The Operator

Ohad Sternberg

5M+ miles flown. 70 countries. 629 programs tracked. The person friends text at 11pm about whether to transfer to Aeroplan.

Ohad Sternberg
Ohad Sternberg
Essays by author
Learn

The Chase Sapphire Countdown: Everything You Must Do Before the "Reserve" Revamp on Oct 26

DearOhad

Weekend Edition / Dear Ohad...

Strategy Saturday

Your Strike Window: The 48-Hour Premium Award Release

Learn

CapitalOne Miles: The End of Easy Value (Q4-2025 Field Manual)

Learn

Citi "ThankYou" in Q4-2025: When "Strata" Tries to Reforge Loyalty

Learn

Bilt Rewards in Q4-2025: How Renting Became a Loyalty Asset

Learn

Amex Membership Rewards: The Power Game That Never Sleeps

Learn

Chase Ultimate Rewards: The Loyalty Market You Didn’t See Coming

DearOhad

Weekend Edition / Dear Ohad...

Strategy Saturday

The Spend Stack: How to Build a Self-Funding Business

Learn

The CFO of Miles: How Smart Businesses Appoint a Chief Points Officer

Learn

The 7 Deadly Sins of Points & Miles Management

Return

The Points Illusion: Why Earning Isn’t Winning Until You Redeem Right

Burn

Your Most Expensive Employee Is You: Why CEOs Should Never Book Their Own Award Travel

Learn

Earning Points for Kids: How to Give Your Children a Head Start in Travel Rewards

DearOhad

Weekend Edition / Dear Ohad...

Strategy Saturday

The Status Mirage: Why Business Owners Chase Airline Status the Wrong Way, Burning Cash Instead of Optimizing Points (And How to Flip the Script)

Learn

The Bankruptcy Bonus: Do Miles Survive When Your Finances Don’t?

Learn

The Divorce Dividend: Who Gets the Miles When Love Crashes and Burns

Earn

The Real Value of Your Airline Miles in Q4-2025 | Spoiler: Some Are Basically Monopoly Money

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