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Claude plugin · 5 skills

Which accounts need you this week, and what do you do about each one?

B2B Customer Success is a free Claude plugin with five skills built on the GUARD framework: Gauge account health, Uplift expansion, Activate onboarding, Review with a QBR, and Defend the renewal. Each skill works only from the account notes you give it and marks what is missing.

What does each skill do, and who is it for?

SkillWhat it doesWho it is for
Gauge: account health
guard-gauge-diagnostic
Scores account health on six weighted signals, flags missing data and ranks a portfolio by risk.CSMs reviewing a book of business or an account that went quiet.
Uplift: expansion
guard-uplift-expansion
Checks four expansion signals and plans how to raise the expansion conversation.CSMs and account managers with a customer near its limits.
Activate: onboarding
guard-activate-onboarding
Builds a four-phase, 90-day onboarding success plan from the sales handoff.CSMs and onboarding leads with a newly signed customer.
Review: QBR and EBR
guard-review-qbr
Prepares a seven-section quarterly or executive business review brief and recap.CSMs with a business review coming up.
Defend: renewal
guard-defend-renewal
Assesses renewal risk on a 180-day countdown and builds a save plan.CSMs facing a renewal, a lost champion or a competitor evaluation.

Who is it not ideal for?

How do I install it?

Claude Code

/plugin marketplace add shashwatgtm/b2b-customer-success
/plugin install b2b-customer-success@b2b-customer-success

Or from a terminal: claude plugin marketplace add shashwatgtm/b2b-customer-success then claude plugin install b2b-customer-success@b2b-customer-success.

Cowork

  1. Open Customize in the sidebar, then Plugins.
  2. Select Add marketplace and enter shashwatgtm/b2b-customer-success.
  3. Find the plugin in the list and select Install. Its skills apply when relevant, or type / to run one.

What does it produce? Real outputs from a test run

On 25 September 2026 each skill was run once on the prompt shown, in a fresh Claude Code session with the plugin installed from GitHub. The outputs below are shown as produced, with these edits only: dashes are written out in words to match this site's style, paths to files saved on the test computer are replaced, where an output quotes this site's old byline, the author's title is updated to his current one (Co-Founder and Fractional CMO), one link a web search found to a private person's LinkedIn profile is removed (the text stays), and a placeholder attendee name that the search matched to a real person is shown as "Dana Example". Company and product names are placeholders.

Gauge: account health: real output

Prompt used in the test run (Claude Code 2.1.281, fresh session, plugin installed from GitHub; skills Claude used: b2b-customer-success:guard-gauge-diagnostic):

Here are my notes on ExampleCo: product usage is down 30% over two months, our champion moved to a different role last month, the latest NPS response was 6, renewal is in 5 months, ARR is $80k, and there are two open support tickets older than 30 days. How healthy is this account and what should I do first?

ExampleCo health check

  1. Health: about 44/100, At Risk. This is an estimate. Only 3 of the 6 health areas are backed by your data; I inferred the other 3.
  2. Main risk: the champion moved roles and usage is falling.
  3. Do first, this week (you): meet your former champion. They moved roles but still work there, so they can name who owns the tool now and introduce you. Before that meeting, get dates for fixing the two old support tickets.
  4. Escalation: tell your CS leader today. At $80k, the VP of CS isn't needed unless a competitor shows up.
  5. Deadline: renewal is about 150 days away, so the renewal risk period has already started. You need a new sponsor within 30 days, so you still have time to show value before renewal talks begin.

Score by area

AreaScoreEvidence
Product usage8/20Down 30% over two months and still falling. I don't know usage as a share of what they're paying for.
Engagement8/20Champion moved roles last month and no replacement is working with you yet (−4).
Value delivered9/20 (estimated)No ROI data. Falling usage and an NPS of 6 suggest they see only some of the value.
Customer sentiment7/15NPS of 6 (neutral-to-negative). Two tickets older than 30 days usually mean frustration is building.
Contract and payment8/15 (estimated)No payment data. Less usage probably means they're paying for more than they use.
Growth potential4/10 (estimated)Falling usage with no sign of new use cases.

Top risks

  1. No sponsor 150 days before renewal. Whoever inherited the tool didn't choose it and may not defend the budget.
  2. Usage has been dropping for 2 months. This started before the champion moved. So it's either a separate problem or an early sign they were already stepping away.
  3. Two tickets open over 30 days. This hurts your credibility with a new contact who has no reason to trust you yet.

What's working

  • The former champion still works there, so you can get a warm handoff instead of cold outreach.
  • An NPS of 6 is fixable. It isn't a detractor score.
  • Five months is enough time for a proper reset.

Actions this week

  1. Today: escalate both tickets to your support lead. Get a named owner and a fix date for each so you can give the new contact a status.
  2. Within 3 days: meet the former champion for 30 minutes. Ask who owns the tool now, why usage dropped, whether budget or priorities have changed, and whether they'll introduce you to the new owner.
  3. Within 7 days: hold a reset call with the new owner, and include an executive sponsor if you can. Don't pitch. Ask what they need the tool to do in the next 6 months, then agree on a 60-day success plan.
  4. Before the reset call: pull user-level usage to see which teams or users are driving the 30% drop.

If I'm wrong
The usage drop might come from an unfixed product problem rather than the champion moving. For example, the two old tickets could be blocking a workflow the team relies on. If so, your first priority is getting those fixed and showing it, not rebuilding the relationship. You can check this within 48 hours: see whether the drop is concentrated in the features or teams the tickets affect. If it is, fixing the tickets comes before everything else.

Missing data: usage as a share of what they pay for, NPS trend (6 down from 8 is worse than 6 up from 5), payment history, ticket severity, any mention of competitors or budget cuts.

Assumption: "moved to a different role" means the champion is still at ExampleCo. If they left the company, skip action 2 and go straight to the executive sponsor.

Next, I can build a full renewal save plan for this account, including renewal probability, a save playbook matched to the risk and talking points for the reset call.

Uplift: expansion: real output

Prompt used in the test run (Claude Code 2.1.281, fresh session, plugin installed from GitHub; skills Claude used: b2b-customer-success:guard-uplift-expansion):

ExampleCo's usage grew 40% this quarter, they are at 95% of their seat limit, and a second team (finance) asked about our reporting add-on. Current ARR is $60k and renewal is in 8 months. Is this an expansion opportunity, and how should I raise it?

Yes, this is a real expansion opportunity. It's actually two separate deals, and they should be raised at different times.

Summary

  1. Readiness: Warm, 3 of 4 signals. No risk signals in what you shared, but you didn't give a health score. Check it before you ask.
  2. Situation: The seat limit is close, and a new department wants in.
  3. Do today: Ask your champion about seats this week (you own this). Loop in your AE on the finance add-on.
  4. Hand-off: The finance reporting add-on is a cross-sell. Bring the AE in before the first finance call, not after.
  5. Deadline: Handle seats in the next 2 to 4 weeks, before they hit the limit. Close the finance add-on before or together with the renewal in 8 months.

Signals

SignalStatusEvidence
Usage✓ StrongUsage up 40% this quarter, 95% of seats in use. Anything above 90% is urgent.
Organization✓Finance asked about the reporting add-on on their own. A customer asking first is the strongest kind of signal.
Value✗ MissingThere's no documented ROI or outcome yet. You need one before you ask for money.
Timing✓Seats have to be dealt with now, mid-contract, and the renewal gives you a natural point to bundle. [Missing: finance's budget cycle]

Health check: Passes on what you gave me, since growing usage is a healthy sign. Before you pitch, confirm there are no open escalations, that your champion is still in place, and that there are no budget-cut signals. If any of those turn up, fix them first.

Two deals, two approaches

Deal A: More seats (same product, you own it)

  • Don't wait 8 months for the renewal. At 95% with 40% growth, they'll hit the limit within weeks. Once that happens, people get blocked or start sharing logins, and you end up raising it while they're annoyed.
  • Offer extra seats now, prorated so they end on the renewal date. The renewal then becomes one larger contract instead of a new negotiation.
  • Present it as keeping their team from getting stuck, not as a sale.

Deal B: Finance reporting add-on (cross-sell, you and your AE together)

  • This is a new buyer with its own budget, so find out finance's fiscal-year planning dates. That date matters more than your renewal date.
  • Suggested order: a discovery call with finance, then a scoped pilot or demo using their real reporting use case, then a proposal priced into the renewal.
  • Give your AE a hand-off brief: account health, who's who at ExampleCo, the value delivered so far, who in finance asked and what they asked, and who leads the customer conversation from here.
Rough numbers (internal only; your AE sets the actual prices)
  • Current ARR is $60k. If seat demand grows in line with usage (roughly 25 to 40% more seats), that's about $15k, $24k in extra ARR at your current per-seat rate. This is an [Assumption]: usage growth doesn't always mean the same growth in seats, so check how many active users they have and how many are waiting for access.
  • I have no pricing for the add-on, so get a quote from your AE.
  • Don't show the customer any of these numbers until your AE has approved them.
Business case outline
  • Today: [X] seats at 95% use, usage up 40% last quarter, [the one outcome they care most about: fill this in].
  • Opportunity: Enough seats for the next 2 to 3 quarters of growth, plus reporting for finance, the second department to ask.
  • Value: For finance, [time saved on reporting, or fewer manual exports]. [Missing: a reference customer who uses the reporting add-on]
  • Cost: The AE provides commercial terms.
  • Next step: A seat proposal within 2 weeks and a finance discovery call within 3 weeks.
What to say

To your champion (seats):

"Quick heads-up: you're at 95% of your seats, and usage went up about 40% last quarter. At that pace you'll hit the limit in the next few weeks. I'd like to sort that out before anyone gets locked out. We can add seats now and line them up with your renewal, so it stays one contract. Want me to send some options?"

To finance (after your champion agrees and introduces you):

"[Champion] mentioned your team asked about reporting. Before we talk about the add-on, I'd like to understand how you handle reporting today: what you pull, how often, and where it takes the most time. If it fits, we can set up a short pilot using your own data so you can see it work before anyone decides."
Close the value gap first

The weak spot is value. Before either conversation, write down one concrete result from the past quarter, like hours saved, a process sped up, or an outcome you can name. Put it in the first two sentences of the seat conversation. That's what makes asking for more money reasonable.

I can also draft the AE hand-off brief or the seat proposal email if that would help.

Activate: onboarding: real output

Prompt used in the test run (Claude Code 2.1.281, fresh session, plugin installed from GitHub; skills Claude used: b2b-customer-success:guard-activate-onboarding):

ExampleCo signed yesterday: 200 seats, mid-market manufacturing, go-live target in 60 days. Sales handoff notes: the buyer is the COO, the day-to-day owner is an operations manager, and their main goal is cutting manual reporting time by half. Build the 90-day onboarding success plan.

Executive summary

  1. Status: Day 1 of 90. Too early for a health score. Timeline is on track, but there is no baseline to measure against yet.
  2. Main risk: No baseline for reporting time.
  3. #1 action today: The CSM books a 45-minute handoff debrief with the AE (today or tomorrow) and sends a kickoff invite to the ops manager and the COO for Sept 30 or Oct 1.
  4. Escalation: None needed now. Go to the COO if the kickoff hasn't happened by Oct 1 (Day 7), or if the reporting-time baseline isn't captured by Oct 8 (Day 14).
  5. Deadline: Go-live on Day 60, Mon Nov 23, 2026. Day 90 is Wed Dec 23, which falls in holiday season, so the first business review should move earlier (see Phase 4).

Success Plan: ExampleCo

Segment: Mid-Market (200 seats, manufacturing) | ARR: [Missing] | Signed: Sep 24, 2026 (Day 0)
Cadence: Weekly check-ins until go-live, then every two weeks. Mid-market accounts normally get a check-in every two weeks, but a 60-day go-live for 200 seats needs weekly contact.

Success criteria

#OutcomeMetricTargetOwnerDue
1Cut manual reporting timeHours per week spent building reports, measured on the in-scope reportsBaseline [TBD by Day 14] → 50% lowerOps ManagerDay 90 (Dec 23)
2Production go-liveSeats provisioned and live200 of 200Ops Manager + CSMDay 60 (Nov 23)
3[To be defined at kickoff]Proposed: weekly active users as a % of seatsProposed: 70%+ by Day 90Ops ManagerDay 90

Criterion #1 can't be proven without a baseline. Nobody has measured current reporting hours yet. The Phase 1 time audit is the most important task in this plan: without it, you can't show the COO the result on Day 90.

Stakeholder map

NameRoleInfluenceEngagementNotes
[Missing]COO: economic buyer, exec sponsorDecision-makerUnknownAttends kickoff, Day 45 check-in and the business review. Wants the outcome, not the rollout details.
[Missing]Ops Manager: day-to-day owner, championDrives adoptionUnknownSingle point of failure. Manufacturing ops managers are pulled into floor issues, so protect their time.
[Missing]IT / ERP ownerBlocks or unblocks integrationsNot yet identifiedFind this person at kickoff.
[Missing]Report consumers (plant managers, finance)Validate the valueNot yet identifiedThey decide whether the new reports actually replace the old ones.
[Missing]End users (200 seats)AdoptionUnknownAre they desk staff, supervisors or shop floor? This changes the training design.

Phase 1: Foundation (Days 1 to 14, Sep 25, Oct 8)

  • ☐ Sales-to-CS handoff debrief. Confirm promises, integrations and why the target is 60 days. Owner: CSM + AE. Due Sep 25 to 26.
  • ☐ Kickoff call with the COO for the first 20 minutes, then the ops manager, IT and the CSM. Owner: CSM. Due Sep 30, Oct 1.
  • ☐ Inventory the in-scope reports: name, frequency, audience, data sources, who builds each one and how long it takes. Owner: Ops Manager. Due Oct 6.
  • ☐ Baseline time audit: 1 to 2 weeks of logged report-building hours from the people who build the reports. Owner: Ops Manager. Due Oct 8.
  • ☐ Technical plan: SSO, user provisioning, data connections (ERP/MES/spreadsheets), security review. Owner: IT + Implementation. Due Oct 8.
  • ☐ Pick a pilot group of 10 to 20 users who build or use the most time-consuming reports. Owner: Ops Manager. Due Oct 8.
  • ☐ Written success plan shared and confirmed by the ops manager, and by the COO over email. Owner: CSM. Due Oct 8.

Milestone: Baseline captured, report scope agreed, integrations scoped, pilot group named.

Phase 2: Activation (Days 15 to 30, Oct 9, Oct 24)

  • ☐ Connect data sources for the pilot reports. Owner: IT + Implementation. Due Oct 16.
  • ☐ Rebuild the top 1 to 2 most time-consuming reports in the product. Owner: Implementation + Ops Manager. Due Oct 21.
  • ☐ Pilot training on the actual report workflow, not a general product tour. Owner: CSM. Due Oct 20.
  • ☐ Train the ops manager to run training sessions themselves (train the trainer). Owner: CSM. Due Oct 23.
  • ☐ First win: one recurring report goes out through the product instead of being built by hand. Record the hours saved. Owner: Ops Manager. Due Oct 24.

Milestone: Pilot users log in every week and one manual report has been retired, with measured time saved.

Phase 3: Adoption and go-live (Days 31 to 60, Oct 25, Nov 23)

  • ☐ Rebuild the remaining in-scope reports. Owner: Implementation + Ops Manager. Due Nov 6.
  • ☐ Roll out in waves: about 60 seats by Nov 6, about 130 by Nov 13, all 200 by Nov 20. Owner: Ops Manager + CSM. Dates as shown.
  • ☐ Training sessions for each wave, plus short self-serve guides. Sessions should fit around shift schedules if needed. Owner: CSM + Ops Manager. Ongoing.
  • ☐ Day 45 check-in with the COO: pilot results against the baseline, rollout status, any help needed from the COO. Owner: CSM. Due Nov 9.
  • ☐ Go/no-go review. Owner: CSM + Ops Manager + COO. Due Nov 18.
  • ☐ Stop running the old reports alongside the new ones. If the manual versions keep going, time savings never show up. Owner: Ops Manager. Due Nov 23.

Milestone: All 200 seats live on Nov 23 and the in-scope manual reports retired.

Phase 4: Stabilize and prove value (Days 61 to 90, Nov 24, Dec 23)

  • ☐ Post-go-live office hours. Week 1 is also US Thanksgiving week, so plan for low attendance. Owner: CSM. Nov 24, Dec 4.
  • ☐ Re-run the time audit using the same method as the baseline. Owner: Ops Manager. Due Dec 11.
  • ☐ First health baseline: usage, weekly active users as a % of seats, support tickets, sentiment. Owner: CSM. Due Dec 11.
  • ☐ First business review with the COO: before-and-after reporting hours. Moved up from Day 90 because of the holidays. Owner: CSM. Due Dec 15 to 17.
  • ☐ Record next-phase use cases for later. Plant this idea without pitching it. Owner: CSM. Due Dec 17.
  • ☐ Move from the onboarding cadence to the ongoing CS cadence. Owner: CSM. Due Dec 23.

Milestone: 50% reduction shown in hours against the baseline, business review done, health baseline set.

Risk register

RiskLikelihoodImpactMitigationOwner
No baseline, so the 50% target can't be provenHighHighTime audit is a Phase 1 must-do. Escalate to the COO if it's missing on Day 14.CSM
Ops manager's bandwidth gets pulled to plant firefightingHighHighGet the COO to agree to protected hours at kickoff. Name a backup champion by Day 30.CSM + COO
ERP/MES data access or IT security review delays integrationMediumHighIdentify the IT owner at kickoff and start security review in week 1.IT + CSM
Old manual reports keep running alongside the new onesHighHighAgree on a date to retire each report, with the COO's backing.Ops Manager
"Reporting" means different things to different people, so scope creepsMediumMediumLock the report inventory by Oct 6. Anything added later goes to phase 2.CSM
Floor or shift users have little desk time for trainingMediumMediumShort, role-specific sessions and quick-reference guides.CSM
Holidays compress go-live and the business reviewMediumMediumHold the go/no-go on Nov 18 and the business review in mid-December.CSM
Single-threaded relationship (one contact)MediumHighBring in IT and report consumers by Day 30.CSM

Handoff gaps: verify with Sales before kickoff

  • [Handoff gap: ARR, tier and products/modules purchased]
  • [Handoff gap: stakeholder names and contact details]
  • [Handoff gap: anything promised on features, integrations, timeline or SLAs. Critical]
  • [Handoff gap: which reports and data sources were discussed, and whether a baseline hours number was quoted]
  • [Handoff gap: why 60 days, for example a fiscal year-end, audit or board deadline]
  • [Handoff gap: who the 200 users are and their roles]
  • [Handoff gap: competitors evaluated]

Week 1 timeline

WhenActionOwner
Fri Sep 25Handoff debrief with the AE and go through the gaps aboveCSM
Fri Sep 25Send kickoff invite, a welcome email and a 3-question prep ask (report list, data sources, IT contact)CSM
Mon Sep 28Internal prep: kickoff deck, draft of this plan, implementation resourcing confirmedCSM + Implementation
Tue Sep 29Latest date for the kickoff to be booked. Escalate if it isn't.CSM
Wed Sep 30, Thu Oct 1Kickoff call. Confirm success criteria and launch the time audit and report inventory.CSM + Ops Manager + COO
Fri Oct 2Send kickoff recap: criteria, owners, dates, next stepsCSM

Assumptions:

  • Day 0 is the signing date (Sep 24).
  • US holidays apply, so confirm the customer's region.
  • The go-live target is firm. The customer has not confirmed any specific date yet.

I can turn this into a shareable doc for ExampleCo's ops manager and COO, with internal notes like the handoff gaps and risk register left out.

Review: QBR and EBR: real output

Prompt used in the test run (Claude Code 2.1.281, fresh session, plugin installed from GitHub; skills Claude used: b2b-customer-success:guard-review-qbr):

Prepare a QBR brief for ExampleCo. Last quarter: weekly active users rose from 120 to 150 out of 200 seats, report exports doubled, and they have two open support escalations about SSO. The goals we agreed at kickoff were to cut manual reporting time by half and roll out to the finance team by Q4.

QBR Brief: ExampleCo

Summary

  1. Health: I haven't given a score because only 2 to 3 of 6 signals are available. My provisional read is Needs attention (Yellow). Adoption is strong, but support escalations are open and there's no measured value yet.
  2. Main risk: SSO problems blocking the finance rollout.
  3. Action today: CSM gets a written fix date for both SSO escalations from Support/Engineering before the QBR.
  4. Escalation: Bring in the Support lead now. If there's no fix date within 5 business days, go to the VP of CS.
  5. Deadline: Q4 starts Oct 1, 6 days from now. If "by Q4" meant the start of Q4, the finance rollout target is effectively already missed. Confirm what it meant before the meeting.

ARR: [Missing] | Renewal: [Missing] | QBR type: Standard (assumed) | Audience: [Missing: attendees; ask whether a finance lead is coming]

1. Partnership summary

Usage is growing and people are using reports more. The two kickoff goals were cutting manual reporting time by half and rolling out to finance by Q4. The reporting goal isn't being measured yet, and the finance rollout is due now. Treat this as a working session on those two goals, not a vendor update. [Missing: contract start date, stakeholder map, whether the champion has changed]

2. Value delivered
  • Reporting time (goal: cut by 50%): Not proven yet. Report exports doubled, but that shows people are using reports more, not that they save time. It could even mean more manual work, if people export to spreadsheets and build reports by hand there. Don't claim this goal is met. Offer to measure it: pick 3 to 5 recurring reports, record the hours they took before (from kickoff notes or the customer's estimate) and the hours they take now, and report the result at the next QBR.
  • Win to lead with: Weekly active users rose from 120 to 150 (+25%). That's real proof the team adopted the product, and it's their own usage data.
3. Product adoption
  • Seat usage: 150 of 200 seats are active weekly (75%, up from 60%). 50 seats are paid for but unused.
  • Hero feature: Reporting/exports. Usage doubled, and it's the feature tied to their main goal.
  • Untapped value: Find out why people export. If they rebuild reports in Excel, then scheduled or automated reports (if the product has them) are what actually cuts reporting time. [Assumption: check which features they're entitled to]
4. Support & satisfaction
  • Two open SSO escalations. Bring them up yourself and give status, owner and a fix date for each. Don't wait for them to raise it.
  • [Missing: NPS/CSAT, total ticket volume and trend, how long the escalations have been open]
5. Risk & mitigation
RiskWhy it mattersProposed action
SSO escalations block the finance rolloutFinance teams usually require SSO before going live [Assumption: confirm with the customer]Committed fix date and a named engineering owner before the QBR. Offer a joint SSO test session.
Finance rollout deadlineQ4 starts Oct 1Agree a revised date that depends on the SSO fix. Get ahead of the miss rather than letting the customer point it out.
Reporting goal unmeasuredYou can't show ROI at renewal without a measurementUse the before/after measurement plan in section 2.
25% of seats inactiveThese seats are paid for but unused, which will come up in renewal pricingFinance users can fill the idle seats (see section 6).
6. Growth opportunities

Don't pitch more seats. The best move is to fill the 50 idle seats with the finance team. That meets goal #2, gets more value from what they already pay for, and helps protect the renewal. Only raise expansion if finance plus current users go past 200 seats. [Missing: finance team headcount]

7. Forward plan

Next-quarter goals (commitments from both sides):

  • Close both SSO escalations, then launch finance on the existing seats
  • Measure reporting time on a set of recurring reports and show progress toward the 50% target
  • Get weekly active users from 150 to [target, e.g. 170+] of 200

Action items:

  • CSM: get SSO fix dates and owners from Support. Before the QBR
  • Customer IT + our Support: joint SSO validation session. Within 2 weeks of the fix
  • Customer finance lead + CSM: finance rollout plan and user list. [Date to agree in the QBR]
  • Customer ops lead: baseline hours for 3 to 5 reports. Within 2 weeks
  • CSM: reporting-time before/after results. Next QBR

To fill the [Missing] gaps before the meeting, the most useful facts are ARR, renewal date, NPS/CSAT, how long the SSO tickets have been open, and finance team size. Do you want a slide deck for the meeting or a recap email to send after it? I can also make this brief a shareable page.

Defend: renewal: real output

Prompt used in the test run (Claude Code 2.1.281, fresh session, plugin installed from GitHub; skills Claude used: b2b-customer-success:guard-defend-renewal):

ExampleCo's renewal is in 120 days, ARR is $95k, they mentioned they are evaluating a competitor, and our executive sponsor left the company last month. Usage is flat. Assess the renewal risk and give me a save strategy.

ExampleCo renewal assessment

  1. Renewal probability: about 35%, At Risk. Confidence is low because 6 of the 10 factors I'd normally score are unknown.
  2. Risk type: The sponsor left and a competitor has moved in.
  3. Your #1 action today: Find out who owns the budget now that the sponsor has gone, and ask your working-level contact for an introduction this week.
  4. Escalation: Tell your CS leader today. Because a competitor is involved, bring in your VP of CS within 48 hours and line up one of your executives to meet their new decision-maker.
  5. Deadline: Renewal is January 23, 2027. You need a relationship with the new owner by around October 10, and a formal renewal conversation by October 25 (90 days out).

Renewal date: Jan 23, 2027 | Days remaining: 120
Where you are in the cycle: Day 120 of 180. By now the sponsor should be confirmed as engaged and the business case for renewal should be underway. Neither has happened.

Risk factors (ranked by impact)

  1. Sponsor left: High. They left a month ago. A new owner usually needs 30 to 60 days to review inherited vendors, and you're already in that window. With nobody inside arguing for you, the tool becomes a line item to cut.
  2. Active competitor evaluation: High. Timing matters here. An evaluation that starts right after a sponsor leaves usually means the new owner, or someone freed up by the departure, is looking for a replacement. It isn't just background market research.
  3. Flat usage: Medium. This is actually a small positive. Users kept working through a leadership change, so the product is embedded in their workflow. But flat usage gives you no growth story to put in front of a new executive.

Positive factors

  • Usage held steady after the sponsor left, so the daily users still depend on the product.
  • 120 days is enough time for a full save. You're late but not in emergency mode.
  • Your users are your best witnesses. The switching cost for them is real.
Save strategy: sponsor departure first, then the competitor

The competitor is probably a symptom of the sponsor leaving. Rebuild the executive relationship first. If you open with competitive positioning, you'll be pitching to someone who doesn't yet know why they bought you.

Week 1 (Sep 28, Oct 2)

  • You: Map the account. Who took over the budget? Who is running the evaluation? Who are your 3 heaviest users?
  • You: Ask your strongest working-level contact for an introduction to the new owner. If the former sponsor is reachable and left on good terms, ask them to vouch for you too.
  • You and your CS leader: Write a one-page brief for the new stakeholder. Cover why they bought, what has been delivered with numbers from their own data, and what's planned next.

Week 2 (Oct 5 to 9)

  • You and one of your executives: Hold a "success reset" meeting with the new owner. Treat it as a fresh start: ask about their goals and don't mention renewal yet.
  • You: Ask directly about the evaluation. Which vendor, who started it, what problem it's meant to solve, and what the timeline is.

Weeks 3 to 4 (Oct 12 to 23)

  • You and your AE: Build a case around what switching would cost them: migration effort, retraining the users who rely on the product, lost history and integrations, and the risk of a gap in operations. Frame it around what they would lose, and don't criticise the competitor.
  • You: Get 2 or 3 power users to describe the value in their own words. A new executive trusts their own team more than they trust a vendor.
  • You: Book the formal renewal conversation for about October 26 (the 90-day mark), with a value recap and a proposed success plan for next year.

Escalation: If you still have no access to the new owner by October 16, or if they confirm a formal RFP or a pilot with the competitor, escalate to your VP of CS and ask for a meeting between their executive and yours.

Stay incentive: Keep it in reserve. Offer one only if price comes up as a real objection, and if you do, make it added value (onboarding the new executive's team, a free workshop, a price lock for multiple years) rather than a straight discount.

Conversation guide

Opener with the new owner:
"I know you've inherited a lot of vendors, and I'd rather earn your trust than assume it. Can I spend 20 minutes on what your team uses us for today and hear what you're trying to get done this year? If we don't fit that, I'd rather know now."

Raising the competitor:
"I've heard you're looking at other options, and that's reasonable with new leadership in place. What's prompting it? If there are gaps, I'd rather fix them now than find out after you've decided."

If they say "We're just doing due diligence":
"Makes sense. What criteria will you use to decide, and when? I'd like to make sure you're comparing against what your team actually uses day to day, including what a move would take."

If they say "We need to think about it":
"Of course. What specifically are you weighing, and what's your timeline? I may be able to get you information that helps."

Overdue actions
  • A baseline health check and value documentation should have been done around the end of July (day 180).
  • A relationship with the sponsor's replacement should have started within 2 weeks of their departure, which was about 2 weeks ago.
  • You should have confirmed their budget cycle. Does a January renewal fall in their fiscal year planning?
If I'm wrong

The evaluation may have nothing to do with the sponsor leaving. It could be a routine procurement exercise to get price leverage, or it could be driven by a specific missing feature that users have been complaining about. In that case the save changes:

  • If it's procurement leverage: put value documentation in front of them early and bring in your AE or Deal Desk for the commercial negotiation.
  • If it's a missing feature: confirm the gap, share a committed roadmap date or a workaround, and be honest if the gap is fundamental.

How to check within 48 hours: Ask your working-level contact, "When did the evaluation start, and who asked for it?" If it began before the sponsor left, or procurement is running it, you're in one of these other situations.


Missing: NPS or sentiment, open escalations, payment history, how much of their contracted entitlement they use, how many contacts you have there, and which competitor it is. The probability above is estimated from 4 signals and could move 15 points either way once you have these. If you share the competitor's name, I can build a battle card for this deal.

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