Today’s Agenda
Hey crew, I’m updating the email branding of The DesAI Digest. Let me know what you think.
This week, we’ll cover:
🛠 Career Strategy: How to Position Yourself as a Chief of Staff
⚡ Execution Insight: Launching Outbound: Automating Your Go-To-Market Approach
💼 Job Board: Payroll, People Programs, & Public Safety
Let’s dive in.
CAREER STRATEGY
How to Position Yourself as a Chief of Staff
I sat down with Tom Guthrie, Scott Amenta, and Lauren Werner from the Chief of Staff Network to talk about something that comes up constantly in the CoSN community: how do you actually land a Chief of Staff role?
A few things to highlight from the conversation:
1️⃣ I have reviewed thousands of CoS resumes. The ones that stand out don't just list responsibilities. They tie everything to commercial outcomes. Not "I ran the all hands" but "I ran the all hands and we retained staff by X% above industry benchmarks."
2️⃣ Tom made the case that CoS candidates need to be five-tool players: analytical horsepower, people skills, industry knowledge, stage experience, and now real AI capabilities. You don't have to be elite at all five. But you can't be missing one entirely.
3️⃣ And Lauren said something that might resonate: every person she talked to told her she was a Chief of Staff before she believed it herself. A lot of people are doing this work already under a different title.
EXECUTION INSIGHT
Launching Outbound: Automating Your Go-To-Market Approach
I recently walked a group of early-stage founders through a simple goal: launch your first outbound campaign in one week.
The focus wasn’t on hacks or fancy tools, but getting the basics right:
Get clear on exactly who you want to reach.
Identify a real reason to contact them.
Make a specific, helpful offer instead of asking for “15 minutes to chat.”
And ensure you have the infrastructure to enable those steps: set up a clean sending domain, build a small, high-quality list, write a short sequence, and send to a small batch so you can learn before scaling.
If you want the slides that walk you through everything, just sign up for the newsletter :)JOB BOARD
Payroll, People Programs, & Public Safety
Here are the 3 most interesting remote job openings I’ve seen this week, all paying $150k or more:
If you want the jobs, please sign up for the newsletter :) That’s it for this week.
-Rahul from The DesAI Digest
P.S. Reply back to this email with a business challenge you’re facing! I’d love to help.
P.P.S. if you liked this, forward it to a friend. And if you hated it, forward it to an enemy.
