Travelers — Deal Risk Assessment

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. April now confirmed new target.	P1 P2 P3	Jen — confirm Patrick West → Andrew Jaworski intro occurred; if not, re-engage
R2	Paper	Dollar threshold may trigger higher/slower approval path Known	2/19 ROI session: Dave flagged dollar thresholds require different approval but did not disclose amounts. 2/12: procurement flagged credit rollover as non-starter.	Unknown escalation path could add weeks. Combined with R1, creates compounding paper risk. Deal structure may need to be architected under threshold.	P3 P6 P11	Conor/Jen — surface thresholds during pricing presentation
R3	Paper	Legal redlines returning with unknown scope — timeline slipped twice Known	2/19: attorney completed redlining, returning "early this week." 3/5: Yolanda revised to 2 weeks out — attorney "really, really busy." High-level guidance ~3/12; full redlines ~3/19. Attorney already flagged technical question on AI infrastructure (Gemini). Timeline has slipped twice from original estimate.	Extensive redlines = multi-week legal back-and-forth. AI-specific terms likely contentious for FSI. Each slip tightens April 8 submission window.	P6	Jen — receive and triage redlines ~2026-03-19
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). 3/5: Usage data received; 54% efficiency benchmark adopted. Mark's calculation: 31K hours, 16.3 FTEs, $2.47M savings. Dave/Betsey validating row-by-row (week of 3/9).	Partially mitigated — benchmark adopted and spreadsheet in progress. Row-by-row validation is the remaining gate before pricing presentation. Any delay cascades to April 8 submission.	P4	Conor — confirm Dave/Betsey working session completed week of 3/9
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." Procurement lead identified: Eric Drouin. Signatory identified: Deborah Strong (Technology CFO) — signed 2025 renewal and upsell.	Could stall commercial negotiation at procurement stage even after business case is approved. Eric Drouin engagement needed with term alternatives ready.	P6 P11	Jen/Conor — prepare term alternatives before Eric Drouin 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." 3/5: Dave engaged methodically — positive signal, but his process-driven pace compounds timing risk.	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. Must resolve before pricing presentation.	P6	Conor — confirm FDE resolution status before pricing presentation
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. Dave is "following up" on status but no named contact (2/19).	Even with exec push, architecture review unlikely to compress below 3-4 weeks. April close at risk if not initiated immediately.	P1 P2	Jen — exec acceleration via Jaworski/Patrick West; confirm status
R9 NEW 3/5	Commercial	Yolanda pushing for POC/POT instead of direct commercial path Known	3/5: Yolanda floated POC as alternative path, citing "very new development" and pricing model not yet solidified. Richard pushed back: "we have no hesitation on presenting pricing." Yolanda asked team to discuss internally and share preferred path at next working session. 3/13: Yolanda shifted from POC blocker to commercial negotiator — now negotiating terms (underutilization risk, monitoring period, Y3 credit). Positive engagement shift.	POC/POT risk partially mitigated by Yolanda's shift to commercial negotiation (3/13). Still monitor — could resurface if pricing impasse develops.	P6 P11	Conor/Richard — hold firm on direct commercial path; Yolanda now engaging on terms
R10 NEW 3/5	Commercial	Dave focused on minimum tier commitment, not total ROI Known	3/5: "Where I'm mostly focused is trying to figure out usage so we understand what we would potentially commit to with regard to usage volumes — what would our minimum tier be?"	Signals potential desire to start smaller than $309K scope. May need tiered pricing options or phased commitment structure to maintain value while meeting Dave's risk tolerance.	P6 P11	Conor — prepare tiered commitment options alongside full proposal
R11 NEW 3/5	Commercial	Module-dependent use case sequencing creates over-commitment perception Known	3/5: Dave flagged that not all modules can leverage Opal simultaneously — some use cases available in "next 3 months," others ramp later as CMS12 custom tooling (Kim's team) becomes available. Scope includes 20% wildcard buffer beyond 36 identified use cases. 90%+ of use cases confirmed on CMS12 — no CMS13 migration required.	Pricing a full 36-use-case scope from day 1 could lead Travelers to feel over-committed vs. actual day-1 value. Dave may use this to argue for smaller initial commitment.	P6 P11	Conor — model phased/ramped commitment structure; sequence use cases into launch vs. 3–6 month tranches in pricing presentation
R12 NEW 3/13	Commercial	$618K price triggers sticker shock — Dave benchmarking against raw LLM costs Known	3/13: Dave: "Major league sticker shock... not in a small way." Comparing Opal pricing for 12 users against Atlassian AI for 12,000 users. Plans to benchmark with internal AI group using direct Anthropic/OpenAI/Gemini agreements. Dave knows Opal uses Gemini — will compare credit pricing against raw token pricing.	If Travelers' AI group benchmarks Opal credits against raw token pricing, the orchestration markup will appear steep. Price competition is not against other products — it's against raw model access. Must reframe value of harness, tooling, FDE, and support.	P6 P11	Conor — prepare orchestration value justification (harness, tooling, FDE, support) before Hartford 3/18; Jen arrange Shaf technical call
R13 NEW 3/13	Commercial	Credit underutilization risk — Yolanda demanding contractual protection Known	3/13: Yolanda does not want to pay for unused capacity. Matt offered Y1→Y2 rollover (requires CFO approval). Yolanda countered with Y3 credit against final invoice.	New commercial concession required. Rollover + Y3 credit is beyond standard terms — needs CFO sign-off on Optimizely side. If denied, could stall procurement.	P6 P11	Matt — take rollover proposal to CFO; Conor — prepare fallback positions

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
R12 — $618K sticker shock; Dave benchmarking against raw LLM costs via internal AI group. Must reframe orchestration value before Hartford 3/18.

What We've Already Done to Mitigate

Shafkat met Jim O'Brien (~late Feb) — outcome TBC; confirm whether vendor approval was discussed
Jen engaging Patrick West for Andrew Jaworski (Dave's boss) introduction — status TBC
Legal actively redlining contract; TechGov submitted; architecture review still in flight
ROI working session completed (2/19); 54% benchmark adopted (3/5); Dave/Betsey validating spreadsheet row-by-row
Richard pushed back on Yolanda's POC/POT trial balloon at 3/5 — Yolanda now engaging commercially (positive shift per 3/13)
Pricing presented 3/13 ($618K/year); Matt offered Y1→Y2 credit rollover (CFO approval pending)

Specific Requests from ELT / SLT (Updated 2026-03-16)

Shafkat/Jim O'Brien — confirm outcome of exec meeting; if vendor approval not yet raised, determine whether a follow-up is appropriate. Framing: "April close requires architecture review acceleration."
Patrick West → Andrew Jaworski — confirm introduction occurred; if not, re-engage. Framing: "we lack clarity on where vendor approval stands and April close is at risk."
Richard — maintain direct commercial path at Travelers working sessions; Yolanda now negotiating terms (positive), but POC could resurface if pricing impasse develops.