Brendon Bennett smiling in a baseball cap

Still convinced I’ve got one more good season in me.

Hi, I’m Brendon.

I’ve spent 25 years at Microsoft making complicated software make sense. My favorite spot is where content, design, and engineering overlap. I turn what we learn there into things teams actually reuse: terms, patterns, guidelines, and lately AI tools that catch content problems before they ship. The tools are fast. I’m still the one who makes the call, mostly because robots can’t sit through meetings. Yet.

See my work

Five moves upstream

From fixing words after they shipped to shaping them before they’re built.

#1

The classroom

Middle school English teacher and department head

Learned: How to explain hard things to people who hadn’t asked.

#2

The docs

Senior Technical Editor and Managing Editor, Exchange Server, 2001 to 2013

Before: Explaining confusing UI after it shipped.

After: Helped build a tool connected to code so editors could fix strings before release.

#3

The product

Senior Content Developer, Office 365, 2013 to 2014

Before: Documenting around confusing UI.

After: Asked product teams to let me write the UI, before that role existed in the org.

#4

The code

Senior UX Writer, Microsoft 365 security and compliance, 2014 to 2022

Before: Designed content only in tools like PowerPoint and Visio, never in the code.

After: Pioneered editing strings right in the codebase.

#5

The tools

Principal Content Designer, Microsoft Purview and Microsoft Security, 2022 to 2026

Before: Features without content design funding shipped without review, and often drove the most support issues.

After: Built AI tools that check content and suggest fixes against Microsoft and product standards before it merges.

Off the clock

I’m a husband to my soulmate and a dad to two grown kids and a wily corgi. Away from work, I’m usually traveling, at a game, concert, comedy show, or trying to win back some old glory on a pitch, court, diamond, or slope without breaking anything. I’ve also been writing the same short book for years. It’s still short.

I’m looking for a principal or senior content design role, remote or Seattle area hybrid.