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
Presidents Club

The President's Club Paradox: How a Free Trip Cost Millions Until It Didn’t

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Learn

The Ghost Economy: How Unredeemed Points Became the World’s Most Profitable Liability

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Learn

The Miles Multiplier Myth: Why “Double Points” Isn’t Always Double Value

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Learn

Points & Taxation: What the IRS Doesn’t Tell You About Your Miles

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Learn

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

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DearOhad

Weekend Edition / Dear Ohad #33

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Strategy Saturday

Your Strike Window: The 48-Hour Premium Award Release

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Learn

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

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Learn

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

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Learn

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

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Learn

Amex Membership Rewards: The Power Game That Never Sleeps

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Learn

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

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DearOhad

Weekend Edition / Dear Ohad #32

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Strategy Saturday

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

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Learn

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

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Learn

The 7 Deadly Sins of Points & Miles Management

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Return

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

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Burn

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

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Learn

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

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DearOhad

Weekend Edition / Dear Ohad #31

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