⚙️ Ops Playbook #89

How Creating Virtual Debates Transforms AI from a Magic 8-Ball into Your Executive Team

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⚙️ Hi Operator,

I might’ve stumbled upon a business worth millions… by complete accident.

While I was busy planning community features and template libraries, something unexpected was happening in the background.

Turns out, when you gather 30,000+ operators who actually know how to scale companies without breaking them, you've built the world's most valuable talent network – by accident.

Here's what happened: For the past few months, I've been quietly connecting people behind the scenes.

On one side: Bottleneck readers hunting for roles worthy of their expertise.

On the other: Founders willing to pay anything for operators who can execute from day one.

No AI matching bs. No corporate-speak job listings. Just direct matches between exceptional operators and roles where they can actually move the needle.

The results speak for themselves: Companies are hiring people they'd never find on LinkedIn. Operators are landing roles with actual authority and equity that matters.

So I'm making it official: This back-channel experiment is becoming a core service of The Bottleneck – but staying exclusive. We're connecting the best operators with companies that understand the difference between execution and management.

Below are 17 operational roles where you'll have real impact. No "Chief Happiness Officer" roles here – just positions where you'll build and own critical parts of growing businesses.

And yes, the resource library and community are still in the works.

But I'd be an idiot not to double down on something that's already creating massive value for everyone involved.

- Rameel 

P.S If you are hiring, just respond to this email! I bet I have a great fit 🙂 

PRESENTED BY TRAINUAL
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Jobs, jobs, and more jobs

Here are 17 operational roles you won't find anywhere else:

  1. Technical Program Manager @ AI no code platform (Remote / $190K)

  2. HubSpot CRM Engineer @ AI Video Platform (Remote / $200K)

  3. Customer Success Manager @ Company Shutdown Startup (NYC / $120K)

  4. Founding Deployment Strategist @ AI Dispatching Platform (NYC / $180K)

  5. Founding Operations @ AI Social Platform (SF / $120K)

  6. Founding Agent Manager @ AI Support Platform (SF / $150K)

  7. Head of Tax @ Company Shutdown Startup (NYC / $275K)

  8. Operations Lead - Recruiting Marketplace (SF / $180K)

  9. Founding AI Deployment Lead - Healthcare AI Platform (NYC / $140K)

  10. Chief of Staff - AI Healthcare Delivery Platform (SF / $180K)

  11. Sr. Demand Generation Manager - B2B Revenue Analytics (SF / $210K)

  12. Customer Success Manager - Bookkeeping SaaS (Remote / $100K)

  13. Forward Deployed Strategist - AI Process Automation (SF / $220K)

  14. Business Operations Analyst - AI Banking Platform (SF / $120K)

  15. Deployment Strategist, Utilities - Data Solutions (NYC / $170K)

  16. Strategic Projects Lead - Recruiting Marketplace (SF / $150K)

  17. Deployment Strategist - AI Conversational Platform (SF / $230K)

P.S. Searching for your next role? Fill this out, and we’ll intro you to the best companies in the world

Make AI Fight Itself

Insight from Sourcery

Last month, I was stuck on a business decision that had been giving me headaches for weeks. In desperation, I tried something unusual: I made AI argue with itself. What happened next changed how I use these tools entirely.

Think about how we make decisions in real life. You grab coffee with a colleague who challenges your thinking. You call your mentor who sees angles you missed. You debate with your business partner until you find the right answer.

I've started using AI the same way - not as a magic answer machine, but as a way to explore different viewpoints on tough questions.

Here's the problem with how most people use AI: they treat it like a magic 8-ball. Ask a question, get an answer. But asking AI for a single response is like only talking to your most agreeable friend - you'll get an answer, but probably not the best one.

So I started experimenting with something different: treating AI like a panel discussion. Instead of asking "what should I do?", I create scenarios where different perspectives clash and build on each other.

Here's an example prompt I used recently:

Imagine you're three experts - a Finance Director obsessed with the bottom line, an Operations Manager who lives and breathes efficiency, and an HR Lead who champions workplace culture. I need your help evaluating our hybrid work policy. Challenge each other's blind spots and don't hold back. Once you've debated it out, what's your collective recommendation?"

What happened shocked me. The Finance Director argued for immediate monetization, pushing for premium features in the first email to maximize revenue. The Product Manager pushed back, worried about overwhelming new users and hurting activation rates.

Marketing jumped in with a compromise: a strategic free trial of premium features during onboarding, followed by a timely upgrade prompt. The debate forced each perspective to defend its position with conversion data and user behavior patterns.

More importantly, it revealed the critical balance between user experience and revenue that I'd been missing.

This approach works best for:

  • Complex decisions where multiple factors compete

  • Situations where you need to pressure-test assumptions

  • Problems that feel stuck because you're missing something

Look, this isn't some magic trick for simple questions or fact-checking. But for those thorny problems that keep you up at night? The ones where every solution feels wrong? Try making AI argue with itself. You might just find the clarity you've been missing.

Because sometimes the best answers don't come from a single source of truth.

They emerge from the clash of competing ideas - even if those ideas are coming from the same AI.

P.S. Let me know what you thought of today’s piece! Reply to this email or tell me here!

Whenever you're ready, there are 3 ways we can help you:

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We have a growing audience of 30,000+ operators from top companies like Apple, Meta, Stripe, Faire, and Google. Apply to feature your business in front of The Bottleneck readers.

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