This is not a hypothetical scenario. It is a structural timeline documented across 200+ go-to-market engagements in the $5M–$50M technology band. The specific events vary by company. The specific account names change. The specific dollar amounts differ. The pattern does not.
The VP Sales departs. What follows is not a leadership gap that a recruiting process will fill. It is the systematic, progressive exposure of every process dependency that was invisible while the VP was in the chair. The departure does not create new problems. It reveals old ones that the VP’s personal competence was masking.
Days 1–14: The Forecast Evaporates
The VP’s first standing meeting was the Monday forecast call. Without them, the CEO discovers that the forecast methodology does not exist as a system. The CRM contains pipeline data — deal values, stage labels, expected close dates. It does not contain a probability-weighted, stage-adjusted, historically-calibrated projection. That projection was produced weekly by the VP reviewing each deal, applying personal judgment informed by relationship context and pattern recognition, and committing a number they believed they could deliver.
The CEO steps into the gap. They spend 4–6 hours in the first week reviewing every deal in the pipeline, making their own probability assessments based on whatever information they can gather from AEs, and assembling a number they are willing to present to the board. It is not the VP’s forecast. It is the CEO’s best approximation — and both the CEO and the board know the difference.
Board confidence declines within the first reporting cycle. Not because the number is dramatically wrong. Because the source has changed, and the new source lacks the deal-level intimacy that made the previous forecast credible. The number might be right. The board cannot assess whether it is.
Days 15–30: Pipeline Hygiene Degrades
Pipeline reviews become informal. The VP ran them weekly with consistent time, consistent format, and consistent expectations. The team prepared because they knew the VP’s questions would be sharp, deal-specific, and consequential. A deal that could not withstand scrutiny was a deal that needed immediate attention.
Without the VP, the cadence breaks. Reviews happen when the CEO has time — which is increasingly rare as they absorb the VP’s other functions. Stage updates slow because nobody is asking about them. Aged deals accumulate because nobody is challenging them. The pipeline dashboard appears stable while the underlying data quality deteriorates day by day.
By day 30, the pipeline has accumulated 3–4 weeks of unexamined data. Deals that should have been restaged, removed, or escalated remain at their last-updated values. Coverage ratio on paper: stable. Actual pipeline health: declining.
Days 31–60: Key Accounts Surface as Risks
Two to three accounts that were personally managed by the VP request meetings. These are $40K–$120K ACV accounts representing 15–25% of total ARR. The VP attended their QBRs. They handled escalations personally. They maintained executive relationships that kept these accounts stable, expanding, and reference-ready.
The handover was incomplete — because there was nothing structural to hand over. No documented account plan. No relationship map. No escalation path. The VP’s knowledge was comprehensive, nuanced, and entirely personal. The CEO picks up the accounts but lacks the history. The customer contact says: ‘I’d like to discuss the expansion we were exploring with [VP name].’ The CEO does not know about the expansion. The conversation stalls while the CEO gets briefed on a deal that lived exclusively in the VP’s head.
One expansion opportunity — which the VP had been nurturing for 4 months and estimated at $45K incremental ACV — slows indefinitely. The context, the stakeholder relationships, and the commercial positioning all departed with the person.
Days 61–90: The CEO Is Running Revenue
The CEO’s weekly schedule now includes: running the revenue team (pipeline reviews, deal coaching, rep management), managing 3–5 key accounts personally, approving every discount and pricing decision, assembling the board pack, reviewing forecast deals individually, and interviewing VP Sales candidates in parallel. Total CEO hours on revenue functions: 30–35 per week.
Revenue may actually hold steady for one quarter — because the CEO is plugging every structural hole with personal bandwidth. The board sees a stable number and concludes the transition is being managed well. What they cannot see is the cost: the CEO has zero bandwidth for product strategy, fundraising, team development, customer strategy, or any strategic initiative that does not involve immediate revenue management.
The company survives the gap. The CEO does not have the capacity to lead through it and build the next stage simultaneously. The 90-day period is not a temporary inconvenience. It is a structural diagnosis — and the diagnosis is that the revenue system requires a specific person’s judgment, effort, and relationships to function. That is not a system. It is a dependency.
The Replacement Arrives
The new VP Sales starts in month 4 or 5, depending on recruiting timelines. They are experienced. They are capable. They have built revenue teams before. They ask for the playbook, the territory plan, the pipeline governance model, the pricing framework, the competitive positioning matrix, the account plans for key customers, and the historical win/loss analysis.
None of it exists. The new VP inherits the identical architecture their predecessor worked within: uncodified process, unstructured pipeline, ungoverned pricing, a CRM that tracks but does not manage, and zero documentation.
They apply different judgment to the same system. They have different strengths, different instincts, different management rhythms. But the architecture underneath them has not changed. The inputs are the same. The structural constraints are the same.
Six to twelve months later: the same structural revenue performance with a different name on the org chart. The board wonders what went wrong. The CEO is frustrated. The new VP, privately, knows: ‘I inherited a system without architecture. I’m managing with judgment — the same way the last person did. The system is the constraint. Not the people.’
The Structural Truth
The VP Sales departure did not create these gaps. It revealed them.
The forecast was always judgment-based. Pipeline hygiene was always person-dependent. Key accounts were always personally managed. Pricing authority was always centralised in one person’s discretion. The CRM was always a contact database rather than an operating system. Every one of these dependencies existed — masked by a competent VP’s daily effort — before the departure email was sent.
The VP’s competence was the architecture. Their judgment was the process. Their relationships were the account plans. Their discipline was the pipeline governance. The company did not have a revenue system with a VP Sales leading it. It had a VP Sales functioning as the revenue system.
And the replacement — no matter how talented, how experienced, how well-compensated — will inherit the same structural absence and produce the same structural result. Until the architecture underneath the role is built, every person in the role will reach the same ceiling.
Lead-to-Order Structural Assessment
Every pattern in this timeline is diagnosable before the departure happens. The Lead-to-Order Structural Assessment surfaces these dependencies proactively — including the Founder Dependency Map that shows exactly where the revenue process is person-dependent rather than system-governed.
See what the map reveals. The sample CEO was carrying 25–30 hours per week of revenue functions the process should govern. Most CEOs who read this article discover they are not far from that number. The question is whether you discover it now or when the next departure reveals it for you.
Before You Commit Capital, Credibility, or Momentum
Technology CEOs are increasingly using decision-grade GTM due diligence before high-stakes commercial bets — not to outsource judgement, but to ensure the decision stands up before it's made.
When a GTM decision is hard to unwind — a senior hire, a pricing change, a market entry — the cost of being wrong compounds quietly. Two quarters slip away before you know it failed.
Commercial Bet Due Diligence (CBDD) is a short, independent review used before commitment. It evaluates a single GTM bet across product, pricing, positioning, sales, and customer growth — and concludes with a clear verdict:
- Review a sample CBDD board memo — the artefact CEOs and boards use to govern these decisions
- Learn how the CBDD process works — and when it's applied
