I'm baaaaaaaack!

Love is dead, but I lived to tell you about it.

If you’re wondering why The Offer Letter skipped a week, it’s because I was at sea. Emotionally, spiritually, and quite literally — on what was supposed to be a romantic sailing trip but instead turned into a floating existential crisis without wifi.

What I pictured: sunset pinot gris, stargazing sessions, the Starlink that was said to be included, maybe even a hard launch on social media.

What actually happened: nonstop nausea, the silent treatment at sea, a breakup while we had snorkels on, and me wondering if the ocean would accept me as one of its own.

The boat docked. He’s dead to me (emotionally, for legal reasons). And I am thrilled to be back at my desk, where nothing moves and no one tells me my “taste in music is terrible”. I’ve never been more grateful for capitalism’s cold embrace.

So yes, I’m back. Slightly sun-damaged, emotionally dehydrated, but ready to bring you another week of job market chaos, questionable advice, and career clarity from a woman who just redefined “rock bottom” at sea.

This week on The Offer Letter:

• Coolest Jobs!
• A pre-interview flex
• Is AI totally F-ing us?
  

P.S. - I will be Vanna White-ing the Chicagoland Admin Awards Gala tonight!! If you're going to be there and reading this, PLEASE COME SAY HI!

I DID get a pretty sweet instagram post out of it:

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🔥 This Week's Best Openings

I am not partnered with these companies, but if any of you get a job here, you know what to do! (Bring me on as a recruitment partner.)

•EA to the CEO – Jersey City, I ❤️ Nuts [Apply here]

•EA to CEO – ATX, I Also ❤️ Chips but...Brain Chips? [Apply here]

•Executive Administrative Partner – Fort Worth, Huge Company [Apply here]

🎯 Interview Tip of the Week: Show You Can Do the Job Before You Even Get It

Here’s a revolutionary concept: instead of telling them you’re proactive, just… be proactive.

Before your interview, do a little light internet stalking. (Creepy? Yes. Effective? Also yes.) Look at the exec’s LinkedIn and Facebook if you can find it, the company’s last press release, their painfully aspirational About Us page, and anything else that makes you think, this person is overwhelmed and possibly spiraling.

Then? Show up with a one-pager titled something like:

“3 Ways I’d Make Your Life Less Chaotic, Starting Immediately.”

Don’t overthink it. Examples:

•“Automate the weekly investor update using AI + templates so you stop sending it at 2 a.m.”

•“Streamline your calendar and put a permanent ‘Do Not Talk To Me’ block after board meetings.”

•“Triage your inbox so your sister, your dry cleaner, and your Series A lead investor (extra points if call them out by name) aren’t all sitting next to each other.”

This is what we call executive foreplay. You’re not just a calendar janitor — you’re showing them what it’s like to be handled.

Even if your ideas aren’t perfect, you’ve already separated yourself from the sea of resume-robot candidates repeating “I’m a team player with strong communication skills” like they’re trying to summon Satan.

You’re not just applying. You’re auditioning for the role of right hand, chaos wrangler, and the only person in their life with functioning executive function.

Do less begging. Do more previewing.

You’re welcome.

🗞 I Am Literally Begging ChatGPT To Take My Job!

To further the menty B I was having on my sailing trip I read an article about the CEO of Fiverr's take on what AI is going to do to the workforce. Click the pic below to read the full thing. 

Let's be real... Robots don’t know when to fake-laugh at a board member’s joke — but you do, and that’s priceless.

AI won’t replace you. But the EA who walks into the interview already using ChatGPT to draft investor decks, prep board meetings, and re-write her boss’s passive agressive emails? She absolutely will.

In your next interview, use this cheat sheet to drop a few lines that’ll make you look like an AI-native ops weapon:

1.“I summarize meetings instantly with AI, complete with TL;DRs and action items.”

2.“I use ChatGPT to draft tricky emails that say no… politely.”

3.“I’ve trained AI on my exec’s calendar style so I can pre-filter chaos.”

4.“I turn their brain dumps into LinkedIn content and team updates.”

5.“Travel plans? I use AI to spit out branded itineraries in under 3 minutes.”

6.“I document recurring tasks into SOPs as I go — AI helps format everything.”

7.“I feed messy notes into AI and get clean slides, briefs, or dashboards out.”

8.“Before big events, I use AI to run a risk pre-mortem — saves my ass every time.”

9.“Thank-you notes in their voice? AI can sound more like them than they do.”

10.“I prep pre-meeting intel on attendees — bios, vibe checks, red flags.”

So yeah, fine — take the Fiverr CEO’s advice. Learn the tools. Then walk into that interview and make it clear: you don’t just support the exec, you scale them.

Stuck in your job search? Not sure how to handle a tricky interview question or navigate the hiring process? Submit your question anonymously, and I’ll answer it in an upcoming newsletter—no names, no judgment, just real advice from a recruiter who knows the game.

📅 See you next time!

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