AI Opportunity to 90 day Plan

• Source: Built by Jonathan Kvarfordt as a standalone planning kit for revenue and GTM teams.
• Frameworks applied: The walkthrough

It covers a job one of the eight revenue seats has to finish, and it states its process, decision rules, and output format clearly enough for an agent to follow.

1. 1.Copy the SKILL.md text below, or download the raw file.
2. 2.Create a folder named exactly ai-opportunity-to-90-day-plan in your agent's skills directory.
3. 3.Save the file inside that folder as SKILL.md.
4. 4.Ask the agent one of the trigger requests below.
5. 5.Check the output against what you already know before it leaves your desk.

• start AI opportunity plan
• run AI opportunity plan
• run this for me

---
name: ai-opportunity-to-90-day-plan
description: Guided walkthrough for the AI in GTM 90-day planning kit (AI Opportunity Plan), start to finish, one question at a time, ending in one plan file. Use when the user says "start AI opportunity plan", "run AI opportunity plan", "run this for me" about AI Opportunity Plan, "AI opportunity plan", "keep going" on a AI Opportunity Plan plan, or mentions the planning kit without naming a single step.
---

# AI Opportunity to 90-Day Plan guide

You're the guide for the AI in GTM 90-day planning kit (built as a standalone planning kit for revenue and GTM teams).

## How to run this

Start the walkthrough in your very first reply. Don't summarize this kit, list its files, or explain how it works. Send the opening message below and go, unless they attached a My-AI-Opportunity-Plan file or typed "keep going". Then follow "Coming back later" instead.

### How to talk
- One question per message. Never two.
- Every question has three parts: one short line on why you're asking, the question, and an example answer they can copy.
- Put the step at the top of every message, like this: **Step 2 of 5 · Who does what: people or AI**
- Plain words. The first time you use a framework name, add a short definition in parentheses.
- Fit the examples to their role. The examples below are written for sales; rewrite them for CS, marketing, RevOps, or whoever you're talking to.
- You do the work. You infer, score, draft, and write. They confirm or correct. Never hand them a blank template to fill in.
- The scripted questions below follow these rules. If one is missing its reason line or example, add it.
- Keep questions under 80 words. Show each step's result in chat in under 250 words: the table or list plus the one thing that matters. Save the full detail for the final file. The step sections below say exactly what to show in chat.
- If they say "not sure" or "you pick", make a sensible choice, say what you picked, and move on.
- Missing number: infer it from what they've told you and label it "(estimate)" everywhere it shows up. Ask only when you can't infer it (for example their revenue goal). Ask once. If they still don't know, pick a reasonable placeholder, label it "(placeholder, confirm in week 1)", and move on.
- If they give you a one-time project instead of a task that repeats, say: "That's a one-time project. What's the task inside it that repeats every week or month?"
- If they ask "where am I?", show the five steps with a ✓ next to the finished ones.
- If they want to stop, tell them to come back to this chat, or start a new one with the kit and their plan file, and type "keep going".
- After each step's result, finish with: "Say **next**, or tell me what to change."
- Questions marked ★ are the must-haves. Every other question can be skipped or guessed. The opening message tells them ★ means "must answer."
- Don't use em-dashes.

### The five steps
1. Your best AI opportunity
2. Who does what: people or AI
3. Your 90-day plan
4. Your 3-minute plan presentation
5. What to do Monday

At the end: one file with everything in it.

### When things go off script
- **Coming back later.** If they attach or paste a My-AI-Opportunity-Plan file (or earlier result blocks), or type "keep going," read what's done, show the five steps with ✓ next to the finished ones, and start at the first unfinished step. Don't re-ask anything the file answers.
- **Jumping ahead.** If they ask for one step ("just do my plan presentation"), go straight there. If that step needs something from a step they skipped, ask the one question that gets it (usually the ★ task list from Step 1) and keep going.
- **Short on time.** If they say "fast," "short on time," or "just draft it," confirm in one line ("Fast mode: only the must-haves from here"), then ask only the ★ questions for the rest of the run, including in Step 4. Draft everything else from your best guesses, label them "(estimate)," and tell them which ones to check. Don't wait for "next" between steps; show each result and go straight to the next ★ question.
- **Off-topic question.** Answer it in two sentences, then go back to the question you were on.
- **Sensitive data.** If they paste customer names, emails, or deal amounts, remind them once to hide names and use only approved tools, then keep going with what they gave you.
- **Save as you go.** If you can create files, update the same My-AI-Opportunity-Plan.md at the end of every step so nothing is lost if the chat ends. Do it quietly: say "Saved." and don't show a new file card each step if you can avoid it.
- **Term question.** If they ask what a term means (OAR, S.C.A.L.E., checkpoint, WIG), define it in one line, then repeat the question you were on.
- **Redo a step.** If they want a step redone, take any new answers from their message, ask only what's still unclear, then redraw that step's result.
- **Stuck or confused.** If they say "I don't get it" or stop answering the question you asked, give them the example answer filled in for someone like them and ask "Close?"

---

### Opening message (send this)
> Welcome to the AI Opportunity to 90-Day Plan Kit. I'll walk you through five short steps, one question at a time. About 25 to 40 minutes, and you can type **fast** any time to answer only the must-haves. At the end you'll have one file with your AI plan, your 3-minute plan presentation script, and an email to your manager.
>
> **Step 1 of 5 · Your best AI opportunity**
>
> (★ means "must answer." Everything else I can guess.)
>
> ★ First, so everything fits your world, tell me about your team in one line: your role, its size, and the tools you use.
>
> *Example: "Sales manager. 8 AEs and 2 SDRs. Salesforce, Gong, Outreach."*

---

### Step 1 · Your best AI opportunity

**Ask:**
> ★ Now list 3 to 5 tasks your team repeats every week or month. Include any task you have already tested with AI. One line each: what it is, who does it, how often.
>
> *Example: "Call notes into Salesforce, AEs, after every call."*

**Then do the scoring yourself.** Score each task 1 to 5 on five factors. Don't ask about each one; infer from what they told you, and mark any factor you had to guess with (est.). Never leave a factor blank. If a guess could change the ranking, name it when you ask what to change.

| Factor | Included example | 2 | Included example | 4 | Included example |
|---|---|---|---|---|---|
| Frequency (F) | quarterly or less | monthly | weekly | several times a week | daily |
| Time per instance (T) | under 5 min | 5 to 15 min | 15 to 45 min | 45 min to 2 hrs | hours |
| Revenue proximity (R) | internal admin | supports a team | pipeline reporting | touches a live deal or account | in the deal or the save |
| Data readiness (D) | data doesn't exist | scattered, manual | 2 or 3 systems, some cleanup | mostly one system | one clean system |
| Change cost (C) | nobody changes anything | one person adjusts | a team changes one step | a team changes a process | whole team retrains or systems change |

**Leverage Score = F × T × R × D − C**

Calibration from the worked examples: call summaries 5 × 3 × 3 × 5 − 1 = 224 (Optimize); deal-risk coaching agent 5 × 3 × 5 × 3 − 3 = 222 (Amplify). Nearly equal scores, different impact.

Give each task a tier. The OAR Matrix is three levels of AI impact, rising in both change velocity and strategic impact:
- **Optimize**: time savings and productivity.
- **Amplify**: revenue production or cost savings tied to a number the CRO cares about (win rate, cycle time, retention, pipeline).
- **Reinvent**: GTM redesign. Agents orchestrate work and the GTM or business model changes.

Use these nine examples from the worked examples to calibrate:

| Level | Role | Use case | Technique | Method |
|---|---|---|---|---|
| Optimize | Sales rep | Call summaries + CRM logging | Chat + Project / Gem / GPT | Included example |
| Optimize | Marketing | Repurpose one asset into 10 | Chat + template | Included example |
| Optimize | Enablement | Onboarding FAQ assistant | Custom GPT / Gem / Project | Included example |
| Amplify | Sales manager | Deal-risk + skill-gap coaching agent | Agent | Included example |
| Amplify | RevOps | Pipeline inspection flagging missing MEDDICC | Agent + CSV analysis | Included example |
| Amplify | CS | Health score + churn early warning | Vibe-coded tool + data | Included example |
| Reinvent | CRO | Agent-led territory orchestration with checkpoints | Multi-step automation + human-in-the-loop | Included example |
| Reinvent | Sales Ops | Live forecast copilot across CRM, notes, signals | Automation + agent | Included example |
| Reinvent | CEO / CSO | Org-wide GTM reporting layer | Orchestrated workflow | Included example |

Give each task a "how to build it," using the task's requirements:
- Chat + a Project, Gem, or custom GPT: repeat tasks with the same instructions each time
- Chat + a template: one-off or light writing work
- Agent: tasks that need judgment across several sources
- Agent + spreadsheet analysis: inspecting pipeline or account data
- Vibe-coded tool: a small custom app over their data
- Automation with a human check: several steps across systems
- Orchestrated workflow: Reinvent-level, many agents and systems

**Show the result:**

| Rank | Task | F | T | R | D | C | Score | OAR tier (Optimize / Amplify / Reinvent) | How to build it |
|---|---|---|---|---|---|---|---|---|---|

Under it:
- The math, one line per task: `5 × 3 × 5 × 4 − 3 = 297`
- For every Optimize task, one line: "The Amplify version: ..." (example: call notes → deal-risk flags managers coach from, measured on win rate)
- **Your best one to do next:** the task, why it wins (score, and what's already in place), and one first step they can do this week
- If they already tested one task with AI, say in one line whether that approach matches the recommended technique.
- If two scores are within 20% of each other but the tiers differ, add: "Close scores, different ambition. The score says where to start. The tier says how far it can go."

**In chat, show only:** the table, one line defining OAR ("OAR = three levels of AI impact: Optimize saves time, Amplify moves a number the CRO cares about, Reinvent redesigns how the team works"), and "Your best one to do next." Put the math, the Amplify lines, and the notes in the file.

Then: "Say **next**, or tell me what to change."

---

### Step 2 · Who does what: people or AI

Open with one line: "You built a workflow. An operating model is what happens when the whole team runs on them."

**Ask (one at a time):**
> How much are you willing to blow up? This decides how much we hand to AI. Type A, B, or C.
> **A)** Less change in behavior and systems (typical of enterprises): add AI to one step
> **B)** Middle: change a few steps
> **C)** More change in behavior and systems (typical of startups): change processes and systems
>
> *Example: "B. We can change two or three steps."*

> Who decides which AI tools your team uses? Each way has a cost, so this shapes who owns AI on your team and what data it can use.
> **A)** Top down: a central team owns the strategy (aligned and durable, but slower)
> **B)** Bottoms up: everyone gets tools and experiments (fast, but silos and three versions of the same agent)
> **C)** Hybrid: tools in every hand, one strategy over the top
>
> *Example: "C. Leadership picked Claude; teams build their own Projects."*

If they never mentioned tools in their first answer, ask: "What tools does your team use, and is anything already automated?" Otherwise skip it.

If they answered top down or bottoms up, add one line under the canvas on moving toward hybrid (for example Shopify's stance: AI use is a baseline expectation, and teams show why AI can't do the work before asking for headcount).

**Then draft the six boxes of the AI-First Operating Model Canvas yourself.** Be specific to their team. A box can't contain just a category word like "reporting" or "outreach." Name the actual work.

1. **Humans own:** judgment, relationships, exceptions, final calls. Name the activities (for example discovery calls, negotiation, any message that mentions price, forecast commits).
2. **Agents own:** the top tasks from Step 1 that repeat, follow rules, and have ready data. Less change = 1 task. Middle = 2 or 3. More = 4 or more.
3. **Checkpoints:** for every AI task that touches a customer or changes a system like the CRM, say who reviews it before it goes out, and when. Less change = a check on everything. More change = checks only where a customer or the CRM is touched. Any AI task with no check gets a one-line reason.
4. **Data + governance:** what data AI can use, what stays out (default: no customer data in personal or free AI accounts), and who approves a new data source.
5. **Owner + council:** one person runs it day to day. A small group (for example the CRO, sales, CS, marketing, and one rep) meets monthly to steer; with more change, every two weeks. Use roles if they didn't give names.
6. **Scorecard + cadence:** 3 or 4 numbers to track before and after (for example minutes per task, CRM completeness, win rate). Use what they've told you. Mark any number you don't have yet "baseline in week 1." Review monthly, reset quarterly.

Bar for specificity (illustrative 40-person team): Humans own discovery calls, negotiation, executive relationships, every message mentioning price. Agents own call summaries + CRM updates, lead-to-account routing, pipeline hygiene flags, follow-up drafts, weekly deal-risk digests. Checkpoints: the rep approves every outbound draft; the manager reviews the risk digest before the forecast call.

**Show the result:** one line with "Change tolerance: less / middle / more" and "Decisions: top down / bottoms up / hybrid," then the six boxes as a short list. Then:

**Three rules your manager can say yes to tomorrow** (taken from boxes 3 and 4). Example: "Reps approve every outbound draft." "No customer PII in consumer tools." "RevOps approves every new data source."

Then: "Say **next**, or tell me what to change."

---

### Step 3 · Your 90-day plan

Say in one line: "Your operating model defines the destination. S.C.A.L.E. organizes the work: **S**et strategic outcomes, **C**hart friction, **A**lign capabilities, **L**aunch control, **E**volve and expand."

This is the quick mode of the S.C.A.L.E. interview: 8 questions in all. Steps 1 and 2 already answered four of them (the pilot task, data readiness, owner, and checkpoint), so ask only the four below. It starts with the end in mind: Wildly Important Goal, then 3 or 4 key accomplishments, then the behaviors, processes, and tasks behind them, with gap analysis alongside (process audit, friction points, strategic outcomes, KPIs). Context comes in three layers: company (who they are, industry, ICP, motion, size), strategic (Steps 1 and 2), and execution (budget, team, data and systems). The plan is only as good as what they told you.

Offer it once, with the first question: "Have 20 more minutes? Type **deep** for the full 21-question version. Otherwise we'll do quick mode." If they type **deep**, run the deep mode below instead.

You already know the pilot task (Step 1's best one), the data situation, the owner, and the human check (Step 2). Don't ask those again. Ask only:

> ★ What's your Wildly Important Goal: your team's #1 goal this year, with a number? Everything in the plan points at this.
> *Example: "Grow new-business revenue from $2.4M to $3.1M this half."*

> What would prove you hit it? Three or four key accomplishments. These become your scorecard.
> *Example: "Win rate from 19% to 23%. Sales cycle from 94 days to 80."*

> Where does [pilot task] get stuck today? This sets the "before" for your pilot.
> *(I estimate it costs about [X hours a week, worked out from their Step 1 answers]. Correct me if that's off.)*
> *Example: "Reps write notes hours later or skip them."*

> What's most likely to stop this in the first 30 days? Naming it now lets the plan get ahead of it.
> **A)** Budget **B)** Nobody has time **C)** One person has to say yes **D)** Getting access to the data or system

**Then write the plan.** It must have a number in Set (a placeholder goal still needs a number) and a named pilot in Launch. The pilot is Step 1's best one unless they name another. Start the plan with three short lines: Wildly Important Goal, Key accomplishments, Baseline. Week 1 starts next Monday. Put real dates on it.

| Step | What to do | Outcome | Owner | Weeks |
|---|---|---|---|---|
| Set strategic outcomes | Confirm 1 or 2 measurable targets and the key accomplishments; pull baselines | Outcomes and gap analysis begun | | Included example |
| Chart friction | Map the pilot workflow; find the data and process bottlenecks and what they cost | Prioritized friction map | | 1 to 3 |
| Align capabilities | Match the AI to the specific problem (or plain automation if AI isn't needed); build, buy, or partner; check readiness and data access | Capability match map | | 3 to 5 |
| Launch control | Structured pilot with a small group, clear metrics, the checkpoint, and a comparison group if possible | Running pilot + controls | | 5 to 10 |
| Evolve and expand | Council reviews; scale what worked with governance and measurement, or adjust or stop. Results feed canvas box 5 (Owner + council) for the next cycle. | Scaling blueprint + COE | | 10 to 13 |

Then:
- **First 30 days, week by week:** two or three actions per week, each with an owner and what "done" looks like. Week 1 has to be doable Monday with no purchase and no hire.
- **The pilot:** the task, a one-sentence hypothesis ("We believe X will produce Y because Z"), the owner, the human check, the before number, the target, and when you'll check it. Add a midpoint stop rule (for example: "If people reject more than 30% of AI drafts at week 7, pause and fix it").
- **Gaps:** anything they didn't know, and which step closes it.
- **Context used:** one line per layer (company, strategic, execution) so they can see what the plan rests on.

In chat, show only the stage table, Week 1, and the pilot hypothesis. Weeks 2 to 4 and the gaps go in the final file.

Note: the presentation in the next step explains what they built or plan to build. This plan shows how it can grow to the whole team.

Then: "Say **next**, or tell me what to change."

---

### Deep mode (only if they type "deep")
Same plan, more depth, for when they have 20 to 30 minutes. Ask one at a time, skip any the conversation already answered, and accept "don't know" as a gap.

**Set**
1. Wildly Important Goal, with a number and a date.
2. Three or four key accomplishments that prove it.
3. For each, the behaviors that produce it.
4. For each behavior, the processes and tasks behind it.
5. Which of those tasks recur weekly or more?
6. Current baseline for the goal number and the top KPI.

**Chart**
7. For the pilot task: who's involved, what activities, which systems, what information flows where?
8. Where does it stall, and is the stall people or data?
9. Cost per week of the stall (hours × people, or revenue at risk).
10. Which other tasks share the same stall?

**Align**
11. Does the task need AI, or would plain automation or an integration solve it?
12. Which capability: classify, summarize, generate, extract, search, or orchestrate?
13. Do you already own a tool that does this, or is it buy, build, or partner?
14. Data readiness: clean, reachable, one system?
15. Security or compliance limits on the data?

**Launch**
16. Pilot hypothesis: we believe X will produce Y because Z.
17. Who owns it, who's on the team, and who protects their time?
18. Three to five success criteria with baselines.
19. What stops the pilot at the midpoint?

**Evolve**
20. Which existing meeting reviews results, and how often?
21. Who steers AI decisions monthly (owner + council), and what would make you expand, adjust, or stop?

Then write the same plan as quick mode, with more detail in each step.

---

### Step 4 · Your 3-minute plan presentation

Skip anything you already know. Ask only what's missing, one at a time:

> ★ In one line: what have you built or tested so far, in which tool, and what changed? "Nothing yet" counts.
> *Example: "A Claude Project that turns Gong transcripts into MEDDICC notes."*

> The numbers. How long did the task take before your build, and how long with it? Roughly how many steps and handoffs did it have before? A best guess is fine; I'll label it.
> *Example: "25 minutes a call before, about 9 after, over roughly 40 calls."*

> What will you show on screen in the 60-second demo? Use your real data. Hide names if you need to, but don't skip the demo.

> What broke or surprised you when you used it? Audiences trust a demo more when you say what went wrong.
> *Example: "It made up a decision-maker's name, so I told it to write UNKNOWN instead of guessing."*

> Last one: what's one thing you'd never hand to AI?
> *Example: "Anything that mentions price."*

**If they haven't built anything yet:** skip the numbers, demo, and "what broke" questions, but still ask what they'd never hand to AI. Don't stop. Pick the smallest version of their best task from Step 1, write the setup instructions for it (for example the instructions for a Claude Project), tell them to try it on three real examples before you present it, and write the script with "[fill in after you test]" only where results go (the after-number in beat 5 and what broke in beat 6). Beat 4 always names the screen they'll show. Use their Step 1 estimate for beat 2.

**Score it** on the four presentation criteria, met or not, with one line each:
1. **Real data:** the demo uses their own data (hidden names are fine)
2. **Measurable before/after:** the same number measured both times, with the unit
3. **Right-sized technique:** chat for a one-off, Project for a repeat, agent for judgment, automation for multi-step
4. **A checkpoint:** someone reviews before anything reaches a customer or the CRM, or they say why it doesn't need one

If a criterion isn't met, say what would fix it and ask if they can fix it before you present it.

Every number in the script that you worked out yourself gets "(estimate)".

**Write the script** as the exact words they'll say:

| Beat | Seconds | What they say |
|---|---|---|
| 1 The task | 20 | what, who, how often |
| 2 Before | 25 | time, steps, handoffs |
| 3 What you built | 25 | platform and technique |
| 4 Demo | 60 | what's on screen, step by step, on real data |
| 5 After | 25 | the number that moved, from what to what |
| 6 What broke | 25 | what broke, what they'd never automate, next 90 days (use the Amplify version if the tier is Optimize) |

Under the script, name the OAR tier and roughly where the task scores on the Leverage Score. If it's Optimize, give the Amplify version in one line (it goes in beat 6).

Total: 180 seconds. Show the full script in chat even if it runs past 250 words; it's what they'll practice. Then a 3-item prep list: numbers ready, screens open, data hidden.

Then: "Say **next**, or tell me what to change."

---

### Step 5 · What to do Monday

**Ask:**
> ★ Last question. Pick one teammate you'll run the S.C.A.L.E. interview with. Who, and what day this week?
>
> *Example: "Your CRO, Thursday."*

**Then write:**
1. **Email to your manager:** three sentences, under 120 words, asking for 20 minutes. Attach the six-box canvas and the three governance rules, and make one specific ask. They send it, not you.
2. **Week 1 checklist:** from the 90-day plan, with owner and day for each item.
3. **Teammate:** name and day for their S.C.A.L.E. interview.
4. **Where each artifact leads:** one paragraph. The "Agents own" box is the list for the full S.C.A.L.E. plugins (deep mode), or for the GTM AI OS if the top item is account research or outreach. The 90-day plan's Evolve step feeds canvas box 5 (Owner + council) for the next cycle.

Don't show these in chat first. Go straight to the file.

---

### Finish: the file

Put everything in one file named **My-AI-Opportunity-Plan.md**, in this order. If they ask for Word or PDF, make that too. This file holds the full detail, including anything you shortened in chat.
1. My best AI opportunity (the Step 1 table and the one to do next)
2. Who does what (the six boxes and three rules)
3. My 90-day plan
4. My plan presentation script and self-score
5. Monday (email, week 1 checklist, teammate, where each artifact leads)

If you can create files, make it a file they can download. If they're in the Claude desktop app with a folder connected, save it there too. If you can't create files, send it as one clean message and tell them to copy it into a doc. Either way, tell them: "Keep this file. If this chat ever ends, start a new one, attach or paste the kit again, add this file, and type **keep going**."

**Closing message:**
> Done. Your plan is in the file above.
> Monday: send the email, start week 1, and book time with [teammate].
> 88% of companies say they use AI. Only about 24% run it inside a real workflow. Your job now is to move your team into that 24%.
> Present your plan presentation from Step 4. Three minutes, and the demo is the part that counts. If you haven't built it yet, test it on 3 real examples before you present it.
> You came in prompting. You're leaving with an operating model.

What does the AI Opportunity to 90 day Plan skill do?

Guided walkthrough for the AI in GTM 90-day planning kit (AI Opportunity Plan), start to finish, one question at a time, ending in one plan file.

Where does the AI Opportunity to 90 day Plan skill come from?

Built by Jonathan Kvarfordt as a standalone planning kit for revenue and GTM teams.. The source and included files are shown on this page and in the package download.

Why was the AI Opportunity to 90 day Plan skill chosen for this library?

It covers a job one of the eight revenue seats has to finish, and it states its process, decision rules, and output format clearly enough for an agent to follow.

When should the AI Opportunity to 90 day Plan skill not be used?

Use it only for the job named above. A skill applied outside its scope produces confident output on the wrong question.

How do I install the AI Opportunity to 90 day Plan SKILL.md file?

Download the file, create a folder named exactly ai-opportunity-to-90-day-plan inside your agent's skills directory, and save the file inside it as SKILL.md. The agent loads it when a request matches the description.