Jon Caldwell
@JonCaldwell_
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Helping B2B tech & services founders grow | 1x exit | $23M+ in sales of software, services, hardware & cos
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Joined November 2022
Want the full guide on how you can turn a sales call into 1 month of content? Check this out:
gamma.app
Video Walkthrough: Founders: Turn ONE Sales Call Into 30 Days of B2B Content (AI Framework) Typical Scenario You just had an amazing conversation with a prospect. You explained your solution perfec...
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A solution that keeps your authenticity: - Feed AI your actual transcripts and voice samples - Provide good and bad examples of tone - Give thorough context: your ICP, your mission, even your casual phrases AI only amplifies your voice if you give it the right examples.
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You talk with passion on calls. You handle objections like a pro. Then you sit down to create content... and it feels flat. Why the drop-off? - Outsourcing without proper guidelines - No “Founder Voice” document - Generic prompts with no context
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Want the full guide on how you can turn a sales call into 1 month of content? Check this out:
gamma.app
Video Walkthrough: Founders: Turn ONE Sales Call Into 30 Days of B2B Content (AI Framework) Typical Scenario You just had an amazing conversation with a prospect. You explained your solution perfec...
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Your best insights aren't in blog research. They're in yesterday's client meeting.
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Why most outsourced B2B content fails: It's written by people who've never: • Run your sales calls • Solved your problems • Worked with your clients • Built your solutions Stop trying to create content. Start documenting expertise.
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Want the full guide on how you can turn a sales call into 1 month of content? Check this out:
gamma.app
Video Walkthrough: Founders: Turn ONE Sales Call Into 30 Days of B2B Content (AI Framework) Typical Scenario You just had an amazing conversation with a prospect. You explained your solution perfec...
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(Not what you do - what it means for them) Step 4: Find who cares most about that value (Your true market) Step 5: Position to be their clear best choice (Not the best overall - the best for them) Most founders do this backwards. They start with features and work up.
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Found an interesting framework for startup positioning, from April Dunford. Step 1: What happens if you disappeared tomorrow? (This reveals your true competition) Step 2: List what you have that they don't (Not features - real differences) Step 3: Map those to customer value
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- Which explanations got the best response? - What objections did you handle well? That's your content strategy right there. No need to manufacture insights. Just capture and share what's already working.
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Most B2B content fails for a simple reason: It's created backwards. Companies start with: "We need to post something", instead of "What do our prospects actually need to know?" Look at your last 5 sales calls (you better be recording these): - What questions kept coming up?
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Not the subject line. Not the sequence. It's the impact. Campaign A pitched strategic acquisitions. (Impacts every department) Campaign B pitched a point solution. (Impacts 1-3 people) The bigger the impact, the better the response higher up the org.
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Some cold email math that might surprise you: Campaign A: 700 leads → 41 positive replies (17:1 ratio) Campaign B: 6,000 leads → 4 positive replies (1,500:1 ratio) Same target persona. Same company size. 88x difference in performance. The key? Not the copy.
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Everything else follows. Start with these questions: • Who loves your product most? • What would they use if you disappeared? • What unique value do you provide them? • Which segment of the market values this most? Narrow until you can dominate.
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Product decisions Marketing focus Sales strategy Partnership choices Integration priorities Fix your positioning first.
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Your product roadmap is broken. Your marketing is scattered. Your sales team is struggling. Why? Positioning. It sits upstream from everything:
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