan Barretto of Sprout Social and Erin Bush of LeanData, on selling as a team rather than as individuals. His section covered how Gong built its content engine.

What is Chris Orlob's advice on content?

Understand the audience before anything else. He interviewed roughly 250 VPs of sales while running a startup that competed with Gong, and says the transferable version is three customer interviews a month.

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Maintained by TechTO · facts sourced and dated · last reviewed Aug 20, 2026