About Degy Entertainment

Degy Entertainment is a global booking agency for concerts and live events, known as one of the leading entertainment buyers in the world.

With a team of about 30, they book and execute nearly 3,000 events each year across 30 countries, which means the work depends on repeatable, detail-heavy processes behind the scenes.

Michael Silver is Degy’s Special Projects Director, and he’s often the person those processes funnel to.

If it’s not operations, sales, or accounting… it usually lands with me.

That means he’s constantly bouncing between web-based systems like ticketing, HR tools, internal platforms, helping people get unstuck.

The challenge

The biggest time sink wasn’t teaching. It was reteaching.

A Zoom walkthrough helps… once.

A week later, someone needs to do the same thing again. They don’t remember the steps. 

Or they remember most of the steps, which is even worse.

In ticketing, one missed checkbox can turn into a real mess.

Michael didn’t want to be the gatekeeper. But when the work lives in the details, delegating without a reliable process meant more errors, more follow-ups, and more of his time pulled into repeat explanations.

The workaround that didn’t scale

Michael’s first attempt to solve the repeat-training problem was the obvious one: record his screen and talk through the process.

It sounded simple, but in practice, it was frustrating and slow.

To create something shareable, he had to record full takes end-to-end. If he misspoke, clicked the wrong place, or something unexpected popped up, he’d have to restart, sometimes multiple times.

If something loads too slowly, or an unexpected popup shows up, the whole recording is basically toast.

And even when the video turned out well, it would need to be re-recorded if the process changed.

The shift: document it in real time

Michael found Trails and the experience felt different right away.

Instead of stopping work to “make training,” he could turn real work into documentation as he did it.

Within about an hour of creating an account, he was already building guides and sending them out.

And one feature changed everything: the pause button.

If something looks off, I pause, fix it, and keep going, no wasted takes.

Instead of re-recording from the beginning, Michael could correct issues in the moment and continue, keeping the guides and videos clean and accurate without the friction of starting over.

The result: self-serve answers and consistent execution

Today, Michael’s guides live in Trails.

The payoff is when the same question doesn’t come back.

Instead of pinging Michael for a refresher, his team reopens the guide in Trails, follows along on their own screen, and moves on.

It’s the difference between ‘I think I remember’ and ‘I can pull up the exact steps and do it right’.

For Michael, Trails makes creation faster and outcomes more consistent.

• 3× faster to create guides compared to his old workflow
• Less re-training because people can self-serve
• Faster onboarding for new team members

With new folks, I send the link and they usually don’t even have questions.

Delegation without losing standards

Michael’s work lives in the details: naming conventions, required fields, the one box you cannot miss. 

He likes that Trails lets him bake those standards into the guide itself with bold text, notes, and clear “don’t skip this” moments, so quality doesn’t drop when the work gets delegated.

And now the process document is the source of truth, not Michael’s calendar.