What's Inside
Customer success is one of the best use cases for AI — not because AI should replace human relationships, but because it should eliminate the administrative overhead that keeps CSMs from having them. The prompts below handle the prep work, the drafting, and the analysis so your team can spend their time on the conversations that actually drive retention and growth.
1Onboarding & Activation
The first 90 days determine whether a customer becomes a long-term advocate or a future churn risk. These prompts help you design onboarding experiences that are structured, personalised, and focused on getting customers to their first value milestone as fast as possible.
1.1 — Custom Onboarding Plan Generator
OnboardingPlanning
You are a customer success onboarding specialist who designs implementation plans that get customers to value fast — not just "set up."
CONTEXT:
- Customer: [COMPANY NAME, SIZE, INDUSTRY]
- Product purchased: [WHAT THEY BOUGHT AND TIER/PLAN]
- Primary use case: [WHY THEY BOUGHT — the problem they're solving]
- Key stakeholders: [WHO'S INVOLVED — champion, decision maker, end users, IT/admin]
- Success criteria: [WHAT DOES SUCCESS LOOK LIKE FOR THEM IN 90 DAYS?]
- Complexity level: [SIMPLE SELF-SERVE / GUIDED / ENTERPRISE WITH INTEGRATIONS]
- Known risks: [ANYTHING THAT COULD SLOW THINGS DOWN — competing priorities, technical debt, change resistance]
TASK:
Create a 90-day onboarding plan with:
1. Week 1: Kickoff — agenda for the kickoff call, roles and responsibilities, success milestones agreed
2. Weeks 2-4: Configuration & Setup — step-by-step technical and operational setup tasks with owners and deadlines
3. Weeks 4-8: Adoption & Training — training plan for each stakeholder group, adoption targets, and check-in cadence
4. Weeks 8-12: Optimisation & First Value — how we measure whether they've hit their success criteria, and what we adjust if they haven't
5. Risk mitigation — for each known risk, a specific prevention or response plan
6. Escalation triggers — what signals should prompt the CSM to intervene or escalate
CONSTRAINTS:
- Every task must have an owner (us or them) and a deadline — no floating to-dos
- Milestones must be outcome-based, not activity-based ("10 users active daily" not "training completed")
- The plan must be presentable to the customer — professional, clear, collaborative tone
- Include a "red flag" checklist — 5 early warning signs that onboarding is going off track
- If the customer's success criteria are vague, include a prompt to sharpen them in the kickoff
Tip: Paste in the customer's original sales notes, discovery call summary, or signed SOW alongside this prompt. The more context the AI has about what was promised during the sale, the better it can align the onboarding plan.
1.2 — Onboarding Kickoff Email
OnboardingEmail
You are a customer success manager who writes onboarding emails that make new customers feel confident, not overwhelmed.
CONTEXT:
- Customer: [COMPANY NAME]
- Main contact: [NAME AND TITLE]
- Product: [WHAT THEY PURCHASED]
- Their primary goal: [WHAT THEY WANT TO ACHIEVE]
- Kickoff call date: [DATE AND TIME]
- CSM name: [YOUR NAME]
- Anything notable from the sales process: [e.g., "they had a bad experience with a competitor," "the CEO is personally invested," "tight timeline for Q3 launch"]
TASK:
Write a welcome email that:
1. Congratulates without being cheesy — acknowledge the decision, not just the purchase
2. Sets expectations for the first 2 weeks — what will happen and in what order
3. Introduces the CSM as a person, not a role — one sentence of personality
4. Provides exactly what they need before the kickoff call (no more, no less)
5. Makes the next step crystal clear
CONSTRAINTS:
- Under 200 words — they're busy, they just signed a contract, don't make them read an essay
- No "we're so excited to have you on board!" — start with substance
- No attachments in the first email — links to resources are fine, but keep it light
- If there's something notable from the sales process, weave it in naturally to show continuity
- Subject line must feel personal, not automated (no "Welcome to [Product]! 🎉")
1.3 — User Adoption Check-In Sequence
OnboardingAdoption
You are a customer success manager who proactively drives adoption instead of waiting for users to figure things out on their own.
CONTEXT:
- Customer: [COMPANY NAME]
- Contact: [NAME — could be the champion, admin, or team lead]
- Product: [WHAT THEY'RE USING]
- Current adoption status: [e.g., "12 of 50 licences active," "using 2 of 8 features," "daily logins dropped from 30 to 8"]
- Target adoption: [WHAT GOOD LOOKS LIKE — e.g., "80% of team logging in weekly"]
- Days since go-live: [NUMBER]
- Known blockers: [IF ANY — technical issues, training gaps, competing tools]
TASK:
Write a 3-email check-in sequence designed to increase adoption:
1. Email 1 (Curious, not pushy): Acknowledge where they are, ask what's getting in the way, offer specific help — not generic "how's it going?"
2. Email 2 (Value spotlight): Share a specific use case, tip, or quick win relevant to THEIR use case that could unlock more adoption
3. Email 3 (Champion enablement): Give the champion a resource or talking point they can use to drive adoption internally — make THEM the hero
CONSTRAINTS:
- Each email under 150 words
- Never guilt-trip about low usage — focus on unlocking value, not hitting our metrics
- Each email must include a specific, actionable offer ("I can run a 15-min session for your team on X")
- Subject lines must feel like they're from a helpful human, not an automated system
- Spacing: Email 1 on day 1, Email 2 on day 5, Email 3 on day 10
1.4 — Handoff Brief (Sales → CS)
OnboardingInternal
You are a sales-to-CS handoff coordinator who ensures no context is lost when a new customer moves from the sales team to the success team.
CONTEXT:
Here are the raw notes from the sales process:
---
[PASTE: Discovery call notes, proposal, email threads, CRM notes, or any relevant sales documentation]
---
TASK:
Transform these raw notes into a structured CS handoff brief:
1. Customer snapshot — company, key contacts (with roles and communication preferences), deal size, contract terms
2. Why they bought — the real reason, not the CRM "closed reason." What pain drove the decision?
3. What was promised — any specific commitments, timelines, or expectations set during the sales process
4. Success definition — what does the customer consider a win? How will they measure it?
5. Relationship map — who's the champion, who's the decision maker, who's the skeptic, who's the end user
6. Risk flags — anything from the sales process that the CS team should know about (competing priorities, budget sensitivity, executive expectations, previous vendor failures)
7. Quick wins — what can CS deliver in the first 2 weeks to build immediate credibility?
CONSTRAINTS:
- Write for a CSM who has never spoken to this customer — they should be fully briefed after reading this
- Distinguish between what the customer explicitly said and what the sales team inferred
- "What was promised" must be specific — vague promises create churn
- Risk flags must be honest — sugarcoating helps no one
- Entire brief under 400 words — comprehensive but scannable
1.5 — Time-to-Value Accelerator
OnboardingActivation
You are a customer success strategist focused on reducing time-to-value — the period between purchase and the customer's first meaningful outcome.
CONTEXT:
- Product: [YOUR PRODUCT AND ITS CORE VALUE PROPOSITION]
- Current average time-to-value: [DAYS/WEEKS FROM PURCHASE TO FIRST VALUE MILESTONE]
- First value milestone: [WHAT IS THE CUSTOMER'S "AHA" MOMENT — the first time they get real value]
- Common delays: [WHAT TYPICALLY SLOWS CUSTOMERS DOWN — setup complexity, data migration, training gaps, internal approvals]
- Customer segments: [DO DIFFERENT SEGMENTS HAVE DIFFERENT TTV PATHS?]
TASK:
Design a time-to-value acceleration plan:
1. Current state map — walk through the typical customer journey from purchase to first value, identifying every step and its average duration
2. Bottleneck analysis — for each step, identify what causes delays and how much time each bottleneck adds
3. Acceleration opportunities — for each bottleneck, propose a specific fix (automation, pre-configuration, better docs, proactive outreach, or removal of the step entirely)
4. "Speed to value" playbook — a streamlined path that cuts TTV by at least 30%, with specific changes at each step
5. Segment-specific variations — if different segments need different paths, outline the key differences
6. Measurement framework — how to track TTV and know if the acceleration plan is working
CONSTRAINTS:
- Acceleration must not sacrifice quality — faster onboarding that creates support tickets later is not faster
- Every proposed fix must be feasible within current resources — flag anything that requires new tooling or headcount
- Include one "radical simplification" — a step that could be eliminated entirely if you challenged the assumption that it's necessary
- Measurement framework must include both leading indicators (daily) and lagging indicators (monthly)
- Be specific about expected impact — "reduce step 3 from 5 days to 1 day by pre-loading templates"
Want onboarding templates for every customer segment — SMB, mid-market, and enterprise?
The Customer Success Prompt Pack includes 60+ prompts with segment-specific versions, email sequences, and internal process templates.
Browse the CS Prompt Pack →2Health Scoring & Risk Detection
Most health scores are lagging indicators — by the time the score drops, the damage is done. These prompts help you build proactive health monitoring that catches problems early and gives your team enough runway to intervene before a customer is mentally out the door.
2.1 — Customer Health Score Framework Builder
HealthFramework
You are a CS operations architect who designs health scoring models that actually predict churn — not just report on what already happened.
CONTEXT:
- Product type: [SaaS / PLATFORM / SERVICE — describe briefly]
- Customer segments: [HOW YOU SEGMENT — by ARR, industry, tier, etc.]
- Data available: [WHAT SIGNALS YOU CAN ACTUALLY TRACK — login frequency, feature usage, support tickets, NPS, contract value, engagement with CSM, payment history]
- Current health scoring: [WHAT YOU DO NOW — or "nothing formal"]
- Known churn patterns: [WHAT DID CHURNED CUSTOMERS HAVE IN COMMON?]
TASK:
Design a customer health scoring framework:
1. Health dimensions — identify 5-7 categories of health (e.g., product adoption, relationship strength, support sentiment, business fit, contract health)
2. For each dimension: the specific metrics to track, the data source, and the scoring logic (what's green/yellow/red)
3. Weighting model — not all dimensions matter equally. Assign weights based on their predictive power for churn
4. Composite score — how to calculate an overall health score from the dimensions
5. Alert triggers — specific thresholds that should prompt CSM action, and what action to take
6. Cadence — how often to recalculate, and when to review as a team
CONSTRAINTS:
- Only include metrics you can actually measure with the stated available data — no aspirational signals
- Scoring logic must be specific: "fewer than 3 logins per week = yellow" not "low engagement = yellow"
- Weighting must be justified — explain why each dimension has its weight
- Alert triggers must include a recommended playbook action, not just "investigate"
- Include one leading indicator per dimension — something that changes before the health score does
- Acknowledge limitations — what can't this model capture, and how should CSMs compensate?
2.2 — At-Risk Account Analysis
RiskAnalysis
You are a senior CSM investigating an at-risk account to determine the root cause and build a recovery plan.
CONTEXT:
- Customer: [COMPANY NAME, ARR, SEGMENT, TENURE]
- Risk signals observed: [WHAT TRIGGERED THE ALERT — e.g., "usage dropped 40% in 30 days," "champion left," "missed last 2 QBRs," "submitted 3 escalation tickets"]
- Account history: [BRIEF TIMELINE — when they signed, any major milestones, previous issues]
- Key contacts: [WHO DO WE KNOW, AND WHAT'S THE RELATIONSHIP STATUS]
- Contract details: [RENEWAL DATE, AUTO-RENEW OR NEGOTIATED, ANY SPECIAL TERMS]
- What we've already tried: [ANY OUTREACH OR INTERVENTIONS SO FAR]
TASK:
Produce an at-risk account analysis:
1. Risk diagnosis — what is the most likely root cause? Distinguish between product issues, relationship issues, business issues, and change-of-priorities issues
2. Severity assessment — rate this as Critical / High / Moderate with rationale and estimated probability of churn
3. Stakeholder mapping — who do we need to reach, and what's the best approach for each person?
4. Recovery plan — a week-by-week action plan for the next 30 days, with specific actions, owners, and success criteria
5. Escalation recommendation — should this be escalated to leadership? If so, what do they need to know?
6. Honest assessment — is this account saveable? If so, what's the single most important thing to do this week?
CONSTRAINTS:
- Don't assume product is the problem — many at-risk accounts have a relationship or business-fit issue
- Recovery plan must include both reactive (fix the immediate issue) and proactive (rebuild the relationship) actions
- Every action must have a specific owner and timeline — no "touch base soon"
- If previous interventions failed, analyse why before suggesting more of the same
- Be honest about saveability — sometimes the right answer is to manage a graceful churn rather than fight a losing battle
2.3 — NPS / CSAT Response Templates
FeedbackResponse
You are a customer success manager who treats every NPS or CSAT response as a conversation starter — not a data point to file away.
CONTEXT:
- Customer: [COMPANY NAME, CONTACT NAME AND TITLE]
- Survey type: [NPS / CSAT]
- Score given: [NUMBER]
- Verbatim comment: [PASTE THEIR EXACT FEEDBACK]
- Account context: [ARR, TENURE, HEALTH STATUS, ANY RECENT INTERACTIONS]
TASK:
Write a personalised follow-up response for each of these three scenarios (use whichever matches the score):
PROMOTER (9-10 NPS / High CSAT):
- Thank them genuinely, reference their specific comment
- Ask for a specific favour (referral, review, case study, reference call) — pick the one most appropriate for this account
- Keep the momentum going — suggest something new they could explore
PASSIVE (7-8 NPS / Medium CSAT):
- Acknowledge the score without being defensive
- Ask one targeted question to uncover what would move them to a 9 or 10
- Offer a specific action to address their likely concern
DETRACTOR (0-6 NPS / Low CSAT):
- Lead with empathy, not damage control
- Acknowledge their specific frustration from the verbatim
- Propose a specific resolution or conversation, with a timeline
- Escalate internally if appropriate
CONSTRAINTS:
- Each response under 120 words
- Never ask "what can we do better?" — that puts the work on them. Propose something specific.
- Never challenge or reinterpret their score — accept it at face value
- Detractor responses must not include excuses or "the good news is..."
- Promoter asks must be specific and easy — "would you be open to a 15-minute reference call with a prospect in [their industry]?" not "could you spread the word?"
Pro tip: Batch your NPS responses weekly using prompt 2.3. Paste 10-15 survey responses at once, and ask the AI to generate a personalised reply for each. A CSM managing 80 accounts can close the feedback loop on every single response in under 30 minutes.
3Churn Prevention & Save Plays
By the time a customer says "we're not renewing," the decision was made weeks or months ago. These prompts help you build save plays that intervene earlier, address root causes, and give your team a structured approach to retention conversations instead of ad-hoc firefighting.
3.1 — Churn Risk Outreach (Before They Say Anything)
ChurnProactive
You are a customer success manager who reaches out to at-risk customers before they reach out to cancel — because early intervention is 3x more effective than a save call.
CONTEXT:
- Customer: [COMPANY NAME, CONTACT NAME]
- Risk signal: [WHAT YOU'VE OBSERVED — usage decline, champion left, support escalation, missed meetings, etc.]
- How long the signal has been present: [DAYS/WEEKS]
- Relationship temperature: [WARM / COOL / COLD / UNKNOWN]
- Renewal date: [DATE — how much runway do you have?]
- What you think the issue might be: [YOUR HYPOTHESIS]
TASK:
Write 2 outreach approaches:
Approach A — Direct (for warm relationships):
An email that names the signal honestly ("I noticed your team's usage has shifted") and opens a genuine conversation about whether things are working
Approach B — Indirect (for cooler relationships):
An email that offers value first — a relevant insight, resource, or success story — that gives them a reason to re-engage without feeling called out
For each approach: subject line, email body, and a suggested follow-up action if they don't respond within 5 days.
CONSTRAINTS:
- Neither email should mention churn, renewal, or cancellation — this is about value, not retention
- Direct approach must not sound accusatory — "I noticed" not "you haven't been"
- Indirect approach must deliver genuine value — if the resource isn't relevant to their use case, don't send it
- Follow-up action must escalate appropriately — don't just re-send the same email
- Each email under 130 words
3.2 — Save Call Preparation Script
ChurnSave Call
You are a customer retention specialist preparing a CSM for a save call — a high-stakes conversation where the customer has indicated they may not renew.
CONTEXT:
- Customer: [COMPANY NAME, ARR, TENURE]
- Stated reason for potential churn: [WHAT THEY TOLD US — "too expensive," "not seeing value," "switching to competitor," "budget cuts," "leadership change"]
- Account history: [KEY MILESTONES, SUCCESSES, AND PROBLEMS OVER THE RELATIONSHIP]
- What we've already tried: [PREVIOUS SAVE ATTEMPTS OR CONCESSIONS]
- What we CAN offer: [AVAILABLE LEVERS — discount, extended trial, feature access, dedicated support, executive involvement]
- What we CANNOT offer: [HARD LIMITS]
TASK:
Build a save call preparation kit:
1. Pre-call hypothesis — what's the real reason behind the stated reason? (Customers often give a surface reason that masks a deeper issue)
2. Opening approach — the first 2-3 sentences of the call, designed to listen rather than pitch
3. Discovery questions — 5 questions to understand the real situation before proposing anything
4. Value reinforcement — 3 specific results or outcomes this customer has achieved with us (pull from account history)
5. Offer strategy — if it comes to negotiation, present offers in sequence (smallest concession first)
6. Walk-away criteria — at what point should we accept the churn gracefully rather than over-concede?
7. Post-call follow-up — what to send after the call regardless of the outcome
CONSTRAINTS:
- The opening must not be defensive ("I heard you're thinking of leaving")
- Discovery questions must dig beneath the surface reason — "too expensive" might really mean "not seeing enough ROI to justify the cost"
- Value reinforcement must reference THEIR outcomes, not our features
- Offer strategy must stay within stated limits — don't promise what you can't deliver
- Walk-away criteria are essential — saving a customer at a loss is worse than a clean churn
3.3 — Win-Back Campaign (Post-Churn)
ChurnWin-Back
You are a lifecycle marketing strategist who designs win-back campaigns for churned customers — because the cheapest new customer is one you've already won once.
CONTEXT:
- Product: [YOUR PRODUCT]
- Typical churn reasons: [TOP 3-4 REASONS CUSTOMERS LEAVE]
- What's changed since they left: [NEW FEATURES, PRICING CHANGES, IMPROVEMENTS]
- Time since churn: [TARGETING CUSTOMERS WHO LEFT X MONTHS AGO]
- Segment: [ARE YOU TARGETING ALL CHURNED CUSTOMERS OR A SPECIFIC GROUP?]
TASK:
Design a 3-touch win-back sequence over 30 days:
1. Touch 1 (Day 1): The "we've changed" email — lead with what's new that directly addresses their likely churn reason. No guilt, no "we miss you."
2. Touch 2 (Day 14): The proof email — share a customer success story from a company similar to theirs who came back (or joined after similar hesitation). Include a specific metric.
3. Touch 3 (Day 28): The door-closer — a time-limited offer or incentive to return, with a clear expiration. Make the next step effortless.
For each touch: subject line, body copy, CTA, and a segmentation note (which churn reason does this touch address best).
CONSTRAINTS:
- Never say "we miss you" or "it's been a while" — leads with value, not nostalgia
- Each email under 150 words
- Touch 1 must address a real improvement, not just "we've been busy"
- Touch 3 offer must be genuine — if you don't have a real incentive, use a "VIP re-onboarding" experience instead of a discount
- Include a final opt-out line: "If [product] isn't on your radar anymore, no worries at all — I'll stop reaching out"
Building a full churn prevention playbook for your CS team?
The full pack includes save call scripts, escalation templates, executive sponsor engagement plays, and segment-specific retention strategies.
See All Prompt Packs →4QBRs & Business Reviews
The quarterly business review is the most under-leveraged touchpoint in customer success. Done poorly, it's a usage report nobody asked for. Done well, it's a strategic conversation that deepens the partnership and surfaces expansion opportunities. These prompts help you do the latter.
4.1 — QBR Deck & Talking Points Generator
QBRPreparation
You are a customer success strategist who prepares QBRs that customers actually look forward to — because they walk away with strategic value, not a usage dashboard they could pull themselves.
CONTEXT:
- Customer: [COMPANY NAME, ARR, TIER, INDUSTRY]
- Attendees: [WHO'S IN THE ROOM — titles and roles]
- Quarter in review: [Q? YYYY]
- Success metrics agreed upon: [WHAT DID WE DEFINE AS SUCCESS AT THE START OF THE ENGAGEMENT?]
- Performance data: [PASTE KEY USAGE DATA, OUTCOMES, SUPPORT TICKETS, NPS SCORES]
- Wins this quarter: [SPECIFIC OUTCOMES OR MILESTONES HIT]
- Challenges this quarter: [ISSUES, DELAYS, OR MISSES]
- Their known business priorities for next quarter: [IF KNOWN]
- Renewal date: [DATE]
TASK:
Create a QBR content package:
1. Executive summary — 3-sentence narrative of the quarter: what we set out to do, what we achieved, and what's next
2. Results section — map actual performance against success metrics. For each metric: target vs actual, trend direction, and a one-sentence interpretation
3. Value delivered — translate results into business language. Not "you had 10,000 API calls" but "your team automated 10,000 tasks that would have taken 200 hours manually"
4. Challenge acknowledgement — address issues honestly with a resolution status and forward plan for each
5. Recommendations for next quarter — 3 specific suggestions based on the data, aligned to their business priorities
6. Discussion questions — 3 strategic questions to ask the room that shift the conversation from review to planning
7. Talking points — for each section, a 2-3 sentence script the CSM can use as a guide
CONSTRAINTS:
- Frame everything through the customer's business goals, not product metrics
- The recommendations section must include at least one expansion or deepening opportunity, positioned as value — not as an upsell
- Discussion questions must be genuinely strategic — not "are you happy with the product?"
- Challenge section must be proactive, not defensive — show what you've already done to resolve issues
- Entire content package should be convertible to a 6-8 slide deck — keep it tight
4.2 — Executive Sponsor Engagement Email
QBRExecutive
You are a customer success leader who builds executive relationships — because deals renew in the boardroom, not the product.
CONTEXT:
- Customer: [COMPANY NAME]
- Executive sponsor on their side: [NAME, TITLE]
- Relationship status: [STRONG / CORDIAL / MINIMAL / NON-EXISTENT]
- Our executive sponsor: [NAME, TITLE — if assigned]
- Recent results: [1-2 HEADLINE OUTCOMES WE'VE DELIVERED]
- Upcoming event: [QBR, RENEWAL, EXPANSION CONVERSATION, OR JUST RELATIONSHIP BUILDING]
- What the executive cares about: [THEIR STRATEGIC PRIORITIES — cost reduction, growth, transformation, risk]
TASK:
Write an email to the executive sponsor that:
1. Leads with a business result they care about — in their language, not ours
2. Provides a brief forward-looking insight — something relevant to their strategic priorities
3. Makes a specific, low-friction ask — meeting, QBR attendance, or input on direction
Write two versions:
Version A — For strong/cordial relationships: warmer, more direct, assumes familiarity
Version B — For minimal/new relationships: more formal, establishes credibility before asking
CONSTRAINTS:
- Each version under 150 words — executives don't read long emails
- No product features or jargon — business language only
- The insight must be genuinely valuable — not a thinly veiled upsell
- The ask must respect their time — "15 minutes" is better than "an hour-long QBR"
- Subject line must signal executive-level content, not a CS check-in
4.3 — Post-QBR Summary & Action Plan
QBRFollow-Up
You are a customer success manager who sends QBR follow-ups that turn conversations into commitments.
CONTEXT:
Here are my notes from the QBR:
---
[PASTE YOUR RAW NOTES, TRANSCRIPT EXCERPTS, OR KEY POINTS DISCUSSED]
---
Customer: [COMPANY NAME]
Attendees: [WHO WAS THERE]
Date: [DATE]
TASK:
Transform the notes into a polished QBR follow-up email that includes:
1. A brief thank-you and one highlight from the conversation that resonated
2. Key takeaways — the 3-5 most important things discussed, written as agreed-upon statements
3. Action items table — who is doing what, by when (include both our actions and theirs)
4. Next quarter's focus — the agreed priorities and success metrics for the upcoming quarter
5. Next touchpoint — the specific date and purpose of the next scheduled interaction
CONSTRAINTS:
- Under 300 words (excluding the action items table)
- Key takeaways must be framed as mutual agreements, not our interpretation — "We agreed that..." not "I believe..."
- Action items must be specific enough that they could be dropped into a project tracker
- If something was discussed but not decided, note it as an open item requiring follow-up
- Send this within 24 hours — the email should reference the conversation while it's still fresh
Pro tip: Record your QBRs (with permission) and paste the transcript into prompt 4.3. AI is dramatically better at extracting action items and agreements from a full transcript than from your notes — and it catches things you'll forget by the time you get back to your desk.
5Renewals & Expansion
Renewal isn't a transaction — it's the culmination of every interaction over the contract period. And expansion shouldn't feel like an upsell — it should feel like the natural next step for a customer who's outgrown their current setup. These prompts help you approach both with confidence and strategic intent.
5.1 — Renewal Preparation Playbook
RenewalPlanning
You are a renewal strategist who ensures renewals are closed before the conversation starts — because the best renewal is one that was never in doubt.
CONTEXT:
- Customer: [COMPANY NAME, ARR, TIER]
- Contract end date: [DATE]
- Current health status: [GREEN / YELLOW / RED AND WHY]
- Auto-renew: [YES / NO]
- Key contacts: [CHAMPION, ECONOMIC BUYER, PROCUREMENT IF KNOWN]
- Value delivered: [TOP 3 OUTCOMES ACHIEVED DURING THE CONTRACT]
- Known risks: [BUDGET PRESSURE, CHAMPION DEPARTURE, COMPETITIVE THREAT, UNDERUTILISATION]
- Expansion opportunity: [ANY POTENTIAL UPSELL OR CROSS-SELL]
- Months until renewal: [NUMBER]
TASK:
Build a renewal playbook:
1. Renewal timeline — a reverse-engineered plan from the renewal date, showing what needs to happen at 120, 90, 60, 30, and 14 days out
2. Stakeholder strategy — who to engage, when, and with what message. Include procurement if it's an enterprise account.
3. Value story — a concise narrative of the value delivered over the contract period, written in language the economic buyer cares about
4. Risk mitigation — for each known risk, a specific pre-emptive action
5. Pricing strategy — if a price increase is planned, how to position it. If expansion is possible, how to bundle it with the renewal.
6. Negotiation preparation — what the customer is likely to ask for, and what we're prepared to offer (and what we're not)
7. Renewal email draft — the email that kicks off the formal renewal conversation
CONSTRAINTS:
- Timeline must account for procurement cycles — enterprise renewals need more lead time
- Value story must use their metrics, not ours — "you reduced X by Y%" not "you used our product Z times"
- If health status is red, the playbook must address stabilisation before renewal — don't try to renew a burning account
- Renewal email must feel like a natural extension of the relationship, not a contract notification
- Be honest about the expansion opportunity — only suggest it if the customer has signalled readiness
5.2 — Expansion Opportunity Spotter
ExpansionUpsell
You are a customer success strategist who identifies expansion opportunities that feel like natural progressions, not sales pitches.
CONTEXT:
- Customer: [COMPANY NAME, CURRENT PLAN/TIER, ARR]
- Products currently using: [LIST]
- Products NOT using (available in our portfolio): [LIST]
- Usage patterns: [KEY METRICS — power users, underused features, hitting limits]
- Their business goals: [WHAT THEY'RE TRYING TO ACHIEVE THIS YEAR]
- Expansion triggers observed: [e.g., "added 30 new users," "asking about API access," "team in new region started using it," "hitting usage caps"]
- Relationship strength: [WITH WHOM AND HOW STRONG]
TASK:
Produce an expansion opportunity assessment:
1. Opportunity identification — map each trigger to a specific expansion opportunity (new seats, higher tier, additional product, new department, new region)
2. Value case — for each opportunity, articulate how expansion directly serves their stated business goals (not why they should buy more)
3. Timing assessment — is the customer ready for this conversation now, or does readiness need to be built?
4. Approach recommendation — for each opportunity, how to introduce it: in a QBR, in a casual check-in, via the champion, or through executive engagement
5. Talk track — a 3-4 sentence conversation opener for the top opportunity that leads with their goal, not our product
6. Revenue estimate — expected ARR uplift for each opportunity
CONSTRAINTS:
- Every opportunity must connect to a customer-stated goal — if you can't make the connection, it's not the right time
- Timing assessment must be honest — pushing too early damages trust more than it gains revenue
- Talk tracks must never mention "upgrade" or "upsell" — the language should be about capability and outcomes
- If the customer isn't ready for any expansion, say so — and recommend what needs to happen first
- Prioritise opportunities by likelihood of success, not size of revenue uplift
5.3 — Multi-Year Deal Proposal
RenewalMulti-Year
You are a commercial strategist who positions multi-year deals as strategic partnerships, not just longer contracts with a discount.
CONTEXT:
- Customer: [COMPANY NAME, CURRENT ARR, TENURE]
- Current contract: [ANNUAL / ALREADY MULTI-YEAR? RENEWAL DATE]
- Proposed multi-year term: [2-YEAR / 3-YEAR]
- Discount or incentive available: [WHAT YOU CAN OFFER FOR A LONGER COMMITMENT]
- Customer's strategic direction: [WHERE THEIR BUSINESS IS HEADING OVER THE NEXT 2-3 YEARS]
- Our roadmap alignment: [HOW OUR PRODUCT DIRECTION MATCHES THEIR FUTURE NEEDS]
- Relationship strength: [EXECUTIVE BUY-IN? CHAMPION STRENGTH?]
TASK:
Build a multi-year deal proposal package:
1. Strategic positioning — frame the multi-year deal as a partnership aligned to their long-term vision, not a procurement decision
2. Value proposition — what the customer gains beyond the discount: roadmap input, dedicated resources, priority support, early access, pricing certainty
3. Deal structure — pricing breakdown showing year-over-year value, payment options, and total savings vs annual renewal
4. Growth provisions — how the contract accommodates their growth (usage tiers, seat expansion, new products) without renegotiation friction
5. Risk mitigation — address their likely concerns: "what if our needs change?" "what if the product doesn't evolve?" Include appropriate flexibility clauses
6. Proposal email — the email that presents this option to the economic buyer
CONSTRAINTS:
- The proposal must feel consultative, not transactional — "here's how we grow together" not "here's your discount for committing"
- Growth provisions must be genuinely flexible — a rigid multi-year deal creates resentment
- Risk mitigation must include a real escape mechanism — customers need to know they're not trapped
- Proposal email under 200 words — the details should be in an attached one-pager
- If the relationship isn't strong enough for a multi-year, acknowledge that and recommend what to build first
5.4 — Advocacy & Reference Program Builder
AdvocacyReferences
You are a customer marketing specialist who turns happy customers into active advocates — without making it feel transactional.
CONTEXT:
- Customer: [COMPANY NAME, CONTACT NAME AND TITLE]
- NPS score or sentiment: [SCORE OR QUALITATIVE ASSESSMENT]
- Results they've achieved: [SPECIFIC, MEASURABLE OUTCOMES]
- Relationship strength: [HOW WELL DO WE KNOW THEM? HOW LONG HAVE THEY BEEN A CUSTOMER?]
- What they've already done for us: [ANY PREVIOUS ADVOCACY — referrals, reviews, speaking engagements]
- What we need most right now: [CASE STUDY / G2 REVIEW / REFERENCE CALL / SPEAKING ENGAGEMENT / SOCIAL PROOF QUOTE]
TASK:
Create an advocacy engagement plan:
1. Ask strategy — what to ask for, when, and how to frame it so it benefits them too
2. The specific ask email — personalised to this customer, leading with gratitude and making the ask effortless
3. Preparation support — what we'll provide them (talking points, draft quotes, interview questions) so they don't have to do the work
4. Recognition plan — how we'll thank them and recognise their contribution (beyond a gift card)
5. Ongoing engagement — how to keep advocates warm for future asks without burning them out
6. Escalation path — if they say no, a graceful alternative that keeps the relationship intact
CONSTRAINTS:
- The ask must be proportional to the relationship — don't ask a 3-month customer for a keynote
- Preparation support must make saying yes nearly effortless — pre-written drafts, scheduled times, clear time commitment
- Recognition must be meaningful to THEM — not just what's easy for us to give
- Never make advocacy feel mandatory or tied to their service experience
- The ask email must be under 120 words — don't over-explain why you're asking
5.5 — Annual Customer Impact Report
ValueReport
You are a customer success storyteller who creates annual impact reports that make customers feel proud of what they've accomplished — and excited about what's next.
CONTEXT:
- Customer: [COMPANY NAME]
- Report period: [YEAR]
- Key metrics and outcomes: [PASTE ALL AVAILABLE DATA — usage stats, ROI numbers, efficiency gains, milestone achievements]
- Major milestones: [PRODUCT LAUNCHES, TEAM EXPANSIONS, PROCESS CHANGES THEY MADE WITH US]
- Challenges overcome: [PROBLEMS SOLVED DURING THE YEAR]
- Their goals for next year: [IF KNOWN]
TASK:
Create an annual impact report narrative that includes:
1. Year-in-review headline — one sentence that captures the overall story (e.g., "The year [Company] turned manual processes into automated workflows — and saved 2,400 hours doing it")
2. By-the-numbers section — 5-7 key metrics, each with a human-readable interpretation (not just the number)
3. Milestone timeline — a chronological view of the biggest moments of the year
4. Value narrative — a 2-3 paragraph story of the journey: where they started, what they built, and what changed
5. Looking ahead — how we recommend they build on this momentum next year (aligned to their goals)
6. Thank you — a genuine, personal note from the CSM
CONSTRAINTS:
- The entire report should be sendable to their executive team — professional, visual-friendly, and focused on their success (not ours)
- Numbers must be translated into business impact — "12,000 tasks automated" becomes "12,000 tasks your team didn't have to touch, equivalent to 3 full-time employees"
- The value narrative must be their story, not ours — we're the supporting character
- Looking ahead must be forward-looking and strategic, not a veiled product pitch
- Keep total narrative under 500 words — pair with a clean, designed one-pager format
This is post #4 in our weekly prompt database series.
Every week we publish a new set of copy-and-paste AI prompts for a different business function. Subscribe so you never miss a drop.
Get Weekly Prompt Drops →Why AI Works So Well for Customer Success
Customer success is uniquely suited to AI assistance — and the reason is structural. Most CS work falls into two buckets: preparation (researching accounts, building QBR decks, writing emails, analysing health data) and conversation (building relationships, navigating difficult renewals, coaching champions). AI is exceptionally good at the first bucket and useless at the second — which means it amplifies exactly where CSMs need leverage without replacing what makes them valuable.
The prompts above are designed around this split. They handle the research, drafting, and analysis so your team can spend more time in real conversations with real customers. A CSM who spends 45 minutes prepping a QBR can do it in 10 minutes with prompt 4.1 — and arrive at the meeting better prepared, with sharper talking points and more strategic questions.
The second reason these prompts work well for CS is the context layer. Customer success is inherently contextual — every account is different, every relationship has history, every renewal has nuance. Generic advice is worthless. Every prompt above requires you to load in your specific account context before the AI generates anything, which eliminates the generic problem at the source.
These prompts work across ChatGPT, Claude, Gemini, and any other major LLM. For CS work specifically, models that handle longer inputs tend to work better because you'll often want to paste in account histories, call transcripts, or usage data alongside the prompt. Choose a model that won't truncate your context.
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