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●  First look for the CEO
$7.47M

of revenue is stuck, at risk or leaking at Northwind Cloud. 24 findings, each with a dollar value, an owner and the records behind it.

$22.99MARR
278Paying customers
$7.07MOpen pipeline
5 systemsCRM · billing · support · usage · Slack
01  Where the money sits

Sold → live → used → billed → collected → renewed

Every dollar moves along one chain. Stuck money is money sitting too long at one step.

01 · Sold
$3.10M
Pipeline that stopped moving, and price given away to close.
6 findings
02 · Live
$152k
Signed and paying, but nobody is using it yet.
2 findings
03 · Billed
$77k
Used more than paid for. Earned, never invoiced.
2 findings
04 · Collected
$694k
Invoiced, but the cash has not come in.
7 findings
05 · Renewed
$3.45M
Renewals at risk, and revenue already shrinking.
7 findings
02  The 10 biggest stuck items

Ranked by dollars.

Each one joins facts no single person sees: the CRM says one thing, usage, billing, tickets and Slack say another.

01

Caleb Fenn: 8 of 8 open deals stuck in Legal

$1.18M
Stuck pipelineOwner: Caleb Fenn

Every one has sat in Legal 33-58 days; team median for Legal is 9 days.

#deals-desk · 2026-11-06 · Petra Voss“8 of Caleb's deals are sitting in legal, oldest 58 days. what is blocking?”
Proof · 8 records
  • deal D0916 Duskmoor Clinics $116k, in Legal since 2026-09-15
  • deal D0915 Zephyrine Robotics $103k, in Legal since 2026-09-21
  • deal D0914 Driftwood Finance $123k, in Legal since 2026-09-27
  • deal D0917 Willowmere Analytics $123k, in Legal since 2026-09-29
  • deal D0913 Fernhollow Clinics $228k, in Legal since 2026-10-02
  • deal D0912 Duskmoor Labs $127k, in Legal since 2026-10-05
  • deal D0918 Umberfield Studios $196k, in Legal since 2026-10-07
  • deal D0911 Umberfield Health $166k, in Legal since 2026-10-10

Next step Sales lead to review legal terms with Caleb Fenn; offer standard paper.

02

Cohort 2025-Q2: 7 of 22 customers churned

$870k
Revenue retention

Churn rate 32% vs. median 7% across cohorts. Most left at first renewal.

#cs-team · 2026-06-15 · Noor Haddad“another customer from the spring 2025 batch gone. that batch never finished onboarding.”
Proof · 7 records
  • Tidewater Health (S0011) canceled 2026-06-08, ARR $515k
  • Umberfield Finance (S0022) canceled 2026-04-06, ARR $231k
  • Harborlight Supply (S0061) canceled 2026-04-23, ARR $38k
  • Larkspur Health (S0095) canceled 2026-06-24, ARR $55k
  • Moonrise Studios (S0203) canceled 2026-05-06, ARR $11k
  • Duskmoor Foods (S0234) canceled 2026-04-23, ARR $5k
  • Pinecrest Health (S0289) canceled 2026-05-29, ARR $14k

Next step Review what that quarter's onboarding missed; check the same signs in today's new customers.

03

Foxbriar Foods: no exec contact in 164 days, renews in 64 days

$588k
At-risk revenueFoxbriar FoodsOwner: Sofia Lind

Last exec meeting 2026-06-01. 0 open tickets. CRM health 'Green'.

#cust-foxbriar-foods · 2026-11-03 · Soren Quarles (customer)“third outage this month, escalating to our CIO”
Proof · 2 records
  • last exec activity 2026-06-01
  • subscription S0027 renews 2027-01-15, ARR $588k

Next step Our exec calls their exec this week.

04

Dev Marlow: 12 deals closed at 30%+ off

$583k
Price leakOwner: Dev Marlow

Average discount 40% on these deals vs. team average 14%. Given away every year these customers renew.

#deals-desk · 2026-09-13 · Petra Voss“approved 40% again on Larkspur Robotics for Dev. we need the logo.”
Proof · 12 records
  • deal D0389 Tidewater Freight: list $6k, sold $4k (44% off), 2026-09-16
  • deal D0338 Saltmarsh Supply: list $15k, sold $9k (43% off), 2026-05-05
  • deal D0585 Larkspur Robotics: list $6k, sold $3k (42% off), 2026-05-05
  • deal D0306 Tidewater Robotics: list $9k, sold $5k (41% off), 2026-01-30
  • deal D0390 Tidewater Supply: list $13k, sold $8k (40% off), 2026-07-18
  • deal D0112 Larkspur Energy: list $147k, sold $88k (40% off), 2026-07-09
  • deal D0022 Umberfield Labs: list $858k, sold $521k (39% off), 2026-05-13
  • deal D0101 Oakmere Finance: list $147k, sold $90k (39% off), 2026-02-09
  • deal D0521 Yellowfin Labs: list $10k, sold $6k (38% off), 2026-07-18
  • deal D0091 Fernhollow Finance: list $136k, sold $85k (38% off), 2026-08-17
  • deal D0444 Ashgrove Health: list $10k, sold $6k (36% off), 2026-08-13
  • deal D0149 Granitebay Media: list $140k, sold $90k (36% off), 2026-01-26

Next step Sales lead approves anything over 20%; reset price at renewal.

05

Brackenfold Studios: usage down 52%, renews in 58 days

$545k
At-risk revenueBrackenfold StudiosOwner: Sofia Lind

Weekly active users 465 -> 224. CRM health says 'Green'. 2 open tickets.

Proof · 3 records
  • usage, last 12 weeks: [486, 451, 478, 462, 450, 464, 407, 384, 321, 287, 213, 173]
  • subscription S0030 renews 2027-01-09, ARR $545k
  • CRM health field: Green

Next step CSM call this week: find who stopped using it and why.

06

Copperleaf Foods: cut 798 seats at renewal

$517k
Revenue retentionCopperleaf FoodsOwner: Sofia Lind

Seats 1463 -> 665 on 2026-08-29 (55% cut).

#cs-team · 2026-08-30 · Sofia Lind“Copperleaf Foods cut seats at renewal, they said 'only one team really uses it'.”
Proof · 2 records
  • subscription S0009 change on 2026-08-29
  • ARR now $430k

Next step Find the teams that stopped using it; win-back plan before the next renewal.

07

One problem, 6 accounts: 'export-timeout' (14 tickets in 45 days)

$490k
At-risk revenue

New issue: 14 tickets from 6 accounts in 45 days, none before. 6 of them renew within 90 days.

#support-escalations · 2026-10-31 · Jonah Pike“Ironbark Systems says they won't renew without the export fix. 4th account this month on export timeouts.”
Proof · 7 records
  • tickets: T03233, T03234, T03235, T03236, T03237, T03238, T03239, T03240, T03241, T03242, T03243, T03244, T03245, T03246
  • Ironbark Systems renews 2026-12-06
  • Willowmere Robotics renews 2026-12-19
  • Foxbriar Retail renews 2026-12-27
  • Quarrystone Media renews 2027-01-10
  • Elmstead Health renews 2027-01-17
  • Fernhollow Studios renews 2027-02-03

Next step Get engineering a fix date; CSMs tell each account before renewal.

08

Saltmarsh Robotics: Negotiation for 64 days

$418k
Stuck pipelineSaltmarsh RoboticsOwner: Mara Quill

64 days in Negotiation (team median 12). Last activity 30 days ago.

#deal-saltmarsh-robotics · 2026-10-20 · Mara Quill“Saltmarsh Robotics: they went quiet after the pricing call. third follow-up, no reply.”
Proof · 4 records
  • deal D0907 (new), $418k
  • stage history: Negotiation since 2026-09-09
  • last logged activity 2026-10-13
  • close date 2026-12-16, moved 0x

Next step Exec-to-exec call this week, or mark lost.

09

Brackenfold Health: Negotiation for 53 days

$352k
Stuck pipelineBrackenfold HealthOwner: Ines Varga

53 days in Negotiation (team median 12). Last activity 33 days ago.

#deal-brackenfold-health · 2026-10-12 · Ines Varga“Brackenfold Health procurement wants 20% off before they sign. parked until they come back.”
Proof · 4 records
  • deal D0908 (new), $352k
  • stage history: Negotiation since 2026-09-20
  • last logged activity 2026-10-10
  • close date 2026-12-01, moved 0x

Next step Exec-to-exec call this week, or mark lost.

10

Willowmere Clinics: $350k late, 185 days

$350k
Billed, not collectedWillowmere ClinicsOwner: Ines Varga

2 invoice(s) past due. Last contact of any kind: 2026-08-09 (95 days ago). CRM health 'Green'.

Proof · 3 records
  • invoice INV-10056 $175k, due 2026-05-11, 185 days late
  • invoice INV-10057 $175k, due 2026-08-10, 94 days late
  • last activity 2026-08-09

Next step Finance calls their AP today; AE emails their sponsor.

03  By offer

Start with one.

The three offers sellers lead with. Same brain, different slice.

$2.51M

of $7.07M open pipeline (36%) is stuck: parked past twice the normal time in its stage, or slipping.

Offer: Pipeline clean-up · data: CRM only · from $1k-2k a month
● Data health

Data health: 7 open deals have no next step, 11 have a close date in the past

7% of 94 open deals have no next step. 11 close dates are already behind us. $720k of pipeline is affected.

Proof · deal ids
  • no next step: D0827, D0828, D0834, D0837, D0861, D0892, D0902
  • close date in past: D0817, D0823, D0824, D0829, D0833, D0851, D0858, D0868, D0874, D0876, D0889

Next step Reps fix next steps and dates before Friday's forecast call.

Caleb Fenn: 8 of 8 open deals stuck in Legal

$1.18M
Stuck pipelineOwner: Caleb Fenn

Every one has sat in Legal 33-58 days; team median for Legal is 9 days.

#deals-desk · 2026-11-06 · Petra Voss“8 of Caleb's deals are sitting in legal, oldest 58 days. what is blocking?”
Proof · 8 records
  • deal D0916 Duskmoor Clinics $116k, in Legal since 2026-09-15
  • deal D0915 Zephyrine Robotics $103k, in Legal since 2026-09-21
  • deal D0914 Driftwood Finance $123k, in Legal since 2026-09-27
  • deal D0917 Willowmere Analytics $123k, in Legal since 2026-09-29
  • deal D0913 Fernhollow Clinics $228k, in Legal since 2026-10-02
  • deal D0912 Duskmoor Labs $127k, in Legal since 2026-10-05
  • deal D0918 Umberfield Studios $196k, in Legal since 2026-10-07
  • deal D0911 Umberfield Health $166k, in Legal since 2026-10-10

Next step Sales lead to review legal terms with Caleb Fenn; offer standard paper.

Saltmarsh Robotics: Negotiation for 64 days

$418k
Stuck pipelineSaltmarsh RoboticsOwner: Mara Quill

64 days in Negotiation (team median 12). Last activity 30 days ago.

#deal-saltmarsh-robotics · 2026-10-20 · Mara Quill“Saltmarsh Robotics: they went quiet after the pricing call. third follow-up, no reply.”
Proof · 4 records
  • deal D0907 (new), $418k
  • stage history: Negotiation since 2026-09-09
  • last logged activity 2026-10-13
  • close date 2026-12-16, moved 0x

Next step Exec-to-exec call this week, or mark lost.

Brackenfold Health: Negotiation for 53 days

$352k
Stuck pipelineBrackenfold HealthOwner: Ines Varga

53 days in Negotiation (team median 12). Last activity 33 days ago.

#deal-brackenfold-health · 2026-10-12 · Ines Varga“Brackenfold Health procurement wants 20% off before they sign. parked until they come back.”
Proof · 4 records
  • deal D0908 (new), $352k
  • stage history: Negotiation since 2026-09-20
  • last logged activity 2026-10-10
  • close date 2026-12-01, moved 0x

Next step Exec-to-exec call this week, or mark lost.

Tidewater Analytics: Negotiation for 47 days

$296k
Stuck pipelineTidewater AnalyticsOwner: Ines Varga

47 days in Negotiation (team median 12). Last activity 44 days ago.

#deal-tidewater-analytics · 2026-10-03 · Ines Varga“Tidewater Analytics: our champion there is on leave, nobody else engaged. deal is stalled.”
Proof · 4 records
  • deal D0909 (new), $296k
  • stage history: Negotiation since 2026-09-26
  • last logged activity 2026-09-29
  • close date 2026-11-26, moved 0x

Next step Exec-to-exec call this week, or mark lost.

Foxbriar Labs: close date pushed 4 times

$264k
Stuck pipelineFoxbriar LabsOwner: Ines Varga

Close date moved 4 times since 2026-07-25; still in Proposal.

#deal-foxbriar-labs · 2026-11-03 · Ines Varga“Foxbriar Labs pushed the date again, now 'after their budget meeting'”
Proof · 5 records
  • deal D0910, $264k
  • moved 2026-08-09 -> 2026-09-03 on 2026-07-25
  • moved 2026-09-03 -> 2026-09-28 on 2026-08-19
  • moved 2026-09-28 -> 2026-10-23 on 2026-09-13
  • moved 2026-10-23 -> 2026-12-03 on 2026-10-08

Next step Ask the buyer for a mutual close plan with dates, or take it out of the forecast.

$694k

billed and not collected: invoices 30+ days late, and card payments that keep failing.

Offer: Cash chaser · data: billing + CRM · from $2k-4k a month
All open invoices by age
Not due$1.61M
1-30 late$556k
31-60 late$120k
61-90 late$0
90+ late$550k

Willowmere Clinics: $350k late, 185 days

$350k
Billed, not collectedWillowmere ClinicsOwner: Ines Varga

2 invoice(s) past due. Last contact of any kind: 2026-08-09 (95 days ago). CRM health 'Green'.

Proof · 3 records
  • invoice INV-10056 $175k, due 2026-05-11, 185 days late
  • invoice INV-10057 $175k, due 2026-08-10, 94 days late
  • last activity 2026-08-09

Next step Finance calls their AP today; AE emails their sponsor.

Driftwood Media: $200k late, 133 days

$200k
Billed, not collectedDriftwood MediaOwner: Theo Brandt

1 invoice(s) past due. Last contact of any kind: 2026-08-30 (74 days ago). CRM health 'Green'.

#finance · 2026-10-23 · Omar Reyes“anyone own Driftwood Media? invoice INV-10069 still open. AE says it's CS, CS says it's sales.”
Proof · 2 records
  • invoice INV-10069 $200k, due 2026-07-02, 133 days late
  • last activity 2026-08-30

Next step Finance calls their AP today; AE emails their sponsor.

Driftwood Robotics: $37k late, 50 days

$37k
Billed, not collectedDriftwood RoboticsOwner: Rafi Osei

1 invoice(s) past due. Last contact of any kind: 2026-10-31 (12 days ago). CRM health 'Green'.

Proof · 2 records
  • invoice INV-10126 $37k, due 2026-09-23, 50 days late
  • last activity 2026-10-31

Next step Finance calls their AP today; AE emails their sponsor.

Failed card payments: 30 accounts, $25k MRR

$35k
Billed, not collected

43 open invoices with failed charges and no success; first failure 2026-09-25. Dunning has not recovered any of them.

#finance · 2026-10-18 · Omar Reyes“card retries failing for a bunch of small accounts since early October. are dunning emails even going out?”
Proof · 43 records
  • Driftwood Systems invoice INV-10459 $1k, 4 failed tries
  • Driftwood Systems invoice INV-10460 $1k, 1 failed tries
  • Emberline Clinics invoice INV-10503 $1k, 4 failed tries
  • Ashgrove Retail invoice INV-10762 $659, 4 failed tries
  • Tidewater Clinics invoice INV-10847 $812, 4 failed tries
  • Ironbark Studios invoice INV-10859 $998, 4 failed tries
  • Emberline Energy invoice INV-10895 $965, 4 failed tries
  • Moonrise Clinics invoice INV-10961 $696, 4 failed tries
  • Moonrise Clinics invoice INV-10962 $696, 2 failed tries
  • Elmstead Foods invoice INV-10973 $866, 4 failed tries
  • Elmstead Foods invoice INV-10974 $866, 2 failed tries
  • Quarrystone Retail invoice INV-11033 $615, 4 failed tries
  • Quarrystone Retail invoice INV-11034 $615, 4 failed tries
  • Moonrise Energy invoice INV-11118 $432, 4 failed tries
  • + 29 more records

Next step Email + call each to update the card; offer ACH for the bigger ones.

Pinecrest Retail: $28k late, 48 days

$28k
Billed, not collectedPinecrest RetailOwner: Theo Brandt

1 invoice(s) past due. Last contact of any kind: 2026-11-06 (6 days ago). CRM health 'Green'.

Proof · 2 records
  • invoice INV-10114 $28k, due 2026-09-25, 48 days late
  • last activity 2026-11-06

Next step Finance calls their AP today; AE emails their sponsor.

Pinecrest Energy: $27k late, 47 days

$27k
Billed, not collectedPinecrest EnergyOwner: Mara Quill

1 invoice(s) past due. Last contact of any kind: 2026-10-24 (19 days ago). CRM health 'Green'.

Proof · 2 records
  • invoice INV-10118 $27k, due 2026-09-26, 47 days late
  • last activity 2026-10-24

Next step Finance calls their AP today; AE emails their sponsor.

Saltmarsh Foods: $17k late, 54 days

$17k
Billed, not collectedSaltmarsh FoodsOwner: Theo Brandt

1 invoice(s) past due. Last contact of any kind: 2026-10-19 (24 days ago). CRM health 'Green'.

Proof · 2 records
  • invoice INV-10122 $17k, due 2026-09-19, 54 days late
  • last activity 2026-10-19

Next step Finance calls their AP today; AE emails their sponsor.

$490k

of ARR sits with customers hit by the same new problem, most of them renewing soon.

Offer: Repeat-problem finder · data: support + billing · from $2k-4k a month

One problem, 6 accounts: 'export-timeout' (14 tickets in 45 days)

$490k
At-risk revenue

New issue: 14 tickets from 6 accounts in 45 days, none before. 6 of them renew within 90 days.

#support-escalations · 2026-10-31 · Jonah Pike“Ironbark Systems says they won't renew without the export fix. 4th account this month on export timeouts.”
Proof · 7 records
  • tickets: T03233, T03234, T03235, T03236, T03237, T03238, T03239, T03240, T03241, T03242, T03243, T03244, T03245, T03246
  • Ironbark Systems renews 2026-12-06
  • Willowmere Robotics renews 2026-12-19
  • Foxbriar Retail renews 2026-12-27
  • Quarrystone Media renews 2027-01-10
  • Elmstead Health renews 2027-01-17
  • Fernhollow Studios renews 2027-02-03

Next step Get engineering a fix date; CSMs tell each account before renewal.

Ticket topic (last 45 days)TicketsUsualAccountsARR touched
report-error643852$7.54M
permissions633944$7.83M
sso573846$8.83M
login573949$8.82M
how-to534340$6.62M
billing-question533844$8.84M
integration524044$7.87M
data-import523646$7.98M
slow-dashboard504042$9.13M
api-limits454437$5.96M
export-timeout new spike1406$490k
7

core metrics the brain watches for every client. Same code for every company; only the mapping changes.

01

Stuck pipeline

before sold$2.51M
  • Caleb Fenn: 8 of 8 open deals stuck in Legal$1.18M
  • Saltmarsh Robotics: Negotiation for 64 days$418k
  • Brackenfold Health: Negotiation for 53 days$352k
  • Tidewater Analytics: Negotiation for 47 days$296k
  • Foxbriar Labs: close date pushed 4 times$264k
02

Signed, not live

sold → live$152k
  • Cindervale Systems: signed 97 days ago, not live$85k
  • Glimmerton Media: signed 62 days ago, not live$67k
03

Revenue retention

→ renewed$1.39M
  • Cohort 2025-Q2: 7 of 22 customers churned$870k
  • Copperleaf Foods: cut 798 seats at renewal$517k
04

At-risk revenue

→ renewed$2.06M
  • Foxbriar Foods: no exec contact in 164 days, renews in 64 days$588k
  • Brackenfold Studios: usage down 52%, renews in 58 days$545k
  • One problem, 6 accounts: 'export-timeout' (14 tickets in 45 days)$490k
  • Cindervale Analytics: usage down 48%, renews in 96 days$308k
  • Elmstead Labs: champion left, renews in 71 days$129k
05

Earned, not billed

used → billed$77k
  • Yellowfin Foods: 92 users over plan, not billed$48k
  • Willowmere Media: 63 users over plan, not billed$29k
06

Billed, not collected

billed → collected$694k
  • Willowmere Clinics: $350k late, 185 days$350k
  • Driftwood Media: $200k late, 133 days$200k
  • Driftwood Robotics: $37k late, 50 days$37k
  • Failed card payments: 30 accounts, $25k MRR$35k
  • Pinecrest Retail: $28k late, 48 days$28k
  • Pinecrest Energy: $27k late, 47 days$27k
  • Saltmarsh Foods: $17k late, 54 days$17k
07

Price leak

at sold$583k
  • Dev Marlow: 12 deals closed at 30%+ off$583k