ChatGPT prompts for B2B sales that don't sound like a robot.
Organized by funnel stage. Tested on real pipelines. Zero fluff. Copy, paste, adjust the bracketed bits, send.
100 prompts10 categoriesFree foreverWorks with Claude & Gemini too
Most "ChatGPT for sales" prompt lists are written by people who've never sent a cold email. You can tell because the outputs read like a press release wrote them. The prompts below force specificity: a named trigger event, a concrete pain, a single clear ask. That's the difference between 4% reply rates and 0.2%.
Every prompt here is a copy-paste template. The bracketed placeholders, [like this], are where you plug in your own detail. Don't skip them. Lazy inputs produce lazy outputs, and everyone with an inbox has learned to smell generic AI-generated pitches from three scrolls away.
01
Prospecting & Research
Turn a company URL, a LinkedIn profile, or a news alert into a qualified opportunity with context you can actually use.
Account research brief in 90 seconds
PROMPT 001 / 100
Before any outbound touch, get a one-page read on the account.
You are a B2B sales analyst. Given the company below, produce a one-page research brief in under 300 words. Company: [COMPANY NAME] Website: [URL] My product: [ONE LINE DESCRIPTION] Return exactly these sections: 1. What they do (one sentence, no marketing language) 2. Signals of growth or pain (recent hires, funding, layoffs, product launches) — cite sources 3. Who likely owns the buying decision for my product (title + reporting line) 4. One specific hook I can use in a cold email, tied to something I found in section 2 No fluff. No "in today's competitive landscape." Get to the point.
The 'no fluff' line is load-bearing. Without it, GPT adds a paragraph of LinkedIn poetry at the top.
Decision-maker finder from a company
PROMPT 002 / 100
Identify the right person to contact when only the company is known.
Company: [COMPANY NAME] My offer: [ONE LINE] Deal size: [$X] Based on this, tell me: 1. Exact job titles most likely to own this decision (list 3, in order of likelihood) 2. Who influences the decision but doesn't own it (list 2) 3. Which title to email FIRST and why (gatekeeper risk, reply rate, ability to champion) 4. Red-flag titles that will kill the deal if looped in too early Assume a company of [HEADCOUNT] employees and [INDUSTRY].
The red-flag titles output is gold. It surfaces the procurement-shaped landmine before you step on it.
Trigger event scanner
PROMPT 003 / 100
Find a reason-to-reach-out that isn't 'I saw your website.'
For the company [COMPANY], scan for the following types of trigger events in the last 90 days: - Funding rounds or M&A activity - Leadership hires at VP+ level (especially in [RELEVANT DEPARTMENT]) - Product launches or major feature releases - Expansion into new markets or geographies - Public statements or earnings comments about [RELEVANT PAIN] - Layoffs, restructuring, or org changes - Industry awards, keynote talks, major press For each trigger you find, give me: the event, the date, the source URL, and one specific angle I could use to open a conversation. If you can't find anything genuine, tell me that plainly. Do not fabricate.
The 'do not fabricate' line is non-negotiable. LLMs will invent plausible-sounding funding rounds if you let them.
LinkedIn profile → qualification read
PROMPT 004 / 100
Pasted LinkedIn bio → instant buyer snapshot.
Paste below is someone's LinkedIn profile (headline, about, experience, recent posts if available): [PASTE PROFILE TEXT] I sell [PRODUCT] to [ICP]. In under 200 words, tell me: 1. Are they in my ICP? (yes/no/borderline — and why) 2. What are they publicly trying to do right now in their role? 3. What's one thing in their profile I could reference that would NOT feel like a stalker move? 4. Priority: HIGH / MEDIUM / LOW / SKIP — and the reason
The 'NOT feel like a stalker move' constraint produces wildly better openers than 'personalize this.'
Website scan for buying intent
PROMPT 005 / 100
Pull pain signals straight from a prospect's own marketing site.
I'm going to paste the homepage and pricing page content from a prospect's website. Analyze it and tell me: 1. What are they positioning against (who's the implicit competitor)? 2. What pains are they promising to solve for their customers? (list 3) 3. Any clues about their tech stack or current vendors? 4. Anything that suggests they're missing [MY PRODUCT'S CAPABILITY]? 5. If you were me selling [PRODUCT], what would your opening line be? Content: [PASTE HERE]
Works even better when you paste their About page. Founders' stories leak a lot of commercial pain.
Industry-wide opportunity scan
PROMPT 006 / 100
Identify the best-fit vertical segments inside a broader industry.
I sell [PRODUCT/SERVICE]. My current best customers are [3-4 EXAMPLES]. I want to expand into [BROADER INDUSTRY]. Break that industry into 8-12 sub-segments and rank them by: - Fit with my product (based on the pattern across my current customers) - Likely budget availability in 2026 - Accessibility (are there clear lists? Events? Trade orgs?) - Competitive density (am I fighting 20 vendors or 2?) For the top 3 sub-segments, give me: 5 example target companies, 2 trade publications, and 2 industry events worth attending.
Feed this to Claude Opus. It's noticeably better than GPT at the segmentation logic.
Account prioritization from a list
PROMPT 007 / 100
Rank a long list of accounts when time is the constraint.
I have [NUMBER] target accounts in my territory. My product is [PRODUCT], and my best-fit customer looks like [ICP CRITERIA]. Here's the list with one line each on revenue / headcount / industry: [PASTE LIST] Sort them into three tiers: - TIER 1: Immediate outreach (strong fit + buying signals) - TIER 2: Outreach in 30 days (good fit, lower urgency) - TIER 3: Nurture only (weak fit, no signals) For each TIER 1 account, give me a one-line reason to prioritize and a suggested opening angle.
The three-tier structure prevents GPT from flattening everything into 'these all look promising.'
Persona-specific pain mapper
PROMPT 008 / 100
What keeps this persona up at night, specifically.
Persona: [JOB TITLE] at a [COMPANY TYPE] with [HEADCOUNT] employees. Map the top 5 pains this persona actually has day-to-day. For each pain, give me: - The pain stated how they would describe it (not how a marketer would) - Who currently gets blamed for the pain inside the org - What they've likely already tried that didn't work - The metric they're measured on that this pain affects - The emotional weight (annoyance / stress / career-threatening) Avoid generic "efficiency" and "productivity" language. Be specific enough that a real [PERSONA] would nod.
The 'not how a marketer would' constraint is the whole game. Without it, you get buzzword soup.
Intent signal interpreter
PROMPT 009 / 100
Translate raw signal data (G2 page views, job postings, etc.) into an outreach angle.
Here's the signal data I have on [COMPANY]: [PASTE SIGNALS — e.g., "Viewed our pricing page 3x in last 7 days", "Posted job for Head of Revenue Ops", "Recent podcast appearance discussing attribution"] Translate this into: 1. What are they probably working on right now? 2. What's the most likely internal trigger? 3. What's the RIGHT moment to reach out — today, next week, next month? 4. What's the angle that ties the signals together in one coherent opener?
Great for 6sense / Bombora exports. Turns signal noise into a sentence.
Competitor displacement research
PROMPT 010 / 100
Find accounts actively frustrated with a specific competitor.
I sell [PRODUCT]. My main competitor is [COMPETITOR]. I want to find accounts where people are publicly complaining or showing switching signals. Give me a research plan: 1. Which public channels are most likely to surface complaints about [COMPETITOR]? (G2, Reddit, X, review sites, forums — be specific to their category) 2. What search strings should I use on each? 3. What job titles should I monitor on LinkedIn for "recently left [COMPETITOR-USING-COMPANY]" signals? 4. What's the ethical cold-email approach to someone clearly unhappy with [COMPETITOR]?
The ethical framing matters. Competitor displacement done wrong is a fast path to being blocked everywhere.
02
Cold Email (Opener)
The first email is 80% of the outcome. These prompts force specificity, brevity, and a single clear ask.
The three-sentence cold opener
PROMPT 011 / 100
The default cold email template that actually gets replies.
Write a cold email under 75 words total. Three sentences maximum. Structure: Sentence 1: A specific observation about [PROSPECT] or [COMPANY] — something I could only know by paying attention. No flattery. Sentence 2: The pain that observation implies, in the prospect's own language. Sentence 3: One concrete, low-commitment ask — not a meeting, not a call. A reply or a one-click yes/no. Context: - Prospect: [NAME, TITLE, COMPANY] - My product: [PRODUCT] - The observation I want to anchor on: [OBSERVATION] Hard rules: no "hope this finds you well", no "quick question", no "I know you're busy", no em dashes, no three-part lists.
The 'no em dashes, no three-part lists' line kills 90% of the AI tells in one shot.
The trigger-event opener
PROMPT 012 / 100
When you have a specific, recent event to anchor on.
Write a cold email under 80 words that opens with a recent trigger event. Trigger event: [EVENT — e.g., "your Series B announcement last week"] My product: [PRODUCT] The implied pain this creates for [PROSPECT TITLE]: [PAIN] The ask: [SPECIFIC, LOW-EFFORT ASK] Structure: - Line 1: Reference the trigger event in a way that shows I read beyond the headline - Line 2: Connect it to a specific operational challenge [PROSPECT TITLE] will now face - Line 3: Offer something concrete that maps to that challenge - Line 4 (optional): Ask a one-word reply question Tone: conversational, peer-to-peer. Not "congratulations on your success."
'Read beyond the headline' is the magic instruction. Forces the model to find a second-layer detail.
The counterintuitive-claim opener
PROMPT 013 / 100
Pattern-interrupts when the whole inbox is already saying the same thing.
Write a cold email where the first line is a counterintuitive claim about [PROSPECT]'s industry — something they'd agree with in private but wouldn't post on LinkedIn. My product: [PRODUCT] Prospect: [TITLE] at [COMPANY] The underlying truth I want to reference: [TRUTH — e.g., "most CRM hygiene projects fail because the real problem isn't data, it's that reps have no incentive to update fields"] Structure: - Opener: the uncomfortable truth, stated plainly - Middle: one sentence on why this matters for their role specifically - Close: an ask that's genuinely interesting, not "jump on a call" Under 90 words. No jargon. Don't overexplain.
The best opener I've seen for senior buyers. They're tired of being flattered. A truth they recognize cuts through.
The tiny-ask opener (no meeting)
PROMPT 014 / 100
When the prospect's calendar is already a war zone.
Write a cold email that does NOT ask for a meeting, a call, or 15 minutes of time. Instead, ask for a one-click response — like "yes / no / not now" — or a reaction to a specific idea. Context: - Prospect: [TITLE] at [COMPANY] - My product: [PRODUCT] - The specific micro-question I want an answer to: [QUESTION] The email should be under 60 words. The ask should feel like it takes 3 seconds to answer, not 30 minutes to schedule. Assume they'll read this on their phone between meetings.
Conversion on this is 3-5x higher than 'grab 15 mins' asks. You just have to be OK with smaller conversations first.
The contrarian case-study opener
PROMPT 015 / 100
When you have a customer win that contradicts what the prospect probably believes.
Write a cold email built around a counterintuitive customer outcome. The customer story: [CUSTOMER + SPECIFIC OUTCOME, e.g., "[COMPANY X] cut their SDR team in half and DOUBLED booked meetings in 60 days"] Why this contradicts common belief: [REASON] Prospect: [TITLE] at [COMPANY] Why this should matter to THEM specifically: [WHY] Structure: Lead with the surprising outcome. Spend one sentence on why it's surprising. One sentence on the mechanism. One sentence asking if the same thing would apply to them. Under 100 words. Read like one human telling another human about something interesting, not like a case study sales pitch.
'Like one human telling another' is the reframe. Drops the press-release register immediately.
The mutual-connection opener (done right)
PROMPT 016 / 100
Using a shared connection without sounding sleazy.
I have a mutual connection with [PROSPECT]: [MUTUAL CONNECTION NAME]. They have NOT offered to intro me — I'm cold. But I want to reference the connection honestly without making it sound like a warm intro. Write a cold email that: 1. Mentions [MUTUAL] only if it's genuinely relevant (don't force it) 2. References something specific about what [MUTUAL] and I have discussed or worked on 3. Makes clear I'm NOT pretending this is an intro 4. Has a reason-to-respond that stands on its own, not on the mutual Context: - Prospect: [TITLE] at [COMPANY] - Mutual: [NAME, THEIR ROLE/RELATIONSHIP TO ME] - My product: [PRODUCT] Under 100 words.
The honesty about not being a warm intro is the thing. Everyone's seen fake warm intros. Being straight about it is disarming.
The problem-video opener
PROMPT 017 / 100
For high-ticket sales where a 90-second personalized video beats an email.
I'm going to record a 60-90 second personalized video for [PROSPECT]. Write me the script. Context: - Prospect: [NAME, TITLE, COMPANY] - Specific thing I noticed about their operation: [OBSERVATION] - My product: [PRODUCT] - The outcome I want from this video: [E.G., reply with interest, accept a meeting] Structure: - First 5 seconds: use their name and one hyper-specific detail that proves I'm not spamming - Seconds 5-30: the problem I think they have, described the way they'd describe it - Seconds 30-50: one line about what I do and one specific result from a similar company - Final 10 seconds: a clear, low-pressure ask Write it to be SPOKEN, not read. Short sentences. Natural pauses. No "I hope you're doing well."
The 'written to be spoken' line is essential. Otherwise you get a paragraph that sounds like a TED talk.
The open-loop opener
PROMPT 018 / 100
Triggers curiosity without being clickbaity.
Write a cold email that opens a loop — raises a question in the prospect's mind — without being gimmicky. Context: - Prospect: [TITLE] at [COMPANY] - My product: [PRODUCT] - The genuine insight or pattern I've noticed (that they'd be curious about): [INSIGHT] The email should: 1. State the insight as an observation, not a tease 2. Hint at the mechanism without spelling it all out 3. Invite them to ask "how?" or "why?" — but let them decide whether to bite 4. Not pretend I know their business better than they do Under 80 words. No "I have a secret that will transform your business." That's a closed loop. I want an open one.
The distinction between open loop and clickbait matters. Open = genuine incomplete thought. Clickbait = withheld information.
The PS-carries-the-weight opener
PROMPT 019 / 100
Double-entry point: main body + PS doing different jobs.
Write a cold email where the main body is one job and the PS is a completely different job. Prospect: [TITLE] at [COMPANY] My product: [PRODUCT] Main body (3-4 sentences): a tight, specific value prop tied to [SPECIFIC TRIGGER OR OBSERVATION]. PS line (1 sentence): something personal, warm, or funny that shows I'm a human. Could be: a specific thing I liked about their recent post, a question about their company's coffee order, a joke about their city. The PS should NOT repeat or summarize the main ask. It's a second entry point for a reply.
The PS often gets more replies than the body itself. People are reading on phones and scanning for the human signal.
The reverse-pitch opener
PROMPT 020 / 100
Lead with what you DON'T do — disarms the pitch-fatigued reader.
Write a cold email that opens by explicitly saying what I DON'T do or what I'm NOT pitching. Context: - Prospect: [TITLE] at [COMPANY] - My product: [PRODUCT] - What they probably ASSUME I'm pitching (the common category they'd lump me into): [ASSUMPTION] Structure: - Opening line: "I'm not going to pitch you [ASSUMPTION]." - Second line: what I actually want to talk about - Third line: why that's different from what lands in their inbox every day - Closing ask: a specific, light question Under 80 words. This is a pattern interrupt — the tone should feel like relief, not sales.
Works disproportionately well with senior buyers who've learned to delete the first line on instinct.
03
Cold Email (Follow-up)
80% of replies come from follow-ups, not first touches. Most follow-ups are just 'bumping this' — which is why they don't work. These don't do that.
The value-add follow-up (no ask)
PROMPT 021 / 100
Send something actually useful instead of 'just circling back.'
Write a follow-up email to [PROSPECT] who didn't reply to my first message. I want this one to contain zero ask — no meeting request, no question requiring a reply. Context: - Original email was about: [TOPIC] - Their likely reason for not replying: [REASON] - Something I can share that's genuinely useful for them, with no strings: [ASSET — e.g., a specific teardown, a tool, a data point, a 2-minute video] Structure: - Line 1: don't apologize, don't say "following up" - Line 2: give them the useful thing - Line 3: one sentence on why I thought of them specifically for it - No PS, no CTA Under 50 words.
No-ask follow-ups break the sales cadence pattern. That's the point. Reply rate triples.
The new-information follow-up
PROMPT 022 / 100
Follow-up earns its place by bringing something the first email didn't.
Write a second-touch follow-up that is NOT a restatement of the first email. The follow-up must introduce new information that wasn't in email #1. Original email sent: [DATE] Original ask: [ASK] New information I now have (pick the strongest): [NEW INFO — recent event, new data point, new case study, industry news that strengthens my point] Structure: - Line 1: the new information (no "checking back in") - Line 2: how it changes or sharpens what I said before - Line 3: the original ask, reframed in light of the new info Under 75 words. If I can't think of new information, tell me the follow-up shouldn't be sent and suggest waiting.
The 'tell me the follow-up shouldn't be sent' line is what makes this prompt actually useful. Most follow-ups shouldn't exist.
The polite breakup email
PROMPT 023 / 100
The final email in a cadence. Gets more replies than all the middle ones combined.
Write a final "breakup" email for a prospect who hasn't replied to 4+ previous touches. Prospect: [TITLE] at [COMPANY] Original topic: [TOPIC] Structure: - Acknowledge that I've reached out several times - State clearly that this will be my last email - Give them an easy out ("if the timing's not right, just say so and I'll close the loop") - Offer one last small, useful thing (not a pitch) - Sign off warmly Tone: not guilt-trippy, not passive aggressive, genuinely fine with a no. Under 70 words. Hard rules: don't say "circling back", don't say "bumping this", don't use any variation of "I'm sure you're busy."
Breakup emails convert at 12-18% vs 2% for mid-cadence follow-ups. The exit is more interesting than the pitch.
The reference-their-reply follow-up
PROMPT 024 / 100
When they DID reply but said 'not now' or 'send me info.'
The prospect replied with: [PASTE THEIR REPLY] Write a follow-up that: 1. Takes their reply at face value — no trying to convert it into a meeting 2. Gives them exactly what they asked for, in a format they can consume in 90 seconds 3. Asks one specific follow-up question that moves the conversation forward WITHOUT pushing for a meeting 4. Leaves the ball in their court Under 80 words. Tone: helpful peer, not salesperson executing a playbook.
'Takes their reply at face value' is the whole thing. Most reps try to convert 'not now' into 'yes in 15 minutes on Zoom.' Don't.
The forward-to-the-right-person follow-up
PROMPT 025 / 100
When your first email was ignored but the person still might be the right entry point to route you.
Write a short follow-up that asks the prospect, politely, to forward me to the right person instead of engaging themselves. Context: - Prospect: [TITLE] at [COMPANY] - Why they might not be the right buyer but might know who is: [REASONING] - My product: [PRODUCT] Structure: - Line 1: no apologies, no "following up" - Line 2: one sentence acknowledging they might not be the right person - Line 3: ask specifically who on their team handles [TOPIC] — make this the easy reply - Line 4: optional one-line value prop they can forward if they choose Under 60 words.
The 'I think you might not be the right person' acknowledgment gives them a respectful exit. High forward rate.
The question-only follow-up
PROMPT 026 / 100
Zero pitch. One specific question. Often the best converter in a sequence.
Write a follow-up that contains ONE question and nothing else. No pitch. No recap. No signature flourish. Just a clean, specific, answerable question. Context: - Prospect: [TITLE] at [COMPANY] - What I most want to understand about their situation: [QUESTION TOPIC] The question should: - Be answerable in one sentence or less - Be specific enough that it's clearly for them, not a template - Not imply a pitch is coming if they answer Under 30 words total. One line. That's it.
Variant on the breakup, softer exit. Triggers loss aversion.
Write a short email asking the prospect for permission to mark them as "not interested" and stop following up. Context: - Prospect: [TITLE] at [COMPANY] - Number of prior touches: [N] - Original topic: [TOPIC] The email should: - State that I'd rather not keep bothering them if this isn't a fit - Ask explicitly for a thumbs-up on closing the loop - Make it clear that a "no" is totally fine and I'll stop reaching out - Keep the door open if timing changes Under 60 words. Warm. Zero passive aggression.
The loss aversion is real. 'OK to close the file' gets more 'actually wait let's talk' replies than any other follow-up.
The industry-news follow-up
PROMPT 028 / 100
Piggyback on something happening in their world, not yours.
Follow up with [PROSPECT] by referencing a specific recent piece of industry news. Context: - Prospect: [TITLE] at [COMPANY / INDUSTRY] - Original ask: [ASK] - Industry news to reference: [NEWS — must be from the last 14 days] Structure: - Line 1: the news, stated neutrally (no "you've probably seen") - Line 2: what it implies for their role or company specifically - Line 3: how it connects to my original ask - Line 4: the reframed ask, light and specific Under 85 words. Don't sound like I'm trying too hard to make the connection.
Industry news follow-ups feel less salesy than product-focused ones. Caveat: the connection has to be real, not forced.
The changed-my-mind follow-up
PROMPT 029 / 100
For when you genuinely reconsider something after reflection.
Write a follow-up where I admit I've rethought something from my original email. Original claim/point: [ORIGINAL POINT] What I've reconsidered and why: [UPDATED THINKING] How this changes what I'd actually suggest for them: [NEW ANGLE] Structure: - Line 1: admit the rethink simply, no performative humility - Line 2: state the updated take - Line 3: tie it to their situation with a new angle - Line 4: a new, better ask Under 90 words. Tone: thoughtful, not theatrical.
Demonstrated intellectual honesty is rare in cold outreach. It's memorable for that reason alone.
The soft-reference follow-up
PROMPT 030 / 100
Cite a similar customer without dropping a logo bomb.
Write a follow-up that references a similar customer without naming them explicitly (NDA or politeness reasons). Context: - Prospect: [TITLE] at [COMPANY] - Similar customer: describe them as "a [SIZE] [INDUSTRY] company with [RELEVANT TRAIT]" without naming - Specific, quantified result: [RESULT] - My original ask: [ASK] Structure: - Open with the nameless case study in one line - One line on why it's relevant to them specifically - Offer to share more detail (including the name, privately) if they want - Restate the ask Under 80 words.
The 'name privately if they want' line is clever. It creates a small opt-in that often becomes the reply.
04
LinkedIn Outreach
LinkedIn isn't email. The rules are different: shorter, more conversational, and the connection request is the real first touch — not the followup DM.
Connection request under 200 characters
PROMPT 031 / 100
The 200-char LinkedIn limit forces real discipline.
Write a LinkedIn connection request under 200 characters. Prospect: [NAME, TITLE, COMPANY] Specific hook (must reference something real from their profile or recent activity): [HOOK] Rules: - Must fit in 200 characters including spaces - Must NOT mention my product or company - Must NOT say "I'd love to connect" - Must give them an actual reason to accept beyond "another random request" - Can end with or without a question Give me 3 variations with different tones: curious, complimentary-but-specific, and useful (offering to share something).
3 variations with different tones is the key. You're building a toolkit, not picking one template.
First DM after connection accepted
PROMPT 032 / 100
The trickiest message. Too early = pitchy. Too late = forgotten.
Write the first DM to send after [PROSPECT] accepts my connection request. Context: - Days since they accepted: [N] - What I noticed on their profile that I'd legitimately want to know more about: [CURIOSITY HOOK] - My product: [PRODUCT] Rules for this message: - Do NOT pitch. Do not mention my product. Do not ask for a meeting. - Open with genuine curiosity about something specific to them or their work - End with ONE question that's easy to answer in one sentence - Under 60 words Think of it as starting a conversation with a peer at a conference, not opening a sales call.
The conference-peer framing is the reframe that makes this work. Everything else flows from that vibe.
The comment-on-their-post opener
PROMPT 033 / 100
Reach out via a thoughtful comment first, then DM.
Write a LinkedIn comment for [PROSPECT]'s recent post below. The comment should: 1. Add genuine value (a perspective, a counterpoint, a related example) — not just "great post!" 2. Reference something specific from the post 3. Be under 50 words 4. Sound like a peer engaging, not a marketer fishing Post content: [PASTE POST] Then, write the DM I should send 2-3 days later that references the comment exchange without being weird about it. Under 60 words.
Public comment → DM is the highest-converting LinkedIn path I know. Warmer than cold, less weird than InMail.
Voice note script
PROMPT 034 / 100
LinkedIn voice DMs have 5-10x reply rates vs text. Most reps don't use them.
Write a 45-60 second LinkedIn voice note script for [PROSPECT]. Context: - Prospect: [TITLE] at [COMPANY] - Specific thing I'd reference (from their profile/posts/company): [DETAIL] - My reason for reaching out: [REASON] Structure the script to be SPOKEN (not read): - Open with their name and one specific detail (5 seconds) - Main message: why I'm reaching out, said conversationally (30-40 seconds) - Close with a light ask (10 seconds) Include natural pauses (marked with "..."), and keep the language simple. Sentences should be short. No jargon. No "synergy." Write it the way I'd actually talk, not the way I'd write.
The 'how I'd talk, not how I'd write' framing is critical. Read the script out loud before recording.
The 'saw your post' warm opener
PROMPT 035 / 100
When they posted something you can actually engage with genuinely.
[PROSPECT] posted something on LinkedIn that's directly relevant to what I sell. Write a DM that references their post. Their post (paste content): [POST] What I actually think about their post (my honest take): [MY TAKE] My product: [PRODUCT] Rules: - Lead with a genuine engagement with their idea — agreement, extension, or polite pushback - Do NOT pivot to a pitch within the same message - End with a question that continues the conversation about THEIR idea, not mine - Under 70 words Save the product mention for the next message, after they reply.
The 'save the product mention for next message' rule is what separates this from spam. Most people break it immediately.
Re-engagement after they ghosted
PROMPT 036 / 100
Pick a stalled LinkedIn conversation back up without awkwardness.
I had a LinkedIn conversation with [PROSPECT] that went quiet [N] weeks ago. Here's the last message I sent: [PASTE LAST MESSAGE] Write a re-engagement DM that: - Doesn't reference the silence - Doesn't apologize - Opens with something new (news, a relevant idea, a question) - Gives them a frictionless way back into the conversation - Doesn't make it feel like I've been waiting by the phone Under 60 words.
'Doesn't make it feel like I've been waiting by the phone' is the tone you want. Casual. Unattached. It converts better.
InMail for people not in your network
PROMPT 037 / 100
The rules are different for paid reaches. More room, but higher expectations.
Write a LinkedIn InMail for [PROSPECT] I'm not connected to. Context: - Prospect: [NAME, TITLE, COMPANY] - My specific observation about them or their company: [OBSERVATION] - My product: [PRODUCT] - The ask: [ASK] Rules: - InMails can be longer than connection requests, but still under 150 words - Subject line should reference something specific to them (not my product) - Body should feel effortful (like I actually did research) - The ask should match the depth of research — don't do 3 hours of research and then ask for "15 mins" Give me the subject line and the body.
The 'ask should match the depth of research' note is a useful rule to internalize generally. Effort asymmetry kills deals.
Engagement-bait post to attract the buyer
PROMPT 038 / 100
Post content that makes your ICP come to YOU.
Write a LinkedIn post designed to attract engagement from [ICP — specific title/industry]. My goal: get people from [ICP] to comment, which I can follow up on as a softer outreach. Topic: [TOPIC THAT IS PAIN-ADJACENT FOR ICP] My point of view on it (unpopular or at least not-widely-said): [POV] Post structure: - Line 1: a specific claim or observation (not a question) - Lines 2-5: why I think this, told through a story or a concrete example - Line 6: one sentence that invites disagreement or addition - Line 7: no question, no "what do you think?" — let it land Under 150 words. Punchy line breaks. No hashtags.
The 'no what do you think?' rule works because it dodges the classic pattern everyone ignores. Silence invites better replies.
DM after they engage with your post
PROMPT 039 / 100
They liked or commented on your post. Now what?
[PROSPECT] just [liked / commented on] my LinkedIn post. Write a DM I can send them that converts this engagement into a conversation. Context: - Their engagement (paste comment if applicable): [ENGAGEMENT] - My post topic: [TOPIC] - My product: [PRODUCT] Rules: - Lead by genuinely engaging with what THEY did, not thanking them for engagement - Ask a question that extends the topic of the post - Don't pitch in this message - Under 50 words Separate it from a generic "thanks for the like" DM. This should feel like a continuation of the idea, not a sales trigger.
The 'don't thank them for the like' is surprisingly hard for people. It's the single most common mistake.
Multi-step LinkedIn sequence (5 touches)
PROMPT 040 / 100
The full DM cadence laid out, not just individual messages.
Build a 5-step LinkedIn outreach sequence over 21 days. Prospect: [TITLE] at [COMPANY] My product: [PRODUCT] Research/hook I have: [HOOK] For each step, give me: - Day number - Channel (connection request, DM, comment on their post, voice note, etc.) - Full message copy - Purpose of this step (what am I trying to learn or earn?) Rules: - No single step can pitch the product directly - Must include at least one non-DM touch (comment, reaction, etc.) - Step 5 is a breakup / "OK to close the loop" message - Full sequence under 500 words Don't optimize for volume. Optimize for the prospect feeling like a human is doing this.
'Optimize for the prospect feeling like a human is doing this' is the whole prompt. Set that and the rest falls into place.
05
Discovery Call Prep
Everything you do before the call has a bigger impact on the outcome than anything you do in it.
One-page pre-call brief
PROMPT 041 / 100
Everything you need on one screen before the call starts.
Generate a one-page pre-call brief for [PROSPECT NAME] at [COMPANY], who I'm meeting at [TIME] on [DATE]. My product: [PRODUCT] Deal size estimate: [$X] Stage: [DISCOVERY / 2ND CALL / ETC.] Include these exact sections: 1. WHO (one sentence on them personally — role, tenure, LinkedIn-visible priorities) 2. WHAT (three sentences on the company — what they do, recent changes, buying signals) 3. WHY (my best guess at why they took this call — phrased as their motivation, not mine) 4. RISKS (what could tank this deal or conversation — 2-3 items) 5. GOAL (one single sentence on what a "good outcome" of this specific call looks like) Keep it under 300 words total. If you don't have information for a section, say "UNKNOWN — investigate before call." Don't fabricate.
The single-sentence GOAL forces clarity. Most reps go into discovery calls wanting 5 things and getting none.
Discovery question bank (custom to them)
PROMPT 042 / 100
15-20 discovery questions personalized to this specific deal.
Generate 15-20 discovery questions tailored to [PROSPECT + COMPANY]. Context: - Prospect: [TITLE] at [COMPANY] - My product: [PRODUCT] - What I already know: [CONTEXT] - What I most need to learn: [UNKNOWNS] Organize the questions into 4 groups: 1. CURRENT STATE (how they operate today) 2. PAIN & PRIORITY (what's broken, how much it hurts) 3. DECISION PROCESS (who, how, by when, budget) 4. FUTURE STATE (what does "good" look like to them) For each question: - Avoid "what keeps you up at night" and similar cliches - Make it specific to what they'd actually be dealing with in their role - Phrase it as you'd actually ask it — conversational, not interview-y Add one "unexpected" question at the end that might surface something their answers otherwise wouldn't.
The 'unexpected' question at the end is often the one that moves the deal. It's the one they haven't rehearsed an answer to.
Likely-objection preview
PROMPT 043 / 100
Know what's coming before it comes.
Based on what you know about [COMPANY] and [PROSPECT TITLE], predict the top 4 objections I'm likely to hear on this call. My product: [PRODUCT] Price point: [$X] Known context: [CONTEXT] For each predicted objection: - State it in the exact language they'd likely use (not a softened version) - Rate likelihood: HIGH / MEDIUM / LOW - Underlying concern it represents (the real thing behind the stated objection) - The best response — not a rebuttal, a response - The question I should ask them before responding to get more context Order by likelihood.
'Response, not a rebuttal' is the distinction to internalize. Rebuttals make them defensive. Responses invite more information.
Stakeholder map from scratch
PROMPT 044 / 100
Figure out who actually needs to be in the room before the room forms.
For a deal with [COMPANY] on [PRODUCT], map the likely stakeholders. Deal size: [$X] Known contact: [NAME, TITLE] For each stakeholder, give me: - Title and likely seniority - Role in the decision: CHAMPION / INFLUENCER / BUYER / USER / BLOCKER / UNKNOWN - What they individually care about (their personal incentive, not the company's) - What they might try to kill or slow this deal - The best way to win them over (or neutralize them) Include anyone from: the champion's team, finance/procurement, IT/security, legal, end-users, and exec sponsor. Flag any stakeholder role that's suspiciously absent from my current view of this deal.
The 'flag suspiciously absent stakeholders' line is what turns a map into actionable intelligence. Missing a stakeholder is how deals die.
Mutual-interest hook generator
PROMPT 045 / 100
Find 2-3 non-business things you might genuinely connect over.
Based on [PROSPECT]'s LinkedIn profile and public presence, give me 2-3 non-business things we might genuinely connect over at the start of a call. Profile/context: [PASTE PROFILE OR CONTEXT] For each connection point: - What it is - Why it's genuine (NOT "we both went to business school") - How to bring it up naturally in the first 2 minutes of a call - Red flag: any topic to AVOID (politics, current events, anything risky) If there's nothing genuinely worth connecting over, tell me that. Small talk is better than forced small talk.
The 'small talk beats forced small talk' line is correct. Don't force connection points that aren't there.
Agenda proposal for the meeting
PROMPT 046 / 100
A written agenda you send before the call that sets the frame.
Write an agenda for a [LENGTH]-minute discovery call with [PROSPECT] at [COMPANY] that I can send in the calendar invite. Context: - My product: [PRODUCT] - My stated goal for the call: [GOAL] - Their likely goal: [THEIR GOAL] - Stage: [FIRST CALL / FOLLOW-UP / ETC.] The agenda should: - Open with their context, not mine (5 min) - Include a specific question I want to explore, not generic "learn about your business" - Make room for their questions explicitly (last 5 min) - Set clear expectations about what this call will and won't do - Feel collaborative, not prescribed Include a short paragraph before the agenda explaining why I structured it this way.
Sending a written agenda pre-call signals seniority and intent. Most reps don't do it. Those who do get taken more seriously.
Competitor battlecard (specific to this deal)
PROMPT 047 / 100
Which competitor is likely in the room? What's your angle?
Based on the context below, predict which competitor is most likely to be in this deal — or which alternative the prospect is considering. Company: [COMPANY] Product I sell: [PRODUCT] Signals I've seen: [SIGNALS] Known stack: [STACK if known] For the most likely competitor: - Their likely pitch to [PROSPECT] - Their genuine strengths (not strawman versions) - Their genuine weaknesses - The ONE question to ask the prospect that reveals whether competitor is actively in deal - How I should position WITHOUT trashing the competitor Also: if the most likely alternative is "do nothing" or "build in-house," tell me that. Status quo wins more deals than competitors.
The 'status quo wins more deals than competitors' reframe is right. Most battlecards ignore the biggest competitor: inertia.
Reverse agenda: what they want from ME
PROMPT 048 / 100
Flip the discovery — prepare to answer, not just ask.
Most discovery call prep is about what I want to learn from [PROSPECT]. Flip it. What are the top 5 things [PROSPECT] probably wants to learn from ME on this call? Context: - Prospect: [TITLE] at [COMPANY] - My product: [PRODUCT] - Where we are in the process: [STAGE] For each thing they want to learn: - The question they'll likely ask (in their words) - Why they're asking it — the real concern behind the question - The best way to answer it — honest, specific, brief - The worst way to answer it (the mistake most reps make) Rank by likelihood of coming up.
Preparing to answer is harder than preparing to ask. Most reps skip it. This is the advantage.
Demo flow blueprint
PROMPT 049 / 100
Design the demo before building it.
Build a custom demo blueprint for [PROSPECT] at [COMPANY] based on what I know about them. Context: - Their likely workflow today: [CURRENT STATE] - The pain point I most want to spike: [PAIN] - Their likely objections: [OBJECTIONS] - My product: [PRODUCT] - Demo length: [LENGTH] Build: 1. Opening frame (30 sec) — what the demo will prove, in their language 2. Three "wow" moments (the specific product actions that spike their pain) 3. One pre-empted objection (show the answer before they ask) 4. Closing question (not "what do you think?" — specific and directional) For each moment, give me: - The exact click-path / scenario - What I should say while doing it - What I should NOT show (features that aren't relevant)
'What NOT to show' is the most undervalued demo skill. Cutting features out improves close rates more than adding them.
First-90-seconds script
PROMPT 050 / 100
Scripted opening; unscripted from minute two onward.
Write the first 90 seconds of a discovery call with [PROSPECT]. This is the only part I want scripted. After 90 seconds we go unscripted. Context: - Prospect: [NAME, TITLE] - Me: [MY NAME, ROLE] - How we got here: [CONNECTION — cold outreach reply / inbound / intro] - My stated goal for the call: [GOAL] Structure: - Seconds 0-15: greeting + one-line rapport - Seconds 15-45: frame what the call is (and isn't) - Seconds 45-75: one opening question that invites them to talk - Seconds 75-90: pause. Let them talk. Write the ACTUAL words I'll say. Conversational. Not corporate. Not a sales script.
The 'pause. Let them talk.' instruction is the whole trick. Most reps talk for 3 minutes and lose the room.
Halfway through
These are the free 100. The paid 50 are agents.
Prompts are single-purpose. Agents are workflows, they run end-to-end, remember context, and connect to your stack.
The call ended. Now the real work starts: extract the signal, write the notes, build the next move.
Call transcript → next-action brief
PROMPT 051 / 100
Paste a Gong/Fireflies transcript, get a clear action brief.
Below is a transcript of a call I just had with [PROSPECT] at [COMPANY]. [PASTE TRANSCRIPT] Produce a structured brief: 1. KEY MOMENTS — the 3 most important things they said (quote directly + timestamp if available) 2. PAIN SIGNALS — what they're actually trying to solve, in their words 3. OBJECTIONS — what they objected to or seemed hesitant about 4. COMMITMENTS — what I explicitly or implicitly promised them 5. NEXT ACTION — the single most important thing I need to do in the next 48 hours, with a specific ownership 6. RED FLAGS — anything that worries you about this deal Keep each section under 60 words. Give me the signal, not the story.
'Signal, not the story' is the prompt instruction that stops AI from narrating the whole call back to you.
MEDDPICC scoring from call notes
PROMPT 052 / 100
Fill MEDDPICC / your qualification framework from raw notes.
Based on the call notes below, score this deal against MEDDPICC. For each dimension, give me: - SCORE: 1-5 (1 = completely unknown, 5 = fully confirmed with evidence) - EVIDENCE: the specific thing from the notes supporting the score - GAP: what I still don't know Notes: [PASTE NOTES] Dimensions: - M: Metrics (quantified pain) - E: Economic buyer (who signs) - D: Decision criteria - D: Decision process - P: Paper process (legal, procurement) - I: Identified pain - C: Champion - C: Competition At the end, tell me the biggest gap and the ONE discovery question that would close it.
The 'biggest gap + one question' constraint at the end is the thing. Otherwise MEDDPICC becomes a ritual, not a tool.
Post-call follow-up email
PROMPT 053 / 100
The written recap that demonstrates you listened.
Write a post-call follow-up email to [PROSPECT] based on the notes below. Call notes: [PASTE NOTES] Structure: 1. Thank them briefly (one line, not effusive) 2. Recap — bullet-style — what I heard about their situation (NOT what I said) 3. Confirm the next step with a specific date/time if we agreed on one 4. Attach/link the ONE most useful resource that's relevant to something specific they said Rules: - The recap should be in THEIR language, quoting where possible - Don't editorialize or reframe their pain in my product's language - Under 150 words total Tone: a peer who took good notes, not a rep executing a playbook.
Recapping in their language (not yours) is the single biggest differentiator. Most reps recap by restating the pitch.
Champion-test email
PROMPT 054 / 100
Test whether your 'champion' is actually a champion.
Write a follow-up to [CHAMPION] asking them to do something that will reveal whether they're a real champion or just a friendly contact. Context: - Champion: [NAME, TITLE] - Deal stage: [STAGE] - The "ask" that tests championship: [SPECIFIC ACTION — e.g., "introduce me to [ECONOMIC BUYER]", "review and share this one-pager internally", "confirm the business case we discussed"] Rules: - The ask should be concrete and time-bound (not "let me know when you have time") - Frame it as mutual — I'm asking because I want to give them something useful to share, not because I need them to carry water - Make it easy to say yes, but also easy to say "actually I'm not the right person" — that's useful intel too - Under 100 words
The 'easy to say not the right person' out is the real magic. Fake champions take the out. Real ones don't.
Objection lookback (what I missed)
PROMPT 055 / 100
Review a call where the deal slipped and identify what you missed.
Here's the transcript or notes from a call where the deal seems to be slipping: [PASTE] Analyze where I went wrong: 1. MOMENTS I MISSED — 3 places where the prospect gave a signal I didn't pick up 2. QUESTIONS I SHOULD HAVE ASKED — questions that would have surfaced real concerns 3. THINGS I SAID THAT WERE WRONG — where I pitched when I should have listened, or assumed when I should have asked 4. WHAT TO DO NOW — a specific recovery move, not "send a follow-up email" Be direct. I want useful criticism, not encouragement.
'I want useful criticism, not encouragement' forces the model out of its default reassurance mode. Huge difference.
Multi-call thread summary
PROMPT 056 / 100
Summarize everything across 3+ calls into a single deal narrative.
I've had [N] calls with [PROSPECT] at [COMPANY]. Below are the notes from all of them. [PASTE ALL NOTES] Build me a single deal narrative: 1. WHERE WE STARTED — the original pain they articulated (call 1) 2. HOW IT'S EVOLVED — what's changed in their articulation across calls 3. WHAT'S STAYED CONSTANT — the core thing they keep coming back to 4. WHO'S ENTERED THE PICTURE — any new stakeholders that have appeared 5. CURRENT STATE — what I believe is true right now vs what's still unknown 6. THE DEAL IN ONE SENTENCE — if I had to describe this deal to my manager in one sentence, it's this: Keep it under 400 words total. This is a narrative, not a list. Write it like I'll re-read it before the next call.
The single-sentence deal summary at the end is the one most sales teams skip. It's the most useful part.
Gap-to-close diagnosis
PROMPT 057 / 100
What's between you and the yes, specifically.
Based on the notes below, diagnose what's between me and closing this deal. Current stage: [STAGE] Deal size: [$X] Notes: [PASTE] Output: 1. BIGGEST GAP — the single biggest thing preventing a close right now 2. UNDERLYING CAUSE — the real reason for that gap (not the stated one) 3. WHAT NEEDS TO HAPPEN — what, specifically, needs to be true for this to close 4. MY NEXT MOVE — the single most impactful thing I can do in the next week 5. RISK — the thing that could go wrong between here and close if I'm not careful Don't give me 5 items for any section. Give me the most important one.
'Don't give me 5 items' is the forcing function. Prioritization is the whole value of this prompt.
Quote extraction for internal buy-in
PROMPT 058 / 100
Pull the prospect's own language for your sales-engineering slack thread.
Pull direct quotes from the transcript below that I can use to build internal buy-in for [DEAL]. [PASTE TRANSCRIPT] Give me quotes that support: 1. URGENCY — why this needs to happen now 2. BUSINESS VALUE — what they lose by not doing it 3. FIT — why our product specifically solves their thing 4. RISK — what could go wrong internally on their side Each quote should be direct (in quotation marks), attributed to the speaker, with timestamp if available. Don't paraphrase. Don't improve their grammar. Raw quotes only.
Raw quotes build more internal buy-in than any deck. Everyone's tired of slides; nobody's tired of the prospect's exact words.
Emotion / tone analysis
PROMPT 059 / 100
How did they REALLY feel about what you said?
Analyze the emotional tone of [PROSPECT] during the call based on the transcript below. [PASTE TRANSCRIPT] For each major topic discussed, tell me: - Their apparent emotional register (engaged, skeptical, polite-but-closed, genuinely enthusiastic, frustrated, etc.) - What in their language suggests this (cite specific phrases or tells) - How this should shape my next move Pay attention to: hedging language, shifts in energy, moments they went quiet, moments they asked follow-ups. Not just what they said but how. If you can't tell from transcript alone, say so. Don't guess.
The 'don't guess' line stops the model from over-interpreting text that has no tone. Useful humility.
Lessons-learned journal entry
PROMPT 060 / 100
End-of-day reflection that compounds over months.
Based on the call below, write a short journal entry capturing the lessons for my future calls. [PASTE CALL NOTES OR TRANSCRIPT] Structure: 1. WHAT WORKED — the one thing I did in this call that I should repeat 2. WHAT DIDN'T — the one thing I did that I should not repeat 3. WHAT I LEARNED — one insight about [THIS PROSPECT / THIS ICP / THIS PRODUCT CATEGORY] that will be useful next time 4. PATTERN TO WATCH — is this part of a trend across multiple calls? Keep it under 200 words. Write it in first person, like I'm talking to myself, not formally.
Logging lessons like this daily, for 6 months, is the single best sales development practice. Most reps don't do it.
07
Objection Handling
Most objections aren't objections. They're unfinished sentences. The right response asks the next question, not reads the rebuttal.
Translate objection → real concern
PROMPT 061 / 100
What they said vs what they actually mean.
The prospect said: "[PASTE OBJECTION]" Give me: 1. WHAT THEY LITERALLY SAID — paraphrased 2. THE 3 THINGS THEY MIGHT ACTUALLY MEAN — ranked by likelihood, with the real concern behind each 3. THE ONE QUESTION I SHOULD ASK NEXT to figure out which one is true (do not respond to the objection yet) 4. ONLY AFTER THAT — the best response for each of the 3 possible underlying concerns The question in step 3 is the most important part. Do not skip it.
'Do not respond to the objection yet' is the instruction that makes this work. Most rebuttals fail because they respond to the wrong concern.
Price objection diagnosis
PROMPT 062 / 100
"It's too expensive" means 10 different things.
The prospect said: "[PASTE PRICE OBJECTION]" Price objections usually mean one of: A) Budget doesn't exist / isn't approved B) Budget exists but not for this category C) Value isn't clear yet D) Value is clear but they're negotiating E) Comparison with a cheaper alternative F) Timing is wrong, not price G) They're testing me to see if I discount Tell me: 1. Which 2 are most likely given the context below 2. The diagnostic question for each 3. The response for each 4. Which one I should ABSOLUTELY NOT assume it is Context: [PASTE DEAL CONTEXT]
The '7 things price can mean' taxonomy is useful to have in your head permanently. Rarely is price actually about price.
Timing objection: "not right now"
PROMPT 063 / 100
"Not now" means "never" about 80% of the time. The other 20% matters.
The prospect said some version of "it's not the right time" or "let's revisit in 6 months." Context: [PASTE CONTEXT] Tell me: 1. Is this a real timing concern or a polite no? (give me 3 signals to distinguish) 2. If it's real, what's the underlying trigger event I should tie my next outreach to? 3. If it's a polite no, what's the graceful way to accept it and preserve the relationship? 4. A 6-month nurture plan that doesn't require checking in every 2 weeks (5 touches total, spaced strategically, each with a genuine reason)
'Doesn't require checking in every 2 weeks' is the key. Most nurture cadences are just slower versions of the original sequence.
Feature-gap objection
PROMPT 064 / 100
They want a feature you don't have. What now?
The prospect said: "Do you have [FEATURE]?" — and I don't. Context: - My product: [PRODUCT] - The feature they asked about: [FEATURE] - What I actually do in that area: [WORKAROUND OR ADJACENT FUNCTIONALITY] Give me: 1. The honest acknowledgment — don't pretend I have it 2. The diagnostic question to understand WHY they want that feature (often the answer reveals the underlying need is solvable another way) 3. The reframe — how I'd describe what I DO have that addresses the underlying need 4. The "when to walk away" test — at what point do I stop trying and recognize this is a genuine fit issue Rule: I will not promise a roadmap item unless it's genuinely committed. Flag any response that leans that way.
The 'I will not promise roadmap' rule is load-bearing. Roadmap promises kill more deals at renewal than they save at new business.
"We already use [competitor]" objection
PROMPT 065 / 100
Displacement isn't about why you're better. It's about why they'd switch.
The prospect said: "We already use [COMPETITOR]." Context: - My product: [PRODUCT] - Their competitor: [COMPETITOR] - Known pain with current solution (if any): [PAIN] - Deal size: [$X] Give me: 1. The question I should ask FIRST — not about my product, about their experience with [COMPETITOR] 2. The most common real reason this objection comes up (with the best response) 3. The reframe — position switching cost as lower than they think, or position the pain of staying as higher than they think. Pick one based on context. 4. The honest answer if [COMPETITOR] is genuinely a better fit — when should I recommend they stay? Don't trash the competitor. That loses deals with senior buyers.
'When should I recommend they stay' forces honesty into the prompt. The best sellers actively DQ bad-fit deals.
Stalling: "let me think about it"
PROMPT 066 / 100
The most common stall, the most mishandled.
The prospect said: "Let me think about it" or "I'll get back to you" after what seemed like a strong call. Context: [PASTE CONTEXT] This stall usually means: - They liked it but don't have authority / budget - They have a concern they didn't voice - They're being polite - They genuinely need to process Give me: 1. The ONE thing I should say in the moment to test which of these it is (without pressuring them) 2. The follow-up message to send 48 hours later that surfaces the real concern 3. Signs in their response that tell me it's dead vs still alive Rule: do not use "is there anything holding you back?" That's table stakes and they've all heard it.
Banning the question everyone uses forces a more creative prompt output. Try this technique generally.
Procurement / legal stall
PROMPT 067 / 100
The deal's done but procurement is sitting on it.
My deal is waiting on [PROCUREMENT / LEGAL] at [COMPANY]. My champion is [CHAMPION]. Context: - Time stalled: [DAYS] - What procurement has asked for so far: [ASKS] - Deal size: [$X] - End of quarter: [DATE] Tell me: 1. Is this normal pacing or actually stalled? (Give me the benchmark) 2. What can my champion do that would unstick this? 3. What can I do directly without going around my champion? 4. When is it acceptable to escalate, and to whom? 5. The specific message to send my champion right now (under 80 words) Assume procurement is a black box and act accordingly. Don't assume my champion has magic.
'Don't assume my champion has magic' is the reality check. Champions are busy too, and internal friction is real.
Security review objection
PROMPT 068 / 100
InfoSec questionnaire hell. Pre-empt or respond.
The prospect's security team has raised a concern: "[PASTE SECURITY CONCERN]" Context: - My product: [PRODUCT] - Our security posture: [RELEVANT — SOC2, ISO, GDPR, etc.] - What we do in the specific area they're concerned about: [DETAIL] Give me: 1. The plain-English translation of what they're actually worried about 2. The direct technical answer 3. The non-technical framing I can use with my champion to help them defend this internally 4. What to do if our posture DOES have a genuine gap here (don't lie, don't oversell) 5. A one-liner that buys me time to get the right answer from our security team Flag anything that should NOT be answered by me directly vs escalated to security.
Security objections are where winging it kills deals. The 'what to escalate' flag is worth having baked in.
Champion-said-no objection
PROMPT 069 / 100
When your internal advocate cools off.
My champion [NAME] has gone cold / said this deal is no longer a priority / stopped responding. Context: - Last interaction: [DETAILS] - What I THINK changed: [HYPOTHESIS] - My product: [PRODUCT] Give me: 1. The likely reasons a champion cools (ranked by frequency) 2. The one question I can ask [CHAMPION] that will surface the truth without making them defensive 3. The plan if my champion is truly dead — do I find a new champion in the same account, or walk away? 4. The message to send right now (under 75 words) Be honest if the right answer is to let this one go.
'Be honest if the right answer is to let this one go' protects your pipeline from zombie deals eating cycles.
Mass-scale objection library
PROMPT 070 / 100
Build a personal objection playbook for your specific product.
Build me a personal objection-handling library for [MY PRODUCT]. For each of the 10 most common objections my ICP raises: 1. The exact phrasing I'd hear (not a softened version) 2. What it usually really means 3. The diagnostic question to ask before responding 4. The best response (30-50 words) 5. A case study or data point I can cite 6. When to accept the objection and walk ICP context: [ICP DESCRIPTION] My product: [PRODUCT] Price point: [$X] Format as a lookup table I can reference in real-time during calls.
Build this once, refine quarterly. The compounding benefit over 12 months is massive.
08
Proposal & Pitch
The proposal is not the pitch. The pitch is what the champion tells people in the elevator when you're not there.
One-page proposal from scratch
PROMPT 071 / 100
The full proposal on a single page, nothing wasted.
Write a one-page proposal for [PROSPECT] at [COMPANY]. Inputs: - Their stated problem: [PROBLEM] - What they've told me matters most: [PRIORITIES] - My proposed solution: [SOLUTION] - Investment: [$X] - Timeline: [TIMELINE] Structure (in this exact order): 1. THE SITUATION — their current state, in their words (3 lines) 2. THE COMPLICATION — what happens if they don't act (2 lines) 3. THE PROPOSAL — what I'm proposing, specific and scoped (4 lines) 4. THE OUTCOME — what changes in their business (3 bullet points, quantified where possible) 5. THE INVESTMENT — price + what's included, no hidden fees (2 lines) 6. THE NEXT STEP — exactly what they do next Keep total under 350 words. No "we are thrilled to propose." No "in today's fast-paced landscape." Write it like I'd talk.
The Situation/Complication/Proposal structure is McKinsey's 'minto pyramid.' It's boring because it works.
ROI / business case builder
PROMPT 072 / 100
Translate features into financial impact they can defend internally.
Build a business case for [PROSPECT] that my champion can defend internally without me in the room. Context: - Their current state cost (time, money, risk): [CURRENT COST] - My product's impact (time saved, revenue unlocked, risk reduced): [IMPACT] - My price: [$X] - Their company size / revenue: [SIZE] Build: 1. The "cost of doing nothing" in dollars, over 12 months (show the math) 2. The expected outcome from implementing, in dollars, conservatively 3. The ROI ratio, payback period, and net benefit 4. The 2-3 assumptions this rests on (state them plainly — if any break, the case breaks) 5. The "what would make this case stronger" — what additional data would make this undeniable? Don't inflate. I want a business case my champion's CFO won't mock.
'A business case my champion's CFO won't mock' is the standard. Inflated ROI kills more deals than it wins.
Scope-of-work (SOW) generator
PROMPT 073 / 100
The commercial scope, not the marketing pitch.
Generate a scope of work for [PROSPECT]. Inputs: - What they're buying: [PRODUCT / SERVICE] - Commercial model: [SUBSCRIPTION / PROJECT / RETAINER / HYBRID] - Fee: [$X] - Term: [TERM] Sections: 1. DELIVERABLES — specific, countable, finished-state descriptions (not "help with marketing" — "X emails per month, Y landing pages, Z reports") 2. IN-SCOPE — what's included 3. OUT-OF-SCOPE — what's NOT included (this is often more important than #2) 4. ASSUMPTIONS — what needs to be true on their side for this to work 5. CHANGE CONTROL — how we handle additions 6. SUCCESS METRICS — what we're measured against 7. TIMELINE & DEPENDENCIES — key milestones, plus what THEY owe us and when Flag any part that's vague enough to cause a scope dispute later. Don't write a proposal; write a contract-adjacent doc.
The 'out-of-scope' section is what separates amateur SOWs from professional ones. Be ruthless about listing what you WON'T do.
Three-option pricing page
PROMPT 074 / 100
Good/better/best framing with the middle option engineered to win.
Build a 3-option pricing page for [PROSPECT]. Context: - Target deal: [$X — I want this to be the middle option] - Their pain: [PAIN] - My product capabilities: [CAPABILITIES] Build three tiers: - MINIMUM (solves the pain but with obvious trade-offs) - RECOMMENDED (the one I want them to pick — priced at [$X]) - PREMIUM (looks great, includes extras they probably don't need) For each tier: - Name (not "Bronze/Silver/Gold" — something that fits their vocabulary) - Price - Inclusions (3-5 bullets) - One key exclusion that makes the upgrade obvious - A one-liner on "who this is for" Engineer the middle option so it's the obvious choice. The minimum should feel thin; the premium should feel like more than they need.
Three-option pricing is decision architecture. Without a premium anchor, the 'recommended' tier feels expensive.
Proposal email that doesn't suck
PROMPT 075 / 100
The email that carries the proposal. Most reps botch this.
Write the email that accompanies my proposal to [PROSPECT]. Inputs: - What I'm attaching: [PROPOSAL NAME] - Key number I want them to see: [NUMBER] - Main business outcome: [OUTCOME] - Deadline or urgency: [DEADLINE] Rules for this email: - Under 120 words total - DO summarize the proposal in 2-3 sentences (most people won't open the attachment first) - DO include the key number in the body - DO make the next step explicit and easy - DO NOT write "Please find attached" - DO NOT recap everything we already discussed - DO NOT start with "Thank you for your time" The email is the proposal's top-of-funnel. Treat it like a cold email: it has to earn the click to open the attachment.
'The email is the proposal's top-of-funnel' reframe is useful. Most reps treat the email as a formality. It's not.
Pitch deck from scratch
PROMPT 076 / 100
The 10-12 slide deck for an in-person or Zoom pitch.
Build a 10-12 slide pitch deck for [PROSPECT] at [COMPANY]. Inputs: - Audience: [WHO'S IN THE ROOM] - My product: [PRODUCT] - Their situation: [CONTEXT] - What I most need to prove: [PROOF POINT] Slide-by-slide outline: 1. A title slide that is NOT my logo and their logo 2. Their world today (in their words, not mine) 3. The specific cost of their current state 4. The opportunity if that state changes 5. What would have to be true for that to happen 6. How [MY PRODUCT] uniquely does that (the ONE thing, not features) 7. Proof — the most relevant case study, quantified 8. What implementation actually looks like (the reality, not the sales version) 9. Commercial — simple, three options or one clear price 10. Risks & what could go wrong (proactively addressed) 11. Next step (specific, dated) For each slide, give me: the headline, the body, and the speaker notes (what I'll actually SAY — under 40 seconds per slide).
Slide 10 (risks) is what senior buyers will remember. Pre-empting is disarming; hiding is a tell.
Executive summary for a CFO
PROMPT 077 / 100
One page. No jargon. CFO-reader-friendly.
Write a one-page executive summary for [COMPANY]'s CFO or finance approver. Context: - What I'm selling: [PRODUCT] - Price: [$X] - Term: [TERM] - Business case (from my earlier work): [SUMMARY] Rules: - CFOs don't care about features. They care about: payback period, risk of not doing it, risk of the vendor failing, and what this does to their P&L - Must fit on one page (under 350 words) - Must include: the ask, the ROI, the payback, the risk, the mitigation, the decision deadline - Must NOT include: marketing language, "transformative," "game-changing," or any superlatives - Tone: a peer who respects their time, not a salesperson Format it so a CFO can skim in 60 seconds and understand everything.
CFOs respond to respect for their time. Superlatives trigger eye-rolls. Plain numbers build trust.
The counter-proposal to their RFP
PROMPT 078 / 100
When they send an RFP that's the wrong shape, reframe it.
[PROSPECT] sent me an RFP that is asking the wrong questions / structured in a way that favors the wrong answer. I want to respond in a way that subtly reframes without being combative. Their RFP (paste or summarize): [RFP] What they should actually be asking / optimizing for: [BETTER FRAMING] My product: [PRODUCT] Give me: 1. A cover letter (under 300 words) that thanks them for the RFP, answers their questions faithfully, AND offers an alternative frame "for consideration" 2. The 3 sections in my response where I'll plant the reframe — with exact wording 3. The one question I'll ask at the end that tests whether they're open to rethinking the RFP Rules: do not ignore their questions. Do answer them. Then reframe.
The 'don't ignore the RFP' discipline is hard. Reps often go rogue and get disqualified. Answer the form. THEN plant the seed.
Multi-year commercial structure
PROMPT 079 / 100
Structure a 2-3 year deal with ramp and expansion baked in.
Build a multi-year commercial structure for [PROSPECT]. Context: - Year 1 scope and price target: [Y1 SCOPE, $X] - Expected Year 2 expansion: [Y2 SCOPE / PRODUCT SET] - Expected Year 3 state: [Y3] - Their budgeting cycle: [CYCLE] Design: 1. Year 1 structure (ramp-appropriate — they shouldn't feel over-bought) 2. Year 2 auto-expansion (triggers for upgrade based on usage / success metrics) 3. Year 3 steady state 4. Built-in protection for me: price uplift, usage floors, auto-renewal 5. Built-in protection for them: caps, out clauses for failure, pause rights 6. How I'd pitch this as BETTER for them than a 1-year deal Make this feel collaborative, not predatory. Multi-year deals win when both sides see a genuine reason for the structure.
Multi-year deals die when the rep pushes it for commission reasons. They close when the structure is genuinely mutual.
Proposal redlining / negotiation prep
PROMPT 080 / 100
They came back with edits. Prepare the response.
The prospect sent redlines on my proposal. Here's what they changed: [PASTE REDLINES OR BULLET THE CHANGES] For each redline, tell me: 1. What they changed and how 2. What that change tells me about their real concerns 3. Whether I should accept, negotiate, or reject — with reasoning 4. If I negotiate: the specific counter, and the business reason for it (not "because my manager says so") 5. The order I should address these in when I respond (don't just go top to bottom) Flag any change that's a procurement-language trap (indemnification, auto-renewal, uncapped liability) and mark as LEGAL REVIEW required.
Procurement-language traps are where reps give away margin they don't know they're giving. The LEGAL REVIEW flag is not optional.
09
Negotiation & Closing
Negotiation isn't about discounting. It's about trading. Every ask has a price; every concession has a return. Reps who forget this leave money on the table every single deal.
Discount request response
PROMPT 081 / 100
They asked for 20% off. Don't just say yes, don't just say no.
The prospect asked for [DISCOUNT REQUEST — e.g., "20% off"]. Context: - Deal: [DEAL DETAILS] - Price: [$X] - Stage: [STAGE] - Their stated reason for the discount: [REASON] Give me: 1. The one question to ask BEFORE responding (what's the real driver?) 2. Three possible responses, each trading value for value: - A: Accept a smaller discount in exchange for something (longer term, upfront payment, case study, expansion commitment) - B: Hold the price but add/remove something non-price (scope, timing, support level) - C: Walk — decline and offer a lower-tier alternative 3. For each response, the script I'd actually say 4. Which I should lead with given the context Rule: never discount without trading. Every concession earns a return.
'Never discount without trading' is the whole negotiation training distilled. Apply it religiously.
End-of-quarter close push
PROMPT 082 / 100
Create genuine urgency without manufactured pressure.
I need to close [DEAL] by [DATE] (end of quarter). It's at [STAGE]. Context: - What's still outstanding: [BLOCKERS] - My leverage: [LEVERAGE — e.g., quarter-end discount, limited implementation slots, etc.] - Their stated urgency (or lack of): [URGENCY] Give me: 1. The honest assessment — can this actually close by [DATE], or am I kidding myself? 2. If yes: the specific 3-step plan this week (with owners and deadlines) 3. The message to the champion that creates real urgency without manufactured pressure 4. The fallback — a smaller Y1 / faster close that still books revenue this quarter 5. What to NOT do (common end-of-quarter mistakes that kill relationships) Be honest. If the deal shouldn't close this quarter, tell me.
The 'should this close this quarter, or am I kidding myself' check is what most reps skip. Forecast discipline starts here.
Mutual action plan (MAP)
PROMPT 083 / 100
Jointly-owned close plan that holds both sides accountable.
Build a mutual action plan for [DEAL]. Context: - Target close date: [DATE] - Current state: [STATE] - Their key stakeholders: [STAKEHOLDERS] - My key tasks: [TASKS] - Their key tasks: [TASKS] Build a week-by-week MAP that: - Assigns ownership to every item (them or me) - Includes key checkpoints with their stakeholders (procurement, legal, exec) - Includes my support tasks (references, demos, technical calls) - Flags dependencies — what must be true before the next step - Has decision points — "by [DATE] we will have [DECISION]" Format for a shared Google Doc. Write it as collaborative, not as "here's what YOU need to do." Tone: peer-to-peer project plan.
MAPs die when they feel like sales-manufactured pressure. They work when they feel like joint project management.
Procurement negotiation script
PROMPT 084 / 100
The call with procurement — different game than the call with your champion.
I have a negotiation call with [PROSPECT]'s procurement team. My champion won't be in the room. Context: - Deal size: [$X] - What procurement has asked for so far: [ASKS] - My floor (the lowest I can actually go): [$Y] - What I want in return for any concession: [TRADES] Build: 1. The opening 2 minutes (set the tone — cooperative, not adversarial) 2. The 3 asks they'll likely make and my response to each 3. The 3 things I can give without hurting the deal (discount, term, scope) 4. The 3 things I absolutely won't give 5. The "walk away" script if they push past my floor 6. The close — how I wrap the call with clarity on next steps Rule: procurement tests me. They'll walk me up to my floor and see if I break. Decide the floor now, hold it on the call.
Deciding the floor BEFORE the call is everything. Mid-call floor-setting is how reps lose margin. Write it down first.
The "we need to think about it" at close stage
PROMPT 085 / 100
Late-stage hesitation is different from early-stage stall.
The prospect said "we need to think about it" at the close stage — not early discovery. The proposal is on the table. Context: - Stage: [LATE STAGE / VERBAL YES WAS CLOSE] - Outstanding concerns (that I know of): [CONCERNS] - Relationship strength: [STRONG / MEDIUM / WEAK] Give me: 1. The reframe — at THIS stage, "think about it" usually means something specific. What are the 3 most likely meanings? 2. The one question to ask that surfaces the real reason (not "what's holding you back") 3. The follow-up move 24 hours later 4. The question to my champion that reveals what I don't see Rule: don't panic-discount. Don't panic-add scope. Diagnose first.
The 'don't panic' rule. Late-stage hesitation feels catastrophic but it's usually information, not doom.
Closing question arsenal
PROMPT 086 / 100
Ten ways to ask for the close, not just "so are we good?"
Generate 10 different closing questions I can use depending on the situation. For each closing question: - The exact phrasing (conversational, not corporate) - The situation it works best in (e.g., "champion is ready but hasn't pulled the trigger") - The situation to AVOID it in - What to do if they say "let me get back to you" Range from the soft ("what would it take for you to feel confident moving forward?") to the direct ("should we send the paperwork this week?") to the creative ("on a scale of 1-10, how ready are you? anything under 8, what's the gap?"). Rule: no "time-to-close" questions that feel manipulative. The goal is clarity, not pressure.
The 1-10 question is the most underrated closing question in B2B sales. Low friction, high information.
Concession trade matrix
PROMPT 087 / 100
When they ask for X, what do you ask for in return?
Build a concession trade matrix for [DEAL]. If they ask for: - Discount (5%, 10%, 20%) - Extended payment terms - Shorter commitment - More features / expanded scope - Faster timeline - Custom SLA - Free pilot - Free training - Free integration support For each ask, give me: - What I would trade it FOR (longer term, case study, reference, expansion commitment, upfront payment, etc.) - The script for proposing the trade - The fallback trade if they reject the first - When to walk Output as a lookup table I can reference in real-time on calls.
Have this ready BEFORE the call. Mid-call trade invention is where reps give away value they don't realize.
Exec sponsor escalation
PROMPT 088 / 100
Your exec calling their exec — done right.
I need my exec sponsor to reach out to [THEIR EXEC] to unstick [DEAL]. Context: - My exec: [NAME, TITLE] - Their exec: [NAME, TITLE] - What's stuck: [BLOCKER] - What a successful outreach looks like: [OUTCOME] Build: 1. The briefing I give my exec (under 150 words) 2. The email my exec would send their exec (under 100 words, written in my exec's voice — senior, strategic, not tactical) 3. What my exec should do if they get a positive reply 4. What my exec should NOT do (common exec mistakes — going too tactical, going too soft, etc.) 5. My follow-up after the exec-to-exec happens Rule: exec sponsor plays work once per deal. Don't burn the card on something small.
'Exec cards play once per deal' is the constraint that makes them valuable. Over-use devalues the escalation.
The "final offer" email
PROMPT 089 / 100
When negotiation is dragging and you need to force the close.
Write the "final offer" email to [PROSPECT]. Context: - Negotiation length so far: [WEEKS] - Where we've landed: [CURRENT TERMS] - The final terms I'm willing to do: [TERMS] - The deadline: [DATE] Rules for this email: - Must be genuinely final. Do not send if I'm willing to budge further. Credibility once broken is hard to rebuild. - State the terms clearly - State the deadline - State what happens if no response (the offer expires, not a threat but a fact) - Keep the door open warmly if they walk - Under 150 words Tone: firm but not hostile. "This is my best offer and I'm at peace with either outcome."
'At peace with either outcome' is the mindset that makes 'final' actually final. If you're not at peace, don't send.
Post-close handoff template
PROMPT 090 / 100
Deal won. Don't lose the customer in the first 30 days.
Deal with [CUSTOMER] just closed. Build the internal handoff document for [CS/IMPLEMENTATION TEAM]. Context: - Deal: [PRODUCT, $X, TERM] - Key stakeholders: [NAMES, ROLES] - What they bought and WHY: [USE CASE] - What they expect (stated): [EXPECTATIONS] - What I promised (even informally): [PROMISES] - Their "success" definition: [SUCCESS] Include: 1. Background & context (under 200 words) 2. Stakeholder map with who to involve when 3. Promises I made (separated into "contractual" vs "verbal") 4. Red flags and risks 5. First 30 days — what must happen for them to feel good 6. Where they're most likely to churn if we don't nail onboarding 7. How I want to stay involved (and how I don't) Write this assuming the CS team has never spoken to me.
The 'verbal promises' section is what prevents the worst customer-success fights. Write them down BEFORE handoff.
10
Post-Sale & Expansion
The closed deal is the smallest deal you'll do with this customer. The expansion — if you earn it — is where the real revenue lives.
Kickoff meeting script
PROMPT 091 / 100
Set the relationship tone in the first 30 minutes.
Write the full kickoff meeting script for [CUSTOMER]. Context: - What they bought: [PRODUCT] - Their stakeholders: [NAMES, ROLES] - Expected timeline: [TIMELINE] - Their "success" definition: [SUCCESS] Structure the 45-minute meeting: 1. Opening 5 min: reset context, confirm people, set expectations for this call 2. 10 min: what does success look like — walk through what we agreed on, confirm or adjust 3. 10 min: what could go wrong — risks, dependencies, who owns what 4. 10 min: the 30/60/90 day plan — specific milestones 5. 5 min: communication cadence — how we'll work together 6. 5 min: wrap + next meeting For each section, give me the actual words I'll say, plus the one question I'll ask. Conversational tone, not corporate. Like a peer-to-peer project kickoff, not a welcome ceremony.
'Peer-to-peer project kickoff, not welcome ceremony' is the tone you want. No cheerleading. All professionalism.
Expansion opportunity detector
PROMPT 092 / 100
Read the room — when is the customer ready for more?
Analyze the notes below from [CUSTOMER] and tell me where the expansion opportunities are. Context: - Current spend: [$X] - Current products/services: [CURRENT] - Time as customer: [TENURE] - Relationship strength: [STRENGTH] Recent notes / signals: [PASTE] For each potential expansion: - The signal that suggests it (specific, from notes) - The expansion product / service that maps to it - The estimated expansion value: small, medium, large - The right moment to bring it up - The right person to bring it up to (me, or CS, or both) - The risk if I bring it up too early Rank by readiness. Flag anything that suggests I should NOT bring up expansion right now (e.g., they're struggling).
The 'don't bring it up if they're struggling' filter is what separates good AMs from pushy ones.
Renewal risk assessment
PROMPT 093 / 100
90 days out from renewal, what's the honest read?
We're [DAYS OUT] from [CUSTOMER]'s renewal. Give me an honest risk assessment. Context: - Contract value: [$X] - Usage trend over last 90 days: [TREND] - Recent interactions / sentiment: [SENTIMENT] - Known changes in their business (new exec, budget cuts, etc.): [CHANGES] Output: 1. Renewal risk level: GREEN / YELLOW / RED (with the honest reasoning) 2. The signals that drove that rating 3. The 3 specific actions I should take in the next 30 days to reduce risk 4. The conversation to have now (not at renewal), with script 5. Price / term strategy: should I push to expand, hold, or expect a downgrade? Be direct. If this is going to churn, tell me now so I can act, not in week -2.
Early honest reads save renewals. Late optimistic reads lose them. The GREEN/YELLOW/RED call forces the issue.
Referral request script
PROMPT 094 / 100
Ask for a referral without being weird.
I want to ask [CUSTOMER] for a referral. They're a strong, happy customer. Context: - Relationship: [RELATIONSHIP] - Recent success they had with us: [SUCCESS] - What I'd ideally want: [ASK — intro, recommendation, quote, etc.] Write: 1. The script for asking in-person or on a call 2. The follow-up email after a verbal yes 3. The specific "I'd ideally love an intro to [PERSON/COMPANY/TYPE]" phrasing that makes it easy for them 4. The reciprocity I'll offer (what I do FOR them in return) 5. The graceful exit if they say no Rules: don't make them do work. The whole ask should take them under 5 minutes to execute.
'Under 5 minutes to execute' is the discipline. Referral asks fail when they require the customer to draft the intro.
QBR (Quarterly Business Review) prep
PROMPT 095 / 100
The QBR that actually matters, not a recap slideshow.
Build the agenda for a QBR with [CUSTOMER]. Context: - Contract: [DETAILS] - What's gone well: [WINS] - What hasn't: [ISSUES] - Their priorities for next quarter: [PRIORITIES] Rules for the QBR: - Not a status report. Not a features update. - Built around THEIR business, not my product - Must have: a clear decision or direction coming out of the meeting - Must include: what's not working (avoiding this erodes trust) - Must include: expansion opportunity framed around their roadmap, not mine Structure (60-minute QBR): 1. Their business state (what's changed for them) — 15 min 2. Our partnership so far — what's working, what's not — 15 min 3. What we should do differently next quarter — 15 min 4. Commitments and next steps — 15 min Give me speaker notes and the one key question for each section.
'Built around their business, not my product' is the QBR test. If most of the slides are about me, it's a demo not a QBR.
Upsell pitch to an existing customer
PROMPT 096 / 100
Selling more to someone who already knows you — different from cold.
Pitch an expansion of [NEW PRODUCT / SCOPE] to [EXISTING CUSTOMER]. Context: - Current relationship: [DETAILS] - What they already have: [CURRENT] - What I want to add: [NEW] - Why now: [REASON] Rules for expansion pitches: - Don't re-sell. They already bought once. Assume they know me. - Lead with what's changed on THEIR side that creates the new need - Frame the new product as an extension, not a replacement - Make the commercial simple — ideally an addendum, not a new contract - Include a small risk-reducer (trial, pilot, phased rollout) Give me the 300-word proposal doc and the 60-word email introducing it.
Expansion pitches fail when they feel like the original pitch. The customer thinks: 'I already bought — why are you pitching me?' Lead with the change on their side, not the product.
Case study / testimonial request
PROMPT 097 / 100
Turn a happy customer into a marketable asset.
I want to turn [CUSTOMER] into a case study or testimonial. Context: - Their success: [OUTCOME] - Quantified results (if any): [RESULTS] - Relationship strength: [STRENGTH] - Their public vs private posture: [PUBLIC / PRIVATE / DEPENDS] Write: 1. The ask script (in-person or email) — make it easy, make it worth their time 2. The value THEY get from it (exposure, thought leadership, personal brand) 3. The specific format options (full case study, logo + quote, video testimonial, LinkedIn post, speaking slot) 4. The content review and approval process so they feel safe 5. If they say no — how to gracefully accept and keep the relationship strong Rule: don't promise marketing reach I can't deliver. Over-promising here kills trust fast.
'Make it worth their time' is the reframe. Case studies are marketing for them too, if positioned right.
Early-warning churn diagnostic
PROMPT 098 / 100
The customer's usage is dropping. What's going on?
[CUSTOMER] is showing early churn signals. Signals: [PASTE — e.g., "usage down 40% over 60 days, key user stopped logging in, ghost on last 2 QBR invites"] Diagnose: 1. The most likely root cause (rank top 3) 2. The specific question to ask that reveals the truth (not "how's it going?") 3. Who to ask — sometimes the champion knows, sometimes you need to go around them 4. The recovery play — what specifically I'd do in the next 2 weeks 5. The escalation trigger — at what point does this go from "at risk" to "all hands on deck" Be honest. If they're already gone and just haven't told us yet, that's important to know too.
The 'already gone and just haven't told us' reality check is brutal but necessary. Early acceptance enables damage control.
Customer advocate activation
PROMPT 099 / 100
Your happiest customer could be driving 3 new deals. Are they?
[CUSTOMER] is a strong advocate. I want to activate them without being extractive. Context: - Relationship: [STRENGTH] - What they've done for us already: [HISTORY] - What I'd want from them going forward: [ASK] Build an advocacy plan: 1. The tiers of advocacy — from easiest (LinkedIn like/comment) to hardest (exec intro, joint speaking slot) 2. What I'd give them in return at each tier — reciprocity is non-negotiable 3. The cadence — how often is too often (and how rare is too rare) 4. The activation script for the next-level ask 5. The "graduation" — when do I stop asking and just let them be a happy customer? Rule: advocates burn out if every interaction is an ask. Space the asks with genuine value.
Space the asks with genuine value. The best advocates are the ones who feel you give more than you take.
Multi-year expansion plan
PROMPT 100 / 100
Plot the 3-year arc, not the next-quarter tactic.
Build a 3-year expansion plan for [CUSTOMER]. Current state: - Year 1 spend: [$X] - Products / scope: [CURRENT] - Key stakeholders: [STAKEHOLDERS] - Their 3-year business direction (if known): [DIRECTION] Plan: - YEAR 2 target: product expansion, new use cases, department expansion (which is most likely?) - YEAR 3 target: strategic partnership level — exec relationships, board-level relevance, multi-product platform - For each year, the specific milestones and metrics - The risks that could derail each year - The people I need to be building relationships with NOW for the year 2-3 play Frame the plan around what THEIR business needs, not what I want to sell. If my product doesn't map to their direction, say so.
If my product doesn't map to their direction, say so. Honest reads on expansion ceiling save years of chasing.
Questions people actually ask.
Do ChatGPT prompts actually work for cold email?
Yes, if the prompt forces specificity. Generic prompts produce generic emails that get flagged and ignored. The prompts in this list force the model to reference a trigger event, a specific pain, and a single concrete ask. That's what makes them work.
Can I use these with Claude or Gemini?
Yes. Every prompt here works across Claude, Gemini, and ChatGPT with minor tuning. Claude tends to follow complex instructions more literally. Gemini is stronger on structured output. ChatGPT handles conversational tone best. For cold email, I prefer Claude. For list enrichment, Gemini.
What's the difference between these and the paid vault?
These 100 are single-purpose prompts you paste into a chat window. The paid vault is 50 full agents with memory, multi-step workflows, and ready-made connectors for Apollo, HubSpot, LinkedIn, and Gmail. Different tool for a different job.
Why free?
Because the people who'd pay $19.99 for a sales prompt pack also want to see it work before they pay. Free 100, paid 50. The paid ones are agents, not prompts.
The next step
When prompts aren't enough, agents are.
50 pre-built AI agents for B2B sales. Cold outreach, lead enrichment, LinkedIn automation, discovery prep, proposal writing. Each one runs end-to-end.
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