Lost & Delayed Deals

Q4 2025 + Q1 2026 (Oct 2025 – Mar 2026) | Source: HubSpot CRM + Grain AI Call Intelligence

$8.36M in pipeline across 34 strategic deals closed lost or delayed in Q4 2025 + Q1 2026. A significant majority (estimated 60–85%) traces to addressable root causes — execution gaps, positioning mismatches, and process failures. Only $1.35M (4 deals) was lost to genuinely external events: acquisitions by Stripe, Google, and IBM, plus one project cancellation. Why we lose: The leading controllable driver is prospects going dark mid-cycle ($1.46M, 5 deals) — in every case, the team failed to establish a critical event or secure an executive sponsor. MEDDIC-first requirements ($720K lost + $500K delayed) and named competitors ($1.20M, 4 deals) follow. What customers ask for: Grain call analysis across 40+ recordings reveals the #1 prospect concern is "will this stick?" — methodology operationalized in tools, not delivered as training events. MEDDIC coexistence is the universal tension. ICP targeting: Only ~44% of lost pipeline was within our defined $50M–$2B ICP (based on HubSpot enrichment estimates, not verified ARR). ~24% was above ICP (enterprise logos where we're outscaled) and ~12% was below ICP. $1.0M remains recoverable across 3 delayed deals with active paths.
$8.36M
Total Value
34
Strategic Deals
$246K
Avg Deal
28
Closed Lost
3
Delayed
$1.0M
Recoverable
3
Data Quality

Why We Lose

Each deal classified by primary loss driver. HubSpot closed_lost_reason + Grain call analysis used for classification.

Pipeline Value by Loss Reason
Deal Count by Loss Reason
Loss Reasons — Ranked by Value
Went Dark
$1.46M
5 deals
External Event
$1.35M
4 deals
MEDDIC-First
$1.22M
5 deals
Competitor
$1.20M
4 deals
No Priority
$925K
5 deals
Rescoping
$650K
3 deals
Price
$437K
2 deals
Champion Left
$460K
3 deals
DIY / In-House
$295K
1 deal
Access / Fit
$240K
2 deals

Controllable vs. uncontrollable: $1.35M (4 deals) was lost to events outside WbD's influence — Metronome acquired by Stripe ($386K), Wiz UK frozen by Google acquisition ($166K), Teknor Apex cancelled internally ($150K), and Confluent acquired by IBM ($100K). The remaining $7.01M spans execution gaps, positioning mismatches, and competitive losses. Some borderline cases (e.g., "went dark" could reflect either weak execution or genuine buyer-side chaos) mean the controllable share likely falls in a 60–85% range. Regardless of the exact figure, the direction is clear: most of this pipeline was addressable.

Methodology note: Loss reasons classified using HubSpot closed_lost_reason field + Grain call analysis. ICP segmentation uses HubSpot enrichment-estimated annual revenue, which may differ from verified ARR. Recommend spot-checking 5 deals for classification accuracy.

ICP Fit Analysis — $50M–$2B ARR

Company annual revenue from HubSpot enrichment mapped against defined ICP of $50M–$2B ARR. Note: HubSpot revenue estimates may differ from verified ARR — some values appear inflated (e.g., WP Engine at $10B vs. ~$400M actual). Treat as directional, not precise.

Pipeline by ICP Segment
ICP Breakdown
In ICP ($50M-$2B)
$3.70M — 17 deals
44%
Above ICP (>$2B)
$2.04M — 10 deals
24%
Below ICP (<$50M)
$991K — 4 deals
12%
Unknown / No Data
$1.03M — 4 deals
12%

Above-ICP pattern: 10 deals worth $2.04M targeted companies above $2B (Okta, Siemens, Rakuten, DXC, Digital Realty, Check Point, TD SYNNEX). These are enterprise logos where procurement complexity, MEDDIC requirements, and incumbent vendor relationships create structural disadvantages. 4 of the 5 MEDDIC-first losses came from above-ICP companies.

Below-ICP pattern: Lambda Labs ($1M ARR) accounted for $505K across 2 deals. Cerby ($10M) lost $100K. Below-ICP companies may lack the RevOps infrastructure to operationalize methodology at scale — creating both delivery risk and a "stickiness" gap.

ICP targeting implication: If the team had focused exclusively on in-ICP deals, the loss pool shrinks from $8.36M to $3.70M. The remaining $4.66M in out-of-ICP losses represents either deliberate strategic bets (requiring different playbooks) or undisciplined pipeline that inflates reporting without improving win rates.

Competitive Landscape

Named competitors appearing in lost deal reasons. Deals where a specific competitor was cited as the winner.

Sandler
3 deals — $700K
Contentful ($400K) — CRO had longstanding Sandler relationship; shaped the brief. WbD was runner-up of 8 vendors.
FrontApp ($150K) — No enablement person for 2 years; Sandler won on familiarity.
NBCUniversal ($300K)* — Some leaders had prior Sandler success; included org diagnostic.
Pattern: Sandler wins on incumbent relationships, not capability
MEDDIC Vendors
5 deals — $1.22M
JFrog ($400K) — Preferred MEDDIC more central to training.
Maxar ($250K) — "MEDDIC is requirement" — CTO/CEO demanded it.
Okta ($250K) — MEDDIC alignment was the stated need.
Rakuten ($120K) — CEO wanted MEDDIC as a "quick win."
Cerby ($100K) — 1mind took the deal solo as a MEDDIC shop; WbD design element wasn't enough.
Pattern: Prospects want MEDDIC AND methodology — not either/or
Value Selling
1 deal — $500K
First Advantage ($500K) — Incumbent from acquired Sterling had existing relationship with 551 GTM reps.
Pattern: Acquisition-inherited vendor relationships hard to displace
DIY / In-House
1 deal — $295K
Check Point ($295K) — Decided to build SKO content in-house rather than engage external vendor.
Signal: Larger orgs increasingly building internal enablement capability

* NBCUniversal closed Sep 29, 2025 — included for competitive pattern completeness. All other deals within Q4 2025 + Q1 2026.

What Customers Actually Ask For

Patterns from Grain call recordings — what prospects say in their own words during discovery and evaluation.

1. Sales Methodology (Not Just Training)

Prospects consistently distinguish between methodology and training events. They want a system that changes how their team operates daily.

"I want a sales methodology. I have a lot of background — I actually contributed to the Challenger Sale. I don't consider Challenger to be a sales methodology. It's a choreography. People say MEDDIC is a methodology — it's a deal qualification. I want to guide my people through the sales process based on a proven, sound methodology." — Bryan Miller, ASCM | Discovery call with Betsy Peters, Feb 18 2026
"That was my $50,000 way to do what we spent $750,000 at Calendly to do with Winning by Design. What we did at Calendly didn't stick. We had to keep coming back. It was a training event. We built our Salesforce environment to model the bowtie workflow, exit entrance criteria. But people didn't do SPICED on a call — that never stopped." — Amy McClain, Affirm | Discovery call with Matt Kaminski, Mar 31 2026

2. MEDDIC Coexistence (Not Replacement)

Prospects with existing MEDDIC implementations want SPICED to complement their qualification framework, not compete with it.

"We have regional managers requesting a methodology. I don't think they necessarily know why, but they see MEDDIC in Salesforce and are connecting the dots. Adoption is super low — and that's why it failed in the past." — Leanne Sutherland, Akamai | Discovery call with Betsy Peters, Feb 18 2026
"They've got methodology fatigue where they tried Challenger for a year, replaced it with MEDDIC. I don't think any of it was operationalized. I say the word methodology and they all just get the shakes." — Amy McClain, Affirm | Discovery call with Matt Kaminski, Mar 31 2026

3. Operationalization — "Making It Stick"

The #1 concern across conversations: will this actually change behavior, or will it be another training event?

"Is there any guidance on making sure this sticks? We've taken our Salesforce statuses and tied them to the methodology. But is there anything beyond signing up for multiple sessions?" — Jim Grass, Singlewire | Follow-up with Betsy Peters, Mar 3 2026
"We've changed our sales process — new stages, new percentages, and within that we also introduced SPICED exit criteria. Stage three, one of the exit criteria is you got to engage professional services. We feel like we can certainly do better and mature." — Marco Cantamessi, IR (existing customer) | Advisory with David Ellin, Mar 4 2026

4. Cross-Functional Operating System (Beyond Sales)

Advanced prospects see SPICED as a company-wide operating language, not just a sales tool.

"We're using SPICED for onboarding where we're going to leverage SPICED methodology embedded in Salesforce by the AE to auto-populate in Gainsight so that our CSM and AM team are actually using that when doing a handoff." — Helen, Level Access (existing customer) | Advisory with David Ellin, Feb 11 2026

5. The Buyer Psychology Shift — Fear of Messing Up

Across WbD's own customers' pipelines, Grain reveals a macro shift in buyer behavior that directly mirrors our own loss patterns.

"The majority of the deals we lose, we lose because people go dark. To me, that means there was no critical event discovered." — Julie Engel, TrackStreet (WbD customer) | Impact review, Mar 2 2026
"We used to deal with fear of missing out and now it's more fear of messing up and indecision." — Rachael Smith, WbD | TrackStreet advisory, Mar 2 2026
"Indecision and doing nothing or ghosting is probably our highest [loss reason]. Direct to competitors, probably 15-20%." — Josh Tenby, Thinkific | Discovery call, Mar 10 2026

The indecision pattern is self-referential. Our customers' #1 loss reason (status quo / went dark) is also our #1 loss reason ($1.46M). The root cause is the same: insufficient discovery depth, no critical event established, and no quantified impact to justify action. CData's Claude-built dashboard shows that when Impact and Decision fields in SPICED are empty, loss rates spike. This is both a product insight and a sales execution gap.

Strategic Insights for ELT

The MEDDIC Question — $1.22M and Growing

Pattern: 4 deals worth $720K were lost specifically because prospects required MEDDIC-first positioning. A 5th deal — Darktrace ($500K) — is delayed, not lost, with an active path back via SPICED mid-year execution. In every case, the prospect didn't reject WbD's methodology — they needed MEDDIC and methodology. MEDDIC Powered by SPICED directly addresses this gap. Cerby ($100K) was lost when 1mind partner took the deal solo as a "MEDDIC shop" — even partner deals are affected.

CompanyAmountWhat They Said
JFrog$400,000$500M+ ARR, PLG-to-enterprise shift. "Preferred MEDDIC more central to training than SPICED."
Maxar$250,000CTO/CEO hard requirement: "MEDDIC is requirement" — wanted MEDDPICC-first, not overlay.
Okta$250,000Deal name was literally "MEDDIC Alignment." Champion not final decision-maker; consensus stalled.
Rakuten$120,000"MEDDIC — the CEO wanted a quick win." Existing customer choosing qualification speed over methodology depth.
Cerby$100,000"1mind will take solo — they are a MEDDIC shop, and the design element wasn't a strong enough fit."

The Pricing Signal — "3x Competitor"

Two deals ($437K) cited WbD pricing at approximately 3x competitor quotes. WP Engine ($250K, 500 CS reps, ACV $175K) said "price is about triple." Factorial ($187K, ACV $25K) lost for the third time on price — "3x too expensive." Both are mid-market companies where the cost-per-rep math doesn't work at WbD's current structure. This is a segment mismatch, not a global pricing issue.

Methodology Fatigue — A Retention Risk

Grain data reveals a pattern that extends beyond new business: prospects and customers cite "methodology fatigue" from cycling through frameworks (Challenger → MEDDIC → WbD) without sustained adoption.

"What we did at Calendly didn't stick. We had to keep coming back. It was a training event. It was operationalized — we built our Salesforce environment to model the bowtie workflow. But people didn't do SPICED on a call. That never stopped." — Amy McClain, Affirm | Describes prior $750K WbD engagement at Calendly

This insight is critical for product strategy: the market increasingly expects methodology to be embedded in tools (Salesforce, Gong, Gainsight), not delivered as training events. The Darktrace/Salesforce partnership discussion explicitly explored training Salesforce AI agents on SPICED — this is where the market is heading.

The Language Gap — What Customers Say vs. What We Say

What Customers Say
• "We need a sales methodology"
• "We need training and enablement"
• "Help us shorten our sales cycle"
• "Train our managers to coach"
• "Make our CRM reflect the methodology"
• "Not looking for soup to nuts — just the enablement piece"
What WbD Proposes
• "Revenue Architecture / Growth Architecture"
• "Growth Governance / Growth Guidance"
• "Diagnostic + Design + Deploy"
• "Full GTM methodology (not just sales)"
• "Bow tie model as operating system"
• "Monte Carlo analysis and growth thesis"

Scope creep tension (from Grain): Causeway/Rothschild explicitly said "we're not looking for full bow tie SPICED soup to nuts — the way in would be this enablement piece." People.ai asked WbD to NOT call SPICED a methodology and present it only as a "framework." The most successful engagements happen when WbD meets customers in their language first — ASCM's Bryan Miller, who deeply understands methodology, was won over precisely because he arrived speaking WbD's language already.

By Deal Owner

Pipeline Lost by Owner
Loss Reasons by Owner
Owner Breakdown
Dan Smith
$2.98M
11 deals
Rachael Smith *
$1.34M
5 deals
Mike Boogaard
$1.21M
5 deals
Matt Kaminski
$940K
4 deals
Betsy Peters
$700K
4 deals
Other
$1.19M
5 deals

Rachael Smith is no longer active in HubSpot. Her 5 deals ($1.34M) — Contentful, Digital Realty, Lambda Labs (x2), FrontApp — are orphaned. Pipeline ownership needs reassignment for any recovery efforts.

All Strategic Deals — Q4 2025 + Q1 2026

34 deals with adjusted amounts above placeholder threshold. Sorted by loss reason, then value.

# Company Deal Owner Amount Status Loss Reason Detail Link
Went Dark — 5 deals · $1.46M
1 Digital Realty Trust Methodology Rollout Rachael Smith * $400,000 Lost Went Dark No response post-GTM reorg. Past methodology rollouts stalled — likely internal fatigue. HS→
2 Postman Methodology Transformation Dan Smith $375,000 Lost Went Dark CRO on paternity leave during eval. 700 GTM, $200M+ ARR, 5 vendors. Requirements shifted. HS→
3 Okta MEDDIC Alignment Dan Smith $250,000 Lost Went Dark Champion not final decision-maker. Lengthy consensus cycle stalled — no executive sponsor. HS→
4 Obsidian Security GTM Efficiency Program Betsy Peters $210,000 Lost Went Dark Growth decelerating 3x→2x. GTM efficiency pressure rising but no champion materialized. HS→
5 Siemens Manager Training Mike Boogaard $150,000 Lost Went Dark Gone dark. No response after first email referral from Andrew. HS→
External Event — 4 deals · $1.35M — Uncontrollable
6 Metronome Revenue Architecture Dan Smith $386,000 Lost Acquisition Acquired by Stripe. All vendor engagements cancelled. HS→
7 Wiz UK Training Mike Boogaard $166,000 Lost Acquisition Google acquisition froze all vendor procurement. Not a competitive loss. HS→
8 Teknor Apex Mothership Transformation Betsy Peters $150,000 Lost Cancelled March project cancelled. 101-year-old manufacturer — sales restructuring never happened. HS→
9 Confluent Sales Transformation Dan Smith $100,000 Lost Acquisition Company acquired by IBM. All vendor evaluations halted. HS→
MEDDIC-First — 5 deals · $1.22M
10 Darktrace Methodology Transformation Matt Kaminski $500,000 Delayed MEDDIC-First 1,700+ GTM, US IPO prep. Will execute SPICED mid-year, not at SKO. Active path back. HS→
11 JFrog Enterprise Training Mike Boogaard $400,000 Lost MEDDIC-First $500M+ ARR, PLG→enterprise shift. Wanted MEDDPICC more central to training than SPICED. HS→
12 Maxar Technologies Subscription Model GTM Dan Smith $250,000 Lost MEDDIC-First MEDDIC hard requirement from CTO/CEO. Wanted MEDDPICC-first, not methodology overlay. HS→
13 Rakuten Methodology / MEDDIC vs. SPICED Dan Smith $120,000 Lost MEDDIC-First CEO wanted MEDDIC as a "quick win." Existing customer chose qualification speed over methodology depth. HS→
14 Cerby 1mind / WbD Joint Sales Dan Smith $100,000 Lost MEDDIC-First 1mind took solo — MEDDIC shop. WbD design element wasn't a strong enough fit alone. HS→
Competitor — 4 deals · $1.20M
15 First Advantage Sales & CS Training Dan Smith $500,000 Lost Value Selling Lost to Value Selling — incumbent from acquired Sterling. 551 GTM reps. HS→
16 Contentful CKO & Quarterly Training Rachael Smith * $400,000 Lost Sandler CRO had longstanding Sandler relationship. WbD runner-up of 8 vendors — "ran the best sales cycle." HS→
17 FrontApp Sales Methodology Rollout Rachael Smith * $150,000 Lost Sandler Lost to Sandler. No enablement person for 2 years — budget constraints tipped decision. HS→
18 Dropbox Manager Coaching Rachael Smith * $150,000 Lost Competitor Existing customer. Manager coaching deal did not progress. HS→
No Priority — 5 deals · $925K
19 McKesson Growth Strategy Phase 2 Dan Smith $220,000 Lost No Priority Phase 2 lacked urgency after Phase 1. No champion driving continued investment. HS→
20 Frontline Education K-12 Revenue Transformation Betsy Peters $190,400 Lost No Priority No critical event. New management — urgency before August slowdown never materialized. HS→
21 Lambda Labs Right Side Playbook Rachael Smith * $155,000 Lost No Priority Post-sale friction consumed bandwidth. Data center financing took priority. HS→
22 Bitso B2B Payments GTM Dan Smith $150,000 Lost No Priority Not priority for sales leadership despite 70% growth. No RevOps team to drive internally. HS→
23 SpaceX Enablement for Resellers Dan Smith $100,000 Lost No Priority EVP doesn't believe skills training will get quick wins for channel partners. HS→
Rescoping — 3 deals · $650K
24 Lambda Labs SOW 4 — Coaching Rachael Smith * $350,000 Delayed Rescoping Placeholder SOW being rescoped. Lambda pivoting to cloud, targeting $1B ARR. HS→
25 ABC Fitness Revenue Ops Restructure Matt Kaminski $150,000 Lost Rescoping $350M company, 38% onboarding churn. Board couldn't reach consensus on direction. HS→
26 TD SYNNEX Channel Enablement Matt Kaminski $150,000 Delayed Rescoping 3rd-party agent; potential need late Fall. Parked, not dead. HS→
Champion Left — 3 deals · $460K
27 Cognism Training Mike Boogaard $180,000 Lost Champion Left Champion left, new management. $80M+ SaaS, 120 reps — deal died with leadership change. HS→
28 Tango Analytics Growth Strategy Betsy Peters $150,000 Lost Champion Left Champion left during layoffs (20 cut). Recruiting new CS head — org instability killed momentum. HS→
29 Zafin SPICED Follow-On Dan Smith $130,000 Lost Champion Left DM left for health reasons. New leader not going in this direction. HS→
Price — 2 deals · $437K
30 WP Engine Sales Training — SPICED Dan Smith $250,000 Lost Price Price ~3x competitor quote. 175K customers, 500 CS reps — wanted SPICED but couldn't justify cost. HS→
31 Factorial Training (3rd attempt) Mike Boogaard $187,000 Lost Price 3rd time WbD lost here. Price 3x too high — ACV only $25K, cost/value mismatch for their scale. HS→
DIY / Access — 2 deals · $395K
32 Check Point SKO Mike Boogaard $295,000 Lost In-House Decided to do SKO in-house. Building internal enablement capability. HS→
33 DXC Technology New Deal Dan Smith $100,000 Lost No Access Not able to access decision maker. Wanted quote via email without discovery — not a fit. HS→
Access / Fit — 1 deal · $140K
34 Five9 Advisory Access Pass — SKO Matt Kaminski $140,000 Lost Limited Access Limited access to execs. Existing customer but couldn't progress advisory engagement. HS→

Data Quality Note: An additional ~90 deals in this period were closed at exactly $50,000 with no line items, no stage progression, or marked as duplicates/not-ICP. These represent pipeline hygiene opportunities, not strategic losses. Examples: Adevinta ("Deal created without any activity"), Nium ("DUPLICATE"), Keralty ("Not ICP"), GRO ("Jacco Keynote / Not an Opp"). Consider a CRM cleanup initiative to improve forecasting accuracy.

Recoverable Pipeline

$1.0M across 3 deals with active recovery paths:

• Darktrace ($500K) — Confirmed SPICED mid-year execution. Matt Kaminski actively working Salesforce partnership angle with SPICED-trained AI agents.

• Lambda Labs SOW 4 ($350K) — Rescoping to new project. Lambda targeting $1B ARR with cloud pivot.

• TD SYNNEX ($150K) — 3rd-party agent; potential need late Fall 2026.

Recommended Actions

01
Launch MEDDIC Powered by SPICED as a named offering
5 deals ($1.22M) lost specifically because prospects needed MEDDIC centrality. Position SPICED as the methodology layer that makes MEDDIC operationally effective — not a replacement. Darktrace ($500K) is the first target with this positioning.
Addressable: $1.22M in lost + future MEDDIC-first pipeline
02
Build "went dark" executive re-engagement playbook
5 deals ($1.46M) went dark — the #1 loss category. Postman ($375K, CRO returned from leave) and Okta ($250K, needs executive sponsor) are both recoverable with senior-level outreach. Implement a 90-day structured re-engagement cadence.
At risk: $1.46M with no current recovery path
03
Embed methodology in tools, not just training events
Grain data shows the #1 customer concern: "will this stick?" The Affirm insight ($750K at Calendly "didn't stick") and the Darktrace/Salesforce AI agent discussion point the same direction — methodology must be embedded in Salesforce, Gong, and Gainsight to be durable.
Strategic: Differentiator against Sandler and MEDDIC-only vendors
04
Reassign orphaned pipeline and review owner distribution
Rachael Smith's 5 deals ($1.34M) need immediate reassignment. Digital Realty ($400K) and Lambda ($505K across 2 deals) are the highest priority. Dan Smith carries 36% of total lost pipeline by value — assess capacity and support.
At risk: $1.34M with no active owner
05
Develop mid-market pricing tier for sub-$50K ACV accounts
Two deals ($437K) cited WbD at 3x competitor pricing. Both were mid-market (ACV $25K-$175K) where full-service engagement pricing creates mismatch. Consider scaled or self-serve options for this segment.
Addressable: $437K lost + mid-market segment expansion
06
CRM pipeline hygiene initiative
~90 deals at exactly $50K with no activity, duplicates, or not-ICP flags create noise in pipeline reporting. Implement deal creation standards (minimum fields, stage gates) to improve forecast accuracy and ELT visibility.
Operational: Better forecasting and pipeline signal quality

Source: HubSpot CRM + Grain AI Call Intelligence | Data pulled April 1, 2026 | Internal — Confidential

* Rachael Smith marked inactive in HubSpot. Deal values from HubSpot amount field. Loss reasons classified using HubSpot closed_lost_reason + Grain SPICED fields.