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Prospectingwork — The Rick Rubin Approach to Cold Outreach (95% Work, 5% Ask)

A positioning diagnostic — done for free, unsolicited, sent as a gift. One soft CTA at the very end. If it is sharp, they reply. If it isn't, no follow-up would have saved it.

License: MIT Claude Code Strategy Sprints

Who this is for:

  • B2B founders, consultants, and account executives who are tired of spam-tier cold emails
  • Agencies selling $30K-$500K engagements who need the first touch to do the work of a 30-minute call
  • Sales teams that want a repeatable positioning-diagnostic motion their AEs can actually run
  • Anyone who has heard "stop pitching and start helping" but never been shown the exact format

What happens when you send one

You research a prospect's website, find three positioning gaps, write proposed new copy for each one, and email it to the founder. One soft ask at the end: "30 minutes.. for free.. pick your best time."

Early results across 50+ diagnostics sent to Series A+ founders:

Metric Number
Avg reply rate [tracking — update after 30 sends]
Replies → calls [tracking]
Calls → clients [tracking]
Avg time to reply [tracking]

If you're using this skill, track your numbers and update this table. The method is only as good as its proof.


The email format

Subject: their first name. lowercase. nothing else.

Opening: {Name}, {three contradictions from their site}. Here is my proposal: — straight into the work. No emoji in opener.

Three findings (⚡️⚡️🐯). Each ends with "What if instead →" and proposed copy they could paste tomorrow. Finding 3 goes deeper — acquisitions, dollar amounts, market window.

One closing question in italic. The kind that haunts.

CTA: "I'd love to put another 30 minutes into strategizing with you. for free. Pick your best time:" + Calendly link.

Sign-off: name / CEO title + URL / author line.

Length: 250-350 words. Dense, visual, sharp.


Real example #1: Celonis (gold standard — sent 2026-03-24)

Subject: bastian

Bastian, your headline says "AI layer." Your body copy says "process mining." Your CTA says "Try for free." Three identities, one page. Here is my proposal: ⚡️ You buried the best frame on the internet "The missing layer in your AI stack" — that's a category-defining statement. It repositions Celonis from a process mining tool (shrinking category, competitors getting acquired by SAP, Microsoft, IBM) to an AI infrastructure layer (massive growing market). But below that headline.. the page reverts to process mining language. Supply chain optimization. Working capital. Service levels. Those are legitimate use cases, but they belong to the old positioning.

What if instead → "Enterprise AI fails when it doesn't understand how your business actually runs. We fix that." Problem-first. Conversational. Creates urgency. The current headline is a thesis statement. This one is a door.

⚡️ "Try for free" is the wrong CTA for your buyer Your customers are Mercedes-Benz, enterprise banking, automotive. A VP of Digital Transformation at Mercedes doesn't want to "try for free" — they want to see proof at their scale. "Try for free" signals self-serve mid-market. It belongs to the process mining era, when you were competing with tools. You're competing with platforms now.

What if instead → "See how Mercedes-Benz uses Process Intelligence to run AI across 30+ factories." Social proof. Specificity. Aspiration. Enterprise buyers buy outcomes, not free trials.

🐯 The move nobody sees → you're the last independent player Signavio → acquired by SAP for $1.2B. Minit → acquired by Microsoft. Myinvenio → acquired by IBM. Every major competitor got absorbed into a larger platform story. Celonis is the last standalone process intelligence company. Your independence is either a vulnerability or a weapon.. depending on how you frame it. Right now the website doesn't frame it at all.

What if instead → "Every other process mining company got acquired. We stayed independent. Here's why that matters for your data." Independence means vendor-neutral. It means your process data doesn't get locked into one cloud ecosystem. That's a story SAP Signavio literally cannot tell. You have maybe 12-18 months before the acquirers start claiming "AI infrastructure layer" too.

Here's the question I can't shake: when SAP tells your prospects "we have process mining built in now".. what's the one sentence that makes them pause and say "but that's not the same thing"?

I'd love to put another 30 minutes into strategizing with you. for free. Pick your best time: https://calendly.com/simonseverino/coffee-with-simon

Simon Severino CEO, Strategy Sprints™ → strategysprints.com Author of Strategy Sprints (Kogan Page) and Time Freedom with Jay Abraham

Why this works: Opens with three contradictions on their own page. "Here is my proposal:" signals generosity. Finding 3 goes deep — names acquisitions, dollar amounts, market window. CTA is soft and generous at the very end.


Real example #2: Gorgias (Opener C — The Straight Shot)

Subject: romain

Romain,

Three positioning gaps in Gorgias's website. One of them is hiding your best edge from every visitor who scrolls past the hero ⚡️ You're the only support platform that generates revenue — but you don't say it Your headline: "The Conversational AI platform for Ecommerce." Every chatbot vendor says conversational AI. But Zendesk is support. Intercom is support + some marketing. Gorgias is support that sells. That's your edge.. and it's buried.

What if instead → "The only support platform that pays for itself." Falsifiable claim. Competitors can't match it.

⚡️ Your CTA is invisible "Start free trial" — every SaaS site on earth. A VP of Ecommerce scanning your page doesn't feel urgency, doesn't feel specificity. You're asking them to try. You should be asking them to see.

What if instead → "See how support becomes revenue." Outcome-driven. Pre-qualifies the right buyer.

🐯 Two products hiding inside one brand $10/mo Starter (50 tickets) to $750/mo Advanced (5,000 tickets). That's a 75x spread. The $10 customer and the $750 customer are not the same person.. but your website speaks to both with the same page. The small store sees "start free trial." The mid-market buyer needs ROI math and case studies.. and gets the same page as the $10 plan.

What if instead → Split the narrative. One path: "Getting started." One path: "Scaling revenue through support." Let each buyer see themselves.

Here's the question I can't shake: which customer is Gorgias really for — the $10/mo Shopify starter or the $750/mo brand? Because right now the website can't decide.. and neither can the visitor.

— Simon Severino CEO, Strategy Sprints™ → strategysprints.com Author of Strategy Sprints and Time Freedom with Jay Abraham

Why this works: Straight shot opener — no clever hook needed when the findings are sharp enough. The 75x pricing spread is a number that makes the blind spot undeniable.


Real example #3: Gong (Opener B — The Research Proof)

Subject: amit

Amit,

Your State of Revenue AI report says teams using Gong generate 77% more revenue per rep. Your homepage doesn't. Here's what I'd fix ⚡️ Your best proof point is hiding behind a PDF download 77% more revenue per rep. That's your strongest number. But it lives in a gated report, not above the fold. Your homepage leads with "The #1 AI operating system for Revenue Teams" — a claim. The 77% is a proof. Claims get skipped. Proof stops the scroll.

What if instead → "Every customer interaction. Captured, understood, and turned into revenue." Names the outcome. Feels like an OS. Doesn't need a superlative.

⚡️ Six personas, one homepage CRO, RevOps, Sales, Customer Success, Enablement, Technology. Each one scrolls the same page hoping to find their story. The CRO evaluating Gong and the enablement manager evaluating Gong have different buying criteria.. but see the same funnel.

What if instead → Split the entry. "I'm a CRO" → pipeline story. "I run enablement" → ramp story. Two clicks. Not one generic page.

🐯 The move nobody is making → own the number "Revenue AI OS" is a category you're trying to create. But categories take years. The 77% number is available NOW. No competitor can claim it. "Gong teams sell 77% more" is a position.. "Revenue AI OS" is an aspiration.

What if instead → Lead every page, every ad, every pitch with "77% more revenue per rep." Own the number. Let the category follow.

Here's the question I can't shake: if "Revenue AI OS" disappeared from your site tomorrow and was replaced with "77% more revenue per rep".. would you lose a single deal?

— Simon Severino CEO, Strategy Sprints™ → strategysprints.com Author of Strategy Sprints and Time Freedom with Jay Abraham

Why this works: Opener B — uses their own published data against their homepage. The 77% number is too good to bury, and pointing that out is a gift, not a critique.


The three openers

Pick the one that fits your research. Default to A (it works most often).

Opener A — The Provocative Number (default)

Your homepage subheadline is 42 words long. Gong's is 6. Here's what I'd change Best when you found a specific metric, word count, or competitor comparison. Two numbers, one contrast — impossible not to keep reading.

Opener B — The Founder Quote / Research Proof

You told an interviewer: "one very simple wedge." Your website tells a different story. I wrote down what I'd fix Best when the founder is active on content or has published data. Quoting them back to themselves proves research depth.

Opener C — The Straight Shot

Three positioning gaps in {Company}'s website. One of them is costing you every visitor who leaves in under 8 seconds Best when you don't have a strong quote or number. "Costing you" leads with self-interest. Works for anyone.


The 13 rules

  1. No pitch. Zero. No mention of services, coaching, or anything that smells like selling
  2. CTA at the end. "I'd love to put another 30 minutes into strategizing with you. for free." + Calendly coffee link
  3. No compliments. Open with the work, not "I love what you're building"
  4. Be specific enough to be wrong. That's why it works
  5. Use their language. Quote their own words. Name their competitors
  6. Every finding includes proposed new copy. "What if instead →" with text they can paste
  7. Finding 1 = their hidden strength. Lead with what's working
  8. Finding 2 = the gap that's costing them. Numbers, word counts, comparisons
  9. Finding 3 = the move nobody is making. Name a category that doesn't exist yet
  10. End with one sharp question. The kind that keeps them up at night
  11. Use .. for pauses, for transitions, ⚡️ for findings 1-2, 🐯 for finding 3. No other emojis
  12. Write like a human. Short fragments. White space. Imperfect punctuation
  13. 200-300 words. Dense, visual, sharp. Not a report — a diagnosis

When they reply

The diagnostic has a soft CTA at the end. When they reply:

  1. Acknowledge what they said. Don't pivot to a harder pitch. Respond to their actual words.
  2. Confirm the 30-minute call. The CTA already offered it. Just confirm.
  3. That's it. The diagnostic earned the trust. The call earns the relationship. The relationship earns the work.

Installation

Claude Code

cp prospectingwork.md ~/.claude/commands/prospectingwork.md

Then run:

/prospectingwork {company name}

Manual

Follow the 5-lens framework in prospectingwork.md. Research → diagnose → prescribe → send.


The philosophy

Rick Rubin doesn't add production to make a song better. He strips everything away until the song can't hide.

The diagnosis IS the pitch. The specificity IS the trust signal. The absence of an ask IS the differentiator.

Everyone sends promises. Nobody sends the actual work, done, for free, before being asked.


FAQ

Does this really work at scale? It works at single-sender scale (one human, 5-10 diagnostics a week). Above that it degrades fast — the specificity is the entire asset. Send it broad and it reads like template outreach. Keep it narrow and it reads like a gift.

How long does one take to write? Research: 45 min. Writing: 45 min. Total: ~90 min per prospect at the start. After 20 reps it compresses to 45-60 min total.

Can AI do this autonomously? AI can draft the skeleton. The specificity that makes it land — the contradiction spotted, the competitor named, the acquisition referenced — requires human judgment on top. Treat AI as a research accelerator, not a replacement.

What reply rates should I expect? Early private data across 50+ sends suggests a 15-30% reply rate for well-researched Series A+ targets. Below 15% = not specific enough. Above 30% = probably means your sample is too warm to call it cold.

What do I do when they don't reply? Nothing. No follow-up. The philosophy is that a good diagnostic carries its own weight. A follow-up email invalidates the gift. Move to the next prospect.

Can I modify this for SMB targets instead of Series A+? Yes. Scale the findings to their scale. Instead of naming acquisitions, name their specific customers or regions. The format scales; the depth is what shifts.


Related search terms

Rick Rubin cold email · positioning diagnostic · value-first outreach · anti-prospecting · B2B cold email · cold email that works · account executive cold outreach · consultative selling · first-touch sales email · founder-led sales · specific cold email · personalized cold email · gift email · Celonis positioning · Gorgias positioning · Series A cold outreach · agency new business · Claude Code prospecting · AI cold email · Strategy Sprints methodology


About

Built by Simon Severino, founder of Strategy Sprints. Author of Strategy Sprints (Kogan Page, 9 languages) and Time Freedom with Jay Abraham. Added over $2 billion in sales to B2B clients in finance, software, and consulting. Used daily inside Sprint Club by 254+ founders across 72 countries.

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MIT. Steal the method. Send gifts, not pitches.

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Positioning diagnostic prospecting — the Rick Rubin approach to cold outreach. No pitch. No CTA. Just the work.

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