Likelihood (1–5) × Impact (1–5) = Score. Critical ≥ 20, High ≥ 12, Medium ≥ 6.
| ID | Category | Risk | Evidence | Impact | Plays | Owner & By When |
|---|---|---|---|---|---|---|
| R1 | Paper |
Paper process not started — procurement contact identified, parallel processing rejected
Known |
• Andrew Grabell identified as procurement signatory from October renewal. Lucy Fan was IC; status uncertain (“there might be some issues”). • Existing MSA product supplement likely contains AI language — if confirmed, deal reduces to agreeing a number (still unconfirmed). • 3/2 (Dave Chiang backchannel): Procurement team understaffed, going through cuts. Escalation always required to move contracts. • 3/4 (Pragya email): Pragya explicitly rejected order form and pre-staging approach: “We’re still in the evaluation phase and not yet ready to move forward with the order form or procurement steps.” • 3/9: No change — Pragya confirmed all contract conversations route through her. Paper process start gated entirely on Vi providing budget direction (~March 23 earliest). |
Parallel procurement is off the table. Paper process cannot start until Vi gives budget direction (~March 23). This leaves fewer than 5 business days to execute the full paper process before March 31 — making March 31 contingent on a frictionless procurement run. |
P3
P6
|
Conor — do NOT send further procurement materials until Pragya initiates; confirm AI language in MSA product supplement (still unconfirmed); monitor Lucy Fan status; be ready to execute paper process at speed post-Vi approval |
| R2 | Timing |
Extreme timeline compression — Vi unavailable until ~March 23
Known |
• Original sequence: pilot complete March 6 → business case March 9–12 → Vi readout March 13 → close March 31. • 3/9: Vi at Enterprise Connect this week, Zoom off-site next week. Earliest realistic Vi engagement is ~March 23, leaving only 6 business days before March 31. • Pragya confirmed budget direction from Vi must precede Opal business case presentation — sequential dependency, not parallel. • March 13 Vi readout target is effectively dead. |
Zero-margin timeline. Vi’s two-week unavailability eliminates all buffer. Business case presentation cannot even begin until Vi provides budget direction, then procurement still needs to process. March 31 close requires near-perfect execution in the final week. |
P6
P8
|
Conor — maintain weekly checkpoint cadence; escalate any slip immediately. Recalibrate internal expectations: March 31 is now best-case, not baseline. |
| R3 | Political |
Single-threaded through Pragya Singh — champion re-engaged but gatekeeping intensified
Known |
• Pragya is the only path to Vi Chau. No direct Optimizely-to-Vi relationship built. • 3/4: Pragya declining even 15-minute calls. Independently shared pricing with Vi without Conor’s input — no procurement defensibility backboard in place. • 3/5: Brandon Renoe confirmed Pragya’s slow responsiveness is a general communication pattern, not Opal-specific. Brandon now actively willing to push internally on Opal urgency. • 3/9: Pragya accepted a live 1:1 call (positive reversal). Engaged substantively on pricing, acknowledged bundle value. However, explicitly requested ALL pricing/contract conversations route through her only. Also conducting full audit of Optimizely contract utilization — building comprehensive case for Vi rather than evaluating Opal in isolation. |
Champion engagement has stabilized (call accepted, constructive tone, committed to pushing internally on March timeline). Gatekeeping intensified — Pragya wants to be sole commercial conduit. Contract audit is double-edged: could strengthen the case for Vi or surface underutilization grievances. |
P1
P2
P3
P7
|
Conor — build parallel path via Kim/Alex CMO summit mid-March; Patrick to explore Alex Kim relationship. Brandon Renoe as supplementary internal advocate. Send Seattle in-person meeting email to Vi’s team (Conor + Patrick framing Amazon visit). Activate Rupali → Vi channel. Provide Content Recs info promptly — Pragya’s contract audit is an opportunity to demonstrate transparency. |
| R4 | Technical |
Pilot scope risk — all three agents validated (COMPLETE)
Known |
• Pragya required ALL THREE agents validated before building executive case for Vi. • 2/27: David Tice (sole evaluator for Content Audit and GEO agents) confirmed no defined success criteria — entirely subjective. • Conor shared evaluation rubric with David to create structure. • Pilot complete March 6 — all three agents delivered. |
Risk materially reduced — pilot complete and delivered. Success criteria framework provided to David. Risk now shifts to how David’s qualitative feedback influences Pragya’s executive case framing. |
P5
P8
|
Conor — monitor how David’s subjective assessment feeds into Pragya’s executive case; ensure evaluation rubric anchors any formal POC feedback |
| R5 | Political |
Economic buyer (Vi Chau) not directly engaged — budget severely constrained, all outreach failing
Known |
• Path is Pragya → Alex Kim → Vi — executive triangle active but indirect. • 3/2 (Dave Chiang backchannel): Vi’s budget cut by >50% after working media transferred to Kim. Remaining budget is headcount + partner spend only. Must defund something existing or escalate to Eric/Michelle for incremental budget. Vi evaluates on hard ROI, MRR-based metrics: top-line MRR growth and churn savings. Cost efficiency is second tier. Q4 fell short, pressure carrying into Q1. • 3/4: Alex’s email to both Vi and Kim received zero response. Rupali → Vi channel being activated (both Seattle, have met previously). • 3/5: Brandon confirmed Vi and Kim “don’t really see eye to eye.” Complicates executive triangle strategy. • 3/9: Vi at Enterprise Connect this week, off-site next week. Pragya hasn’t asked Vi about Alex meeting yet — will ping him but timing is very tight. Budget discussions happening but unresolved. Pragya explicitly stated budget direction must come before she can present the Opal plan. Marketing (Marla) unlikely to accelerate — felt evaluation was “too rushed.” |
EB engagement minimal and all outreach channels failing. Budget severely constrained (>50% cut). Current P0 “cost savings” positioning misaligns with Vi’s actual evaluation framework (hard ROI, MRR growth, churn savings). Kim-Vi misalignment complicates executive triangle. Marketing budget inclusion — previously the strongest path to making the deal digestible for Vi — is effectively off the table for Q1. |
P1
P7
P9
|
Conor/Patrick — reframe business case to lead with MRR impact / churn savings (Vi’s mandates), not cost savings. Prep exec outreach briefing for Kim/Alex CMO summit. Pursue marketing inclusion aggressively — Kim’s budget is most viable funding path. Identify Hugo Refuse (Kim’s new growth leader) as potential marketing engagement unlock. Activate Rupali → Vi as supplementary exec channel. Execute Seattle in-person play. 3/9: Vi/Alex meeting still not requested — follow up with Pragya mid-week. |
| R6 | Technical |
CMP adoption struggles could undermine Opal positioning
Known |
• Only Siobhan fully adopted CMP, rest of team struggling. • Opal positioned as CMP adoption accelerant. • Marketing has opted out of initial pilot — CMP adoption risk is less direct for current $250K deal scope. • If team associates Optimizely with difficult tools, Opal pitch loses credibility. |
Opal framed as solution to CMP adoption problem — but if adoption problem is deeper (product-market fit, training, workflow), adding Opal compounds complexity rather than solving it. Risk reduced since marketing opted out of initial pilot. |
P4
P5
|
Conor — frame Opal value independent of CMP in business case; ensure pilot agents don’t depend on CMP proficiency |
| R7 | Political |
Internal experimentation friction and leadership skepticism
Known |
• Open friction between Pragya and Brandon. Michael Lam exploring analytics as replacement for experimentation. • 2/27: TK Marks confirmed trust in experimentation is “very fractured.” Vi never experienced the $9–10M lower-funnel testing revenue under Wendy Berg. • TK pursuing pricing page analysis as potential proof point for experimentation value story. • TK and Brandon describe themselves as “on an island” with no leadership mandate. |
Negative experimentation sentiment is cultural, not just political. If experimentation skepticism contaminates the Opal evaluation, the deal faces headwinds from the platform relationship itself. |
P3
P4
|
Patrick — manage Brandon relationship; Conor — ensure Opal narrative is independent of experimentation program health; monitor TK’s pricing page analysis results as potential proof point |
| R8 | Political |
Marketing team opted out of pilot — budget contribution off table for Q1
Known |
• 3/5 (Brandon Renoe sync): Marketing team decided not to participate in initial pilot but wants involvement later. • 3/9 (Pragya): Marla’s team felt the Opal evaluation was “too rushed.” Pragya open to influencing marketing to reconsider but made no commitment. • Conor repositioned marketing inclusion as a way to share the budget burden (50/50 split reducing Vi’s portion). Pragya acknowledged but did not commit. • Hugo Refuse identified as Kim’s new growth leader (ex-Cisco/Microsoft) — potential future re-entry point. |
Deal is now $250K (online team only). No realistic path to marketing budget contribution by March 31. Marketing budget inclusion — previously the strongest path to making the deal digestible for Vi — is effectively off the table for Q1. |
P3
P7
|
Conor — do not pressure Marla further; keep marketing door open for post-close expansion. Re-evaluate whether $250K can close without marketing — focus exclusively on Vi’s online team budget path. Hugo Refuse remains an untapped marketing re-entry point for future phase. |
| R9 | Platform |
Account frustration accumulating — no visible improvements post-renewal
Known |
• 2/27 CMS cadence: Murali stated “close to 5–6 months since we signed the contract, and there were no improvements on the current state.” • Azure App Insights showing no measurable improvement at 95th percentile despite code optimizations. • AWS hosting question unresolved post-renewal — Murali warned “it will be the same discussion we’ll have again in 12 months or 18 months.” • Feb 20 security breach notification was generic with no Zoom-specific guidance — Pragya warned this could escalate to e-staff. |
Accumulating dissatisfaction with Optimizely platform/support quality creates headwinds for any new $250K investment. If Murali or Pragya frame the relationship as underdelivering to Vi, the Opal deal faces skepticism (“why spend more with a vendor who isn’t delivering on what we already have?”). |
P5
P3
|
Patrick — ensure full code audit delivery and review call happen within 48 hours of receipt; Matt Hurley — establish recurring performance metrics by next cadence call; Conor — monitor whether platform frustration bleeds into Opal evaluation conversations |
| R10 | Commercial |
Tool consolidation value narrative contradicted by domain expert
Known |
• 2/27 FDE alignment call: David Tice (sole evaluator for 2 of 3 POC agents) explicitly stated Opal is a “value-add, not a cost reduction thing.” • He warned: “I just wouldn’t pitch that” regarding tool consolidation. • Tool consolidation has been positioned as P0 value driver in business case. • Marcus Chen’s cost-neutral frame ($180K+ tool spend offset) depends on tools being replaceable — David explicitly contradicts this for Ahrefs, Lumar, and BrightEdge (except BrightEdge Content Advisor). |
The P0 value driver in the business case may not survive David’s evaluation feedback if he articulates this to Pragya. Business case narrative needs reframing from cost savings to productivity/value-add. If Vi hears “tool consolidation” and David’s feedback says otherwise, credibility gap emerges. |
P4
P8
|
Conor — reframe business case to lead with productivity/bottleneck elimination (David’s self-service SEO evaluation use case) as primary value driver; position tool consolidation as secondary/potential rather than P0; align with Pragya on narrative shift before business case iteration week |
| R11 | Commercial |
March 31 deadline urgency not internalized by Pragya — closing mechanism broken
New — 3/9 |
• 3/9: Pragya asked “what is the time limit you are driving this to be closed by?” — explicitly confirming she has not internalized March 31 as a firm deadline with commercial consequences. • She is aware of the bundle pricing but not the expiry mechanism. • Conor communicated the Q1 structure directly. Pragya responded positively (“that information is helpful”) and committed to trying to move the needle. • The fact this had to be explained in late early March suggests urgency has not been embedded in her internal advocacy. |
Pragya’s lack of urgency internalization means the commercial incentive (premium support + web experimentation free through March 31) has not been presented to Vi as time-sensitive. If Pragya does not communicate this deadline clearly to Vi during the ~March 23 window, the deal has no closing mechanism — Vi will see no reason to decide in 6 business days. |
P6
P11
|
Conor — send Pragya a concise written summary of the Q1 commercial structure for her to use verbatim with Vi: “$250K through 3/31 includes premium support ($285K) and web experimentation ($130K) — after 3/31, these are separate purchases at list price.” Make the urgency frameable, not salesy. |