The Email That Got Him Fired, and What He Built After

Chris Pitchford was 23, the number one salesperson out of 300 on the floor, and about to lose his job over an email.

The deal was a big one. He had brought the customer into the office to meet his VP of Sales, and the meeting went badly. The customer worked in the diamond business. The VP, unluckily, picked that day to talk about an engagement ring. Friction followed.

“The meeting ends and my client says to me over email, I didn’t really like your VP of sales. The deal is off.”

Pitchford did what a lot of young salespeople would do. He tried to rescue it.

“I might have thrown my VP of sales a little bit under the bus,” he says. “Basically said, don’t worry about him. I understand there was a conflict. Just worry about me. It’s going to be fine.”

What he did not know was that the customer had history with his employer, one of the largest companies in Canada, and had been waiting years for exactly this kind of leverage.

“Once I wrote him this email, I wrote too much. I said too much. And he forwarded the email to a number of people. The email went all the way up to senior leadership, came back down to my boss and my boss’s boss and my boss’s boss’s boss. They all saw it, and they brought me in a room and they said, what the hell?”

He stood by what he had written. He was fired anyway.

“This customer screwed me over. He played me. He wanted that email. He provoked it, and it worked.”

The dropout who never planned to be an employee

The firing pushed him somewhere he had probably been heading anyway.

Pitchford had dropped out of university in Canada without a degree, having already bought a franchise and run small businesses while still a student. “That’s where I sort of learned how to be an entrepreneur,” he says. Both parents were entrepreneurial. Sales came easily, and he was good at it in an unorthodox way. “I was a bit of a lone wolf and sort of figured out my own ways to win.”

Losing the job clarified something.

“I realised I didn’t want to join another big company and just be a cog in the wheel.”

In 2015 he co-founded a software company called Shyft with the person he had bought his franchise from. It could not crack the US market, so it joined Techstars in Seattle for what was supposed to be three months, and that became the route into America instead. They raised six and a half million dollars in 2018. He left in 2019, because it was not working.

Two scoreboards, one company

The way he describes Shyft now is the most quietly useful thing he says.

“Shyft was a success for me. It really helped me,” he says. “But for venture capital standards, it was a failure.”

Both things are true at once, and founders rarely say so out loud. Shyft taught him how to build, got him into the US, and made him employable at a level he could not otherwise have reached. It also did not deliver the returns its investors were underwriting. Knowing which scoreboard is in use is a skill most people pick up much later than he did.

He joined Ally.io in 2019, and this time the ending was different. Microsoft acquired the company in October 2021, roughly three years into its life, folding the product into what became Viva Goals.

Ask what he took from the acquisition and he does not talk about money.

“To know what good looks like,” he says. “Now I know what great really looks like, and what that means in terms of how to run a company and have an actual liquidation event.”

The comparison is what makes it usable. “In my first startup, if you compare the things that we did versus this startup, it was night and day.”

“I’ve seen failure and I’ve seen success. So how to pattern match, I think, is the biggest benefit.”

An operator who has only seen things work has no control group. They cannot separate what caused the outcome from what merely came along with it. Pitchford has both data points, which is why he rates the company that failed as highly as the one that sold.

Falling in love with a customer, not an idea

Brev exists because of something that happened while he was still at Ally.

“I fell in love with the customer of this product, and the problem set that they were trying to solve. I became obsessed with it.”

The acquisition came fast, at three years old, which left a lot unfinished. “We had a lot of stones unturned that we didn’t solve, and a lot of visions for the future that are never going to get realised because Microsoft acquired the company.”

Then, at Microsoft, the technology changed underneath the problem. Copilot arrived. GPT arrived.

“That’s the inception story for Brev. All the experience and pain and challenges I heard from customers, plus new technology that’s now available.”

The problem he is aiming at is companies that set goals in January and quietly miss them by December.

“Why do companies exist? Companies exist to hit their targets. So if we’re missing them, it’s pretty important.”

What separates the companies that execute

Pressed on what actually drives execution, he gives a framework any leadership team could use tomorrow, independent of his software.

Focus. “Don’t do too many things. Just be focused on exactly the two or three things.” His reasoning is blunt. Even large companies attempting more than three priorities will “fall flat on a number of things”.

Agility, which he defines as course-correction speed rather than raw pace. “If it takes you six months to course correct on a problem, you’re not very agile. If it took you six days, you’re much, much faster.” Companies slow as they grow, he says, like the difference between turning an ocean liner and turning a speedboat.

He has watched it work at scale. During the pandemic, when live events stopped entirely, Ticketmaster used the product to reorient a 4,000-person business around a completely new strategy. “They said that next to Slack and Zoom, during the pandemic, our product was mission critical.”

For someone this fluent about other companies, the sharpest thing he says is about himself.

“I think I’ve got the story, I think I’ve got the credibility, and I think I do have a good network. But I need to do a better job giving, not taking. I take too much from my network. I need to give more.”