Strategy Sprints — Simon Severino

How well does your offer travel

Mon, 21 Sep 2026 07:48:58 +0000

The yes does not happen in the room with you anymore.

It happens on a call you are not invited to, between three or four people, one of whom has to explain your offer from memory.

🐯 So the real question is not how well you present. It is how well you travel.

That is a positioning problem, and it is brutal, because the version of you that gets repeated internally is always shorter, flatter and more expensive-sounding than the version you delivered.

🐬 The fix is not a better deck. It is Step 5 Deliverables, done properly.

Step 5 is where the buyer defines success in their own words. Not your words. Theirs. "Talk to me about what you want to be true 10 days from now."

Then you write down exactly what they said. Their phrasing, their metric, their deadline. No polish, no reframe into your language.

🌴 That sentence goes into the Step 8 Statement of Work verbatim.

Now the document doing the rounds internally is not your marketing. It is their own sentence, handed back to them. Nobody argues with their own words.

That is the difference between a champion who has to sell you and a champion who only has to forward you.

Before Strategy Sprints, this came out of coaching 2,000+ teams on selling and negotiation, including at Google, BMW and Airbus. Those rooms have eight people in them. It taught me that the deals that close are the ones that survive the conversation you are not in.

🐯 If you want to think out loud about where your offer loses shape on the way through a company, grab 30 minutes: calendly.com/simonseverino/coffee-with-simon

Your hand moves toward the discount

Mon, 21 Sep 2026 07:48:57 +0000

A buyer hesitates. Your hand moves toward the discount.

2026 made that reflex much stronger. Longer cycles, more people reviewing, more scrutiny before anyone says yes. Cutting price feels like the one lever you fully control.

🐬 It is the one lever that removes your control.

A discount answers a question the buyer never asked. They did not say "too expensive." They said nothing, or they said "let me check internally." Price was your guess at their silence.

🐯 Here is the sequencing that replaces it.

Step 4 is Cost of Inaction. Not your pitch about it. Theirs. "If this stays exactly as it is for the next twelve months, what does that cost you?" Then stop talking and let them do the math out loud. The number they say is the number your price gets compared against, forever.

Step 6 is Investment, and it has an order: time, then people, then money. In that order, always.

🌴 Money last is not a trick to hide the price. It is the only position where the price means anything. A founder who has just told you what standing still costs, and has already agreed to the hours and the people, is evaluating a trade. A founder who hears the number first is evaluating an expense.

Same deal. Same price. Two completely different conversations.

Founders who run the steps in order average a 25% higher win rate after 90 days, on deals that were already sitting in the pipeline. Not new leads. The ones already there.

🐬 If you want to look at where your own sequence breaks, the 90-day fit check is here: calendly.com/strategysprint/discovery-call

The deal dies in the thread you were never in

Mon, 21 Sep 2026 07:48:52 +0000

Deals are not dying at the close in 2026.

They die about three weeks after the first call, in a thread you were never in.

🐬 The reflex when that happens is to send more. More sequences, more touches, more "just bumping this to the top of your inbox."

That reflex is the thing that costs you the deal.

Chasing hands the steering wheel to the buyer. And a buyer holding the wheel is not evaluating you. They are deferring you.

🐯 Low win rates are almost never a volume problem. They are an order problem. Right moves, wrong sequence.

Step 2 of the Repeatable Sale is Frustration. It comes before anything about what you would deliver. The literal wording:

"What have you already tried to fix this, and what happened?"

Then say nothing.

You get one of two things. Either a list of everything that failed before you showed up, which is the real brief. Or silence, which tells you the problem is not actually costing them anything yet.

🌴 Skip that and jump to Step 5 Deliverables, and you end up pitching a solution to a problem nobody has priced out. That is the deal that goes quiet in week three.

The ordering is the whole game. It is the pattern behind 500+ founders in 40 countries and over $2 billion in additional client revenue: same steps, in sequence, every time.

So, the one worth arguing about..

What is the last question you ask before a deal goes quiet on you?

The Algorithm - DM PAUSE

Mon, 07 Sep 2026 11:38:27 +0000

In the last planning meeting, someone said let's get AI to handle this.

Nobody asked why the process needs to exist in its current form. They just voted to make it faster.

That's how a workflow nobody can defend anymore turns into a workflow nobody can touch anymore. Once it's automated, ripping it back out costs ten times what building it did.

I run every automation idea through 5 steps before it gets built: question the requirement, delete what doesn't survive, simplify what's left, speed it up, then automate, dead last.

DM me PAUSE and I'll send it over.

36 Sales Gaps Checklist: score your deal

Mon, 07 Sep 2026 11:05:00 +0000

There are 36 specific reasons a B2B deal stalls before it closes. Which ones are live on your current deal?

We built a free checklist, the same one we run internally before every proposal. Client-side, team-side, contract-side. Takes about 4 minutes, no email trickery, just answer honestly.

Score your deal: www.strategysprints.com/36-sales-gaps

ClaudeSkills-SprintClub: 25 skills open-sourced

Mon, 07 Sep 2026 11:04:57 +0000

25 free Claude Code skills. Every stage of a B2B deal.

Prospecting, pipeline management, closing, negotiation, enterprise deal navigation: we turned the entire Strategy Sprints sales system into skills anyone can run in Claude Code.

No paywall on the framework itself. Open-source, MIT-licensed, yours to fork.

Grab it: https://github.com/SimonTheSalesBooster/ClaudeSkills-SprintClub

The Algorithm - the optimize trap

Mon, 07 Sep 2026 10:58:44 +0000

Somewhere on your team there's a dashboard that's been rebuilt three times this year.

New filters. Better colors. A cleaner export button. Every version ships as a win.

Nobody has asked: does anyone actually act on what this tracks. If the answer is no, you've spent months polishing something that should have been deleted in week one.

The most common mistake a smart team makes is optimizing a thing that should not exist.

Comment SHINY if you've got a dashboard, report, or tracker like this right now.

The 5-step method that catches this before you polish it, free: github.com/SimonTheSalesBooster/the-algorithm

The Algorithm - automating the wrong thing

Mon, 07 Sep 2026 10:58:41 +0000

Right now, someone on your team is building an AI agent.

It's wrapped around a workflow nobody has questioned in years. An approval chain. A report format. A hand-off between two people who don't even need to be in the loop anymore.

Nobody asked if the process should exist first. They just made it faster.

Ship it, and the same broken workflow just runs quicker. Now there's software holding it in place, and good luck ever pulling that back out.

Comment PAUSE if you or someone on your team is mid-build on an agent for a process that should have been deleted first.

The 5 steps to run before you build, free: github.com/SimonTheSalesBooster/the-algorithm

The Algorithm - the under-deletion tell

Mon, 07 Sep 2026 10:58:38 +0000

Elon Musk's rule for cutting anything: if you never have to add back at least 10% of what you deleted, you weren't aggressive enough.

Most people cut the easy 20%. The safe stuff. The stuff nobody would miss anyway. Then they stop, call it done, and never touch the parts that were actually load-bearing.

Real cutting means occasionally guessing wrong. You delete something, someone screams, you put it back. That's proof the knife was sharp enough.

Comment SAFE if you've cut processes before and never once had to bring anything back. That usually means the cuts were never that aggressive to begin with.

Musk's full 5-step method, free: github.com/SimonTheSalesBooster/the-algorithm

The Algorithm - the unowned requirement

Mon, 07 Sep 2026 10:58:34 +0000

There's a meeting on your calendar right now that nobody remembers requesting.

An approval step. A recurring report. A weekly sync that has run for two years straight.

Ask five people why it exists and you get five different guesses. Ask who owns the requirement, the actual name of a person who could kill it, and the room goes quiet.

That silence is the tell. No named owner means it survives by default, not by merit.

Comment OWNER if you've got one of these running right now and you genuinely don't know whose call it was.

The 5-step method that catches these before they multiply, free: github.com/SimonTheSalesBooster/the-algorithm

36 Sales Gaps Toolkit: builder angle

Mon, 07 Sep 2026 10:45:09 +0000

Open-sourced our internal deal-diagnostic framework today.

36 Sales Gaps: every reason a B2B deal stalls, mapped in three categories, each with an exact fix. It's what we run internally before every proposal and every deal review.

Turned it into 13 Claude Code skills. /gap-scan takes a deal and tells you exactly which of the 36 are live.

Free, MIT-licensed, on GitHub: https://github.com/SimonTheSalesBooster/36-sales-gaps-toolkit

36 Sales Gaps Toolkit: contrarian angle

Mon, 07 Sep 2026 10:45:07 +0000

It's never "budget." It's never "timing." Those are just the two reasons buyers give you.

We mapped the 36 actual reasons a B2B deal dies: a stakeholder nobody mapped, a decision-maker who never saw the proposal, a margin that quietly went negative, an SOW that only ever lived in someone's memory.

13 free Claude Code skills, one for each type of gap. Paste in your stuck deal, get the real reason back: https://github.com/SimonTheSalesBooster/36-sales-gaps-toolkit

36 Sales Gaps Toolkit: team-gap angle

Mon, 07 Sep 2026 10:45:06 +0000

Your team is not the problem. Except for 7 specific ways it might be.

We mapped 36 reasons B2B deals stall. Client-side, contract-side, and 7 that live entirely on your own team. Not "didn't try hard enough" reasons. Specific ones: not sure why working with us is urgent right now, delivery capacity never confirmed, pulled into an RFP instead of a real conversation.

Free Claude Code skill audits your team against all 7 before you propose: https://github.com/SimonTheSalesBooster/36-sales-gaps-toolkit

Optimize nothing that shouldn't exist

Mon, 07 Sep 2026 10:43:10 +0000

The most common error of a smart engineer is to optimize a thing that should not exist. Question it. Delete it. Only then simplify, speed up, and automate what's left.

The Algorithm - fork it

Mon, 07 Sep 2026 10:43:04 +0000

We open-sourced the five-step framework we run before we let ourselves build anything new. Question every requirement. Delete what has no named owner. Simplify what survives. Speed it up. Automate dead last. It's a Claude Code skill. Paste in your process, your tech stack, or that half-built automation nobody's finished, and it tells you what to cut before you add anything else. Free and open-source. Fork it, run it on your own team. github.com/SimonTheSalesBooster/the-algorithm

AI agents on broken processes

Mon, 07 Sep 2026 10:42:56 +0000

Everyone is racing to build an AI agent this month. Almost nobody is asking if the process underneath it should exist at all. An agent bolted onto a bloated workflow doesn't fix the workflow. It runs the bloat faster, and now there's software wrapped around it that's much harder to ever pull back out. Before you build the agent: question every step, delete what nobody can name an owner for, simplify what's left. Then speed it up. Automate last, not first. That order is the whole difference between an agent that removes work and one that just industrializes a mess. Free skill, five steps, no infrastructure required to try it: github.com/SimonTheSalesBooster/the-algorithm

Sales processes need a knife

Mon, 07 Sep 2026 10:42:50 +0000

Most sales processes don't need a new tool. They need a knife. Extra approval on the SOW. A CRM field nobody fills in. A forecast call that exists because it always has. Every one of those got added by someone, at some point, for a reason that made sense that week. Nobody ever goes back and asks if it's still earning its place. That's how a 4-step sale quietly turns into a 9-step slog nobody can explain. The 8 Steps of the Repeatable Sale we teach every client used to be twice as long. We questioned every stage, cut the ones that made the seller feel busy instead of moving the buyer forward, and only then built anything to speed it up. Fewer moving parts isn't the compromise. It's the whole method. Before you add another approval or another field, question it first: github.com/SimonTheSalesBooster/the-algorithm

The approval step nobody owns

Mon, 07 Sep 2026 10:42:44 +0000

A team asked me: "can we add an approval step before this goes out, and build a dashboard to track how long approvals take?" Ran it through The Algorithm instead. Question: who owns the requirement that this needs approval? No name, no reason. Just a leftover from when the team was three people. Delete: remove the approval step. Replace it with a standard the sender checks themselves. Simplify: one checklist, three items. Accelerate: sends go out same day now, not whenever the reviewer opens their calendar. Automate: nothing yet. Not until the manual version runs clean for a month. No dashboard needed. The thing it measured should not have existed. github.com/SimonTheSalesBooster/the-algorithm

Delete before you automate

Mon, 07 Sep 2026 10:42:36 +0000

Delete before you automate. Elon Musk drills this into every engineering team at SpaceX, Tesla, and Boring Company (it's in Isaacson's biography). Five steps, always in this order: 1. Question every requirement. No named owner, delete it. 2. Delete the part or process. If you're not adding back 10%, you weren't aggressive enough. 3. Simplify what survives. 4. Speed it up. 5. Automate. Dead last, always. Skip to step 5 first and you just spent real money automating a mistake, faster. We turned it into a free Claude Code skill. Free. Open-source. Grab it: github.com/SimonTheSalesBooster/the-algorithm

36 Sales Gaps Toolkit launch

Mon, 07 Sep 2026 10:33:31 +0000

36 reasons a B2B deal dies before it closes. We mapped every one of them.

If you've ever watched a good deal go quiet and couldn't say exactly why, it's usually not budget and it's not timing. It's something specific and nameable: a stakeholder who never got mapped, a margin that never got checked, an SOW that stayed verbal.

20 of the 36 live on the client's side. 7 on your team's side. 9 buried in the contract.

We turned the full framework into 13 free Claude Code skills. Paste in a stuck deal, get back exactly which gaps are live and the move that closes each one.

Free. Open-source. Grab it: https://github.com/SimonTheSalesBooster/36-sales-gaps-toolkit

8 Steps Repeatable Sale - DM funnel

Wed, 26 Aug 2026 14:59:58 +0000

Every deal that's gone right for the 2,400 people we've coached followed the same 8 steps, in the same order. Every deal that's stalled skipped one. Step 4, for one: "What happens if you do nothing?" Most people skip straight past it and wonder why the deal goes quiet. Skip a step and the deal stalls. Run them in order and the close feels obvious. Most people are still guessing which step they skip. I've never published the one-pager we run internally. Still has the coffee-ring stains from a hundred real calls. All 8 steps, in order. DM me READY and I'll send it over.

Sales isn't the goal

Fri, 17 Jul 2026 16:21:04 +0000

Sales is not something to strive for. It is what happens after you help someone make real progress on a problem they are stuck on. Can I help you solve this. Can we build this together. Can we break through that wall. That is the fun part, and it is the only part that earns you the right to ask for the close. Chase the close first and buyers feel it. Chase the problem first and the close finds you. Clip from my conversation on Doing Business with a Servant's Heart with Steve Ramona.

Dinner with Jesus and Schnitzel

Fri, 17 Jul 2026 16:21:03 +0000

Steve Ramona asked me a question I was not ready for: reserve a table in Vienna, invite three people who shaped your life, then pick the meal. Schnitzel, obviously, we are in Vienna. The harder part was the guest list. I left seats open on purpose. The people who show up uninvited are usually the ones worth having there. Some questions are not about tactics. They are about who belongs at the table once the tactics stop mattering. Full conversation on Doing Business with a Servant's Heart with Steve Ramona, link in comments.

The nicest people close the fewest deals

Fri, 17 Jul 2026 16:21:01 +0000

The nicest people on sales calls close the fewest deals. After 23 years coaching sales conversations, that is the pattern I keep seeing. They listen. They say yes to everything the buyer asks for. The buyer leaves calling them a great resource. Then nothing happens. Service does not mean surrendering control. It means preparing so well that you can lead the conversation toward a decision, not give away an hour of free consulting. The people who actually help buyers are the ones running the call, not agreeing with it. Clip from my conversation on Doing Business with a Servant's Heart with Steve Ramona. Full episode link in comments.

I fired my CRM

Fri, 17 Jul 2026 16:20:59 +0000

Five months ago I stopped opening a CRM. Not because I stopped tracking pipeline. Because I do not have to click through one anymore. I ask one question: who are the three people I need to follow up with today. My AI agent checks every conversation, finds what I promised, drafts the exact offer I owe, and drops it in my Gmail draft folder. I just say send. It coded its own CRM inside Notion in ten minutes. I cancelled Salesforce the same week. 43 agents running my pipeline. 200 dollars a month. That is the entire stack now. If you are still logging activity by hand, you are not behind on AI. You are behind on delegation. Clip from my conversation on Doing Business with a Servant's Heart with Steve Ramona. Full episode link in comments.

sevencritics MCP storefront

Sun, 17 May 2026 05:42:40 +0000

Copy that reads like nobody wrote it. That is the goal. I built a free Claude Code skill. Seven hostile readers tear your draft apart. The skeptic. The CFO. The bored scroller. Each one tries to break it. github.com/SimonTheSalesBooster/sevencritics Run it on your next post.

Tailwind Tuesday repo launch

Sun, 03 May 2026 03:49:15 +0000

Most shoutout posts online get scrolled past. The author picks whoever they met yesterday and the reader can feel the lack of substance. Here is what we have been doing instead. Every Tuesday at 8am Vienna, an agent we built scans the past 28 days of my calendar, my call transcripts, and my coffee bookings. It picks ONE human I have had at least three real touchpoints with that month. Then it checks: have I actually witnessed a superpower, an act of integrity, or a moment of loyalty from this person? If the answer is yes with concrete evidence, it drafts a 5-line shoutout. If the answer is vague, it skips the week. The post celebrates THAT person. Their LinkedIn. Their work. Their ICP. Zero CTA back to me. No mention of my offers. No "DM me to learn more." The whole thing is a gift, or it does not ship. We call it Tailwind Tuesday 🪂 The world has too many promoters and not enough endorsers. So we built the system, ran it for a while, and today we open-sourced it. Take it. Fork it. Build your own version for your own network. The README has the full architecture, the agent prompt, and a sample post showing what passes the evidence test (and what fails). If three of you build your own Tailwind Tuesday this month, the experiment was worth it. → github.com/SimonTheSalesBooster/tailwind-tuesday PS .. yes, the post you might be reading from me one of these Tuesdays could be about you. The agent does not know yet who it picks next week. Neither do I.

Advisor Playbook open-sourced

Wed, 22 Apr 2026 06:20:41 +0000

Last quarter these 5 decision frameworks saved us from two bad trades, killed two underperforming cold-email campaigns, and moved one private client from $1.3M to $3M/year in 90 days. Open-sourced today. The Advisor Playbook: → Kill Triggers (when to sell) → Un-Buy Review (would I buy this today?) → Temperature Gauge (when standard rules stop applying) → Task-Loss reframe (neutralize the #1 B2B AI objection) → Fungibility Test (is AI going to sort you out?) Adapted from Howard Marks and Marc Andreessen. Running daily inside Strategy Sprints. MIT license. Steal them. https://github.com/SimonTheSalesBooster/advisor-playbook

Jetpack Sheet — what it is

Tue, 21 Apr 2026 12:05:31 +0000

Most founders watched an AI workshop last quarter. How many have an agent running today? Almost none. The gap is not the content. It's the install step. We just shipped the Jetpack Workshop Execution Sheet. Six rungs from "I watched the workshop" to "my first agent in production": 1. Pick the one trigger you want automated 2. Write the 5-question agent brief 3. Test it in a sandbox thread 4. Install it on your machine with screenshots and troubleshooting 5. Connect the one tool that matters 6. Run it for 72 hours, log what breaks, iterate Step 4 is where most guides die. We wrote it with the same screenshots we use inside the paid Jetpack cohort. This is the ladder most founders are missing. Link in comments.

Sales forces shrinking (evergreen)

Fri, 17 Apr 2026 08:12:00 +0000

Block cut 40% of its workforce. Stock jumped 18% the same day. The sales floor as we knew it is over. Recent shifts: .. Block: 10,000 to 6,000 employees. Profit guidance raised +54%. .. Salesforce: 9,000 to 5,000 support roles. Benioff on record: "I need less heads." .. Meta: $2.4M revenue per employee. Up 85% in 3 years. .. 36% of B2B companies cut their SDR team. Highest cut rate of any role. The pattern is identical everywhere. Headcount down 30 to 50%. Revenue per employee up 15 to 85%. Markets rewarding every announcement. The quiet version is scarier. Most companies aren't firing reps. They just stopped backfilling when reps leave. If you run a B2B business with 5 to 10 people, the question isn't "will this reach me?" It's "which of my 3 competitors rebuilds their GTM first?" Move first. Own the advantage. Grab a coffee if this is where you are: calendly.com/simonseverino/coffee-with-simon