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Sell Bigger, Win Smarter

Close complex, high-value deals with strategy and conviction

For founders moving upmarket: selling to enterprise clients, dealing with several decision-makers, or selling high-priced offers where relationships and strategy matter as much as tactics. You will learn to control long sales cycles, challenge what buyers assume, and win deals your competitors miss.

9 books, 2h 35m
Explore the first book →← All paths for this goal
Sell Bigger, Win Smarter cover
Sell Bigger, Win Smarter cover
Sell Bigger, Win Smarter cover

Your reading order

9 books
  1. 1

    The Challenger Sale

    Matthew Dixon

    The rules change when you sell big. Dixon's research breaks the myth that building relationships alone wins large deals. It shows that challenging your customer's thinking is what actually drives revenue.

  2. 2

    Elite Sales Strategies

    Anthony Iannarino

    Building on the Challenger mindset, Iannarino's One-Up framework shows you how to know so much that clients seek your guidance instead of just comparing your price.

  3. 3

    Complex deals have several decision-makers, and most founders only talk to one. Miller's Strategic Selling maps every key role in a buying organization so no deal falls apart because of a hidden blocker.

  4. 4

    Now add a discipline for qualifying deals. Page's RADAR framework replaces hope-based selling with a strict process for spotting winnable opportunities and walking away from the ones you can't win.

  5. 5

    With strategy set, master the conversation itself. Peterson's approach uses stories, visuals and psychological triggers to move buyers past indecision and win high-stakes deals at the table.

  6. 6

    Pitch Anything

    Oren Klaff

    Next comes the moment that matters most: the pitch. Klaff's brain-biology framework shows you how to control the frame, own the room, and make your offer feel inevitable rather than negotiable.

  7. 7

    Sales EQ

    Jeb Blount

    Even the best strategy fails if emotions derail the deal. Blount's Sales EQ teaches you to manage your own emotions while reading and influencing the hidden triggers that drive your buyer.

  8. 8

    The JOLT Effect

    Matthew Dixon

    The last enemy of big deals is not objection but indecision. Dixon's JOLT framework gives you specific moves to overcome buyer paralysis and close deals that would otherwise stall with no decision.

  9. 9

    Once you're winning at this level, stop giving away free pitches. Enns's manifesto shows high-value service providers how to position themselves as the expert, so clients come to you on your terms.

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