Dell — Deal Risk Assessment

February 24, 2026 · Dell Opal 2026 · Risk Assessment & Mitigation Plan
Deal Snapshot
Account / Deal
Dell — Dell Opal 2026
Owner
Matt Emerson Payne (AE) · Conor Leary (overlay)
Stage / Target Close
Proposal / 2026-03-27
Size / Strategic Importance
$200,000 / High (enterprise new logo, Jasper displacement, CMS cross-sell)
Key Champion(s)
Evan Greenbaum (responsive, NYC-based, Jasper product owner) · Ryan Schaaf (MarTech Innovation lead, Optimizely “fanboy”)
Current Status
Deal is stalled. Last customer meeting was 41 days ago (1/14 handoff). AE handoff from Cuneyt to Matt/Conor occurred but no evidence of follow-through. POC use cases undefined. NYC onsite not scheduled. Credit usage dropped post-December workshops.
Total Risks
8
across 6 categories
Known Risks
6
evidence documented
Assumed Risks
2
inferred from signals
Play Code Legend
CodePlay
P1ELT exec bridge (C-suite ↔ C-suite)
P2SLT bridge (VP/Director ↔ VP/Director)
P3Back-channeling / political intel
P4Value / business outcomes workshop
P5Technical / architecture risk session
P6Commercial alignment session
P7On-site
P8Own internal business case structure
P9Customer-facing exec 1-pager
P10Internal exec briefing 1-pager
P11Pricing / term levers
Risk Register
ID Category Risk Evidence Impact Plays Owner & By When
R1 Timing 41 days since last customer meeting — deal is stalled
Known
  • Last meeting note: 2026-01-14 (handoff call)
  • No customer-facing activity since
  • December workshop momentum lost
 March 27 close is not achievable without immediate re-engagement. Deal may already be lost to competitor. P7 P4 Matt/Conor — re-engage Evan immediately, this week
R2 Value POC use cases still undefined
Known
  • 1/14 handoff: “POC use cases still undefined — need Dell commitment to move forward.”
  • Next step was collaborative use case definition. No evidence it occurred.
 No POC scope = no business case = no path to close. Without defined use cases, Dell has nothing to evaluate. P4 P5 Conor — propose content operations POC scope during re-engagement
R3 Political AE handoff execution unclear — 41-day silence
Assumed
  • 1/14: “Matt to email Evan introducing Conor as new Opal lead.”
  • No subsequent meeting notes confirm this happened.
  • No Evan re-engagement documented.
 If Evan hasn’t heard from Optimizely in 6 weeks, trust eroded and competitors may have advanced. P7 P3 Matt — confirm handoff status and send intro email if not done, immediately
R4 Technical Credit usage dropped post-workshop — low engagement
Known
  • 1/14: “usage dropped post-workshop — Dell team not self-exploring.”
  • December workshops well-received but no sustained adoption.
 Low platform engagement = low internal advocacy. Evan cannot champion what his team isn’t using. P4 P5 Conor — after re-engagement, schedule hands-on use case session
R5 Paper Paper process completely unknown
Known
  • Deal file: Paper Process = “Unknown.”
  • No signals from any meeting on procurement, legal, or security requirements.
 Enterprise deal with unknown procurement = unpredictable close timeline. Could add months. P3 P8 Conor — surface paper process during re-engagement call
R6 Commercial Jasper is incumbent and paying — switching cost is real
Known
  • 1/14: “Jasper: Paying customer.” Dell has existing budget allocated to Jasper.
  • Jasper pain (limited brand guidelines) documented but not reinforced recently.
 Status quo bias. If Opal evaluation stalls, Dell renews Jasper by default. P4 P9 Conor — position content operations differentiation vs. Jasper during POC scoping
R7 Political No engagement above Evan since handoff
Assumed
  • Decision process: Evan → Ryan → Liana/Liz for budget.
  • Ryan described as “fanboy” but no contact since December.
  • No EB engagement documented.
 No budget conversation happening. No internal business case being built above Evan’s level. P2 P3 Matt/Conor — re-engage Ryan Schaaf after Evan reconnect
R8 Value Insufficient discovery — vault data is thin
Known
  • Only 2 meeting notes exist for Opal track.
  • MEDDPICC metrics limited to “10% YoY reduction.”
  • No validated pain beyond initial handoff intel.
  • Workshop outcomes not documented.
 Cannot build compelling business case without deeper discovery. Flying blind on decision criteria and process. P4 P8 Conor — run proper discovery during re-engagement
Mitigation Plays — Cross-Mapping
P4
Value / business outcomes workshop
Mitigates: R1 R2 R4 R6 R8 — re-engagement + POC scoping + discovery
P7
On-site
Mitigates: R1 R3 — NYC onsite with Lauren’s Opal team (Evan is NYC-based)
P3
Back-channeling / political intel
Mitigates: R3 R5 R7 — confirm handoff status, surface paper process, Ryan Schaaf engagement
P8
Own internal business case structure
Mitigates: R5 R8 — build business case framework proactively given thin data
P9
Customer-facing exec 1-pager
Mitigates: R6 — Opal vs. Jasper differentiation doc for internal circulation
Action Plan — Must-Do Priorities
1 P3 Confirm AE handoff was executed — if not, send Evan intro email immediately
Linked Risks
R1 R3
Owner
Matt Emerson Payne
Due
2026-02-25
41 days of silence. If handoff email was never sent, deal is dead until contact is re-established.
2 P4 Schedule re-engagement call with Evan — propose content operations POC scope
Linked Risks
R1 R2 R4 R8
Owner
Conor
Due
2026-02-28
Highest single-action impact. Addresses staleness, defines POC, restarts engagement, and surfaces current competitive state.
3 P7 Schedule NYC onsite with Lauren’s Opal product team
Linked Risks
R1 R3
Owner
Conor / Matt
Due
2026-03-07
Evan is NYC-based. Opal team is NYC-based. In-person builds trust and differentiates from Jasper’s remote-only engagement. Was a planned next step from 1/14 that never happened.
4 P3 Re-engage Ryan Schaaf — get current intel on Dell’s evaluation status
Linked Risks
R7
Owner
Matt
Due
2026-03-03
Ryan is the internal champion above Evan. Need to know: is Dell still evaluating? Has Jasper renewed? Has another competitor entered?
Action Plan — Secondary Tasks
Internal Exec Support
No ELT/SLT support required at this time. Priority is re-establishing basic contact and defining POC scope. Exec engagement (P1/P2 to Liana or Liz Matthews) should be planned once Evan and Ryan are re-engaged and POC is in flight.