Travelers — Deal Risk Assessment

Account / Deal

Travelers — Travelers Opal 2026

Owner

Jen Oliver (AE) · Conor Leary (overlay)

Stage / Target Close

Proposal 2026-03-27

Size / Strategic Importance

$309,000 base ($500K upside) · High

Key Champions

Betsey Shannon (marketing owner, highly engaged) · Dave Morgan (use case/ROI orchestrator, driving concurrent workstreams)

Current Status

ROI working session completed 2/19 — bottom-up approach agreed. Legal actively redlining contract; redlines expected back this week. TechGov/vendor approval in flight. Shafkat–Jim O'Brien exec meeting this Thursday. Four parallel workstreams: legal, TechGov, ROI, dollar-threshold approval.

ID	Category	Risk	Evidence	Impact	Plays	Owner & By When
R1	Paper	Vendor approval process is opaque and slow — could take 1+ month Known	2/13 sync: "could take 1+ month with no visibility into steps." A $0 POC started in October still isn't through architecture review. Neither Conor nor Jen has visibility into approvers or status.	Critical path blocker. March 27 close impossible if vendor approval runs its historical pace.	P1 P2 P3	Jen — Patrick West → Andrew Jaworski exec push, this week
R2	Paper	Dollar threshold may trigger higher/slower approval path Known	2/19 ROI session: Dave flagged dollar thresholds require different approval. 2/12: procurement flagged credit rollover as non-starter.	Unknown escalation path could add weeks. Combined with R1, creates compounding paper risk.	P3 P6 P11	Conor/Jen — surface thresholds once pricing finalized
R3	Paper	Legal redlines returning with unknown scope Known	2/19: attorney completed redlining, returning early this week. Attorney already flagged technical question on AI infrastructure (Gemini).	Extensive redlines = multi-week legal back-and-forth. AI-specific terms likely contentious for FSI.	P6	Jen — receive and triage redlines this week
R4	Value	ROI calculation gated on Betsey's usage data Known	2/19: "Betsey's team providing usage data by Monday EOD." Betsey's original scoring data was lost (save issue). Mark cannot build value calculation without user counts and frequency.	Any delay in usage data delays the entire business case presentation to Dave and blocks commercial progression.	P4	Conor — follow up with Betsey if not received, 2026-02-25
R5	Commercial	Credit rollover terms non-negotiable for Travelers procurement Known	2/12: "Dave flagged procurement team does not accept use-it-or-lose-it terms. Will introduce procurement team to discuss."	Could stall commercial negotiation at procurement stage even after business case is approved.	P6 P11	Jen/Conor — prepare term alternatives before procurement engagement
R6	Political	Dave Morgan's interpersonal dynamics slow internal progress Known	2/13: "Dave is not forthcoming with details, his internal relationships may actually slow things down (people don't respond well to him)." Betsey is "intimidated by Dave."	Internal alignment and vendor approval acceleration depend on working around Dave's domain, not through him.	P2 P3	Jen — Andrew Jaworski path bypasses Dave's bottleneck
R7	Paper	FDE classification unresolved — may trigger separate SOW cycle Known	2/13: If FDE is classified as IT Services (not bundled in Advanced), Travelers requires their services SOW template, adding procurement delay. Conor owns resolution via Suzanne.	Separate services classification = additional procurement review cycle on top of existing paper workstreams.	P6	Conor — resolve via Suzanne, this week
R8	Timing	Architecture review backlogged — 1-2 month estimate Known	2/12: "AI vendor approval timeline 1-2 months. Architecture review team backlogged with AI approvals." Strong business case is the stated accelerator.	Even with exec push, architecture review unlikely to compress below 3-4 weeks. March 27 is at risk.	P1 P2	Jen — exec acceleration via Jaworski/Patrick West

[P11] Prepare credit rollover term alternatives for procurement conversation.
Owner: Conor/Jen · When: before procurement introduction
[P3] Surface dollar-threshold details from Dave or Betsey — what number triggers higher approval?
Owner: Conor · When: during ROI readout
[P8] Validate multi-agent workflow credit counting and provide explicit answer per 2/12 commitment.
Owner: Conor · When: this week
Connect Dave with Phil Scone (BSI) for GEO/AEO reference — routes through Danielle/analytics team.
Owner: Mark · When: next week
[P4] Schedule ROI readout session once Mark completes value calculation.
Owner: Conor · When: once usage data received

Exec Escalation Required

Top Risks Requiring Exec Help (Max 3)

R1 — Vendor approval process is opaque, could take 1+ month, no visibility into approvers
R8 — Architecture review backlogged with 1-2 month estimate; strong business case is stated accelerator
R6 — Dave Morgan's interpersonal dynamics are slowing internal progress; need parallel exec path

What We've Already Done to Mitigate

Shafkat connected with Jim O'Brien at workshop — exec meeting scheduled this Thursday
Jen engaging Patrick West for Andrew Jaworski (Dave's boss) introduction
Legal actively redlining contract; TechGov submitted
ROI working session completed; bottom-up approach agreed with Dave and Betsey

Specific Requests from ELT / SLT

Shafkat to meet Jim O'Brien Thursday — prep call Tuesday 4:30 PM ET with Betsey, Deb Breines, Conor, Jen. Need Shafkat briefed on: (1) Jim's role spanning digital marketing + business insurance, (2) vendor approval acceleration as the ask, (3) Opal in OKRs framing.
Patrick West to introduce Andrew Jaworski to Jen this week — framed as "we lack clarity on where vendor approval stands and risk missing Q1 close."