Day 1 feels manageable. The pipeline is full. The team knows their accounts. The forecast was submitted last week.
By Day 45, three of those statements will be false. By Day 90, the board will be asking questions you thought you had another quarter to answer.
This timeline is not pessimistic. It is a pattern. Across dozens of leadership transitions in B2B technology companies at the $5M–$50M mark, the sequence below repeats with remarkable consistency. The specific deals change. The specific people change. The structural breakdown does not.
The reason is not that VP Sales departures are inherently destructive. It is that the departing leader was carrying system dependencies that were never documented, never transferred, and never stress-tested. The departure does not create the vulnerabilities. It reveals them.
Days 1–10: The Forecast Becomes Fiction
The forecast submitted before the departure was the VP Sales’ forecast. It reflected their judgment about deal probability, their relationships with key champions, their read on timing, and their implicit knowledge of which deals were real and which were in the pipeline for optics.
Without that judgment layer, the forecast is a spreadsheet. The numbers are the same. The confidence is gone.
Within the first ten days, the CEO or acting leader reviews the pipeline and discovers that several “commit” deals depended on relationships the VP Sales owned personally. One or two deals were in the pipeline primarily because the VP Sales had committed them to the board and was going to force them through. The stage criteria that looked rigorous were, in practice, the VP Sales’ subjective assessment.
What the CEO will feel: the first tremor. Not panic — the pipeline still looks full — but a growing awareness that the numbers on the screen may not mean what they meant last week.
Days 10–20: The Team Starts Hedging
The sales team is professional. They will not immediately look for new jobs. But they are watching. They are reading signals. And the primary signal they are reading is: does the CEO know how to run a sales organisation?
If the answer appears to be no — and in many $5M–$50M companies, the CEO has not directly managed the sales function in years — the team begins to hedge. Top performers start having quiet conversations with recruiters. Mid-performers reduce their activity, waiting for clarity before committing effort to a number they are not sure will be fairly measured. Junior reps, who depended on the VP Sales for coaching and deal support, begin to stall.
The activity metrics will not reflect this immediately. CRM data entry continues. Meetings are held. But the quality of execution — the call preparation, the follow-through, the strategic deal management — degrades in ways that are invisible in the dashboard and obvious in the win rate four to six weeks later.
What the CEO will feel: a sense that everyone is being professional and cooperative, but that the energy has shifted. Meetings that used to be decisive become informational. The team asks more questions and takes fewer risks. This is not defiance. It is rational self-preservation. The team is waiting for a signal that the CEO understands their world — and most CEOs at this stage cannot send that signal because they have been operating at a different altitude for years.
The mistake most CEOs make in this window is trying to be the VP Sales. They attend pipeline reviews. They join customer calls. They offer tactical advice on deals. None of this is harmful, but none of it replaces the sustained, daily, granular engagement that a dedicated sales leader provides. The team knows the difference between a CEO who is temporarily covering and a CEO who understands the job. They respond accordingly.
Days 20–35: Deal Qualification Collapses
The VP Sales was the deal qualification authority. They decided which opportunities were real, which needed more work, and which should be disqualified. This was not a formal process — it was a weekly pipeline review where the VP Sales’ pattern recognition did the work that a documented qualification framework should have done.
Without that authority, deals that should be disqualified remain in the pipeline. Reps who should be redirected continue working unqualified opportunities because nobody has the credibility or the expertise to tell them otherwise. The pipeline swells with low-probability deals that feel like activity and produce no revenue.
Simultaneously, deals that needed the VP Sales’ intervention to advance — the enterprise opportunities where the VP Sales had executive relationships, the competitive situations where the VP Sales’ experience guided strategy — begin to stall. They do not immediately die. They enter a holding pattern. The prospect stops responding to the AE and waits for “the new person.”
Days 35–50: The CRM Becomes Unreliable
Every CRM reflects the discipline of the person who enforced it. The VP Sales required stage updates after every customer interaction. They required close-date accuracy within two weeks. They required loss reasons on every closed-lost deal. These requirements were not in a policy document. They were enforced through weekly reviews and direct feedback.
Without that enforcement, CRM hygiene degrades within weeks. Stage updates lag. Close dates are pushed without explanation. Notes become sparse. The CRM, which was a reasonably accurate reflection of pipeline reality, becomes a historical record of where deals were when someone last bothered to update them.
The CEO, who relies on CRM data for board reporting and internal planning, is now making decisions based on information that is increasingly stale. The gap between the CRM view and the actual pipeline widens daily.
This is the window where the CEO must decide whether to enforce CRM discipline themselves — which is possible but time-consuming and politically complex — or accept that the data will be unreliable until new sales leadership is installed. Most CEOs choose a third option: they assume the CRM is “roughly right” and continue to report from it. That assumption becomes the foundation of the forecast miss that arrives in the next phase.
The structural lesson is that CRM hygiene is not a technology problem. It is a leadership problem. The CRM was accurate not because the software was good, but because a specific person enforced specific standards through consistent, direct feedback. Remove that person, and the standards evaporate within weeks. The CEO who wants a reliable CRM after a leadership departure must either provide that enforcement themselves or accept a three-to-six-month gap in data quality.
Days 50–60: The First Forecast Miss Arrives
This is the moment the board notices. The forecast submitted at the beginning of the month, based on the degraded CRM data and the unqualified pipeline, misses. Not catastrophically — perhaps 15% below target — but enough to require an explanation.
The CEO’s explanation will reference the VP Sales departure. The board will accept this once. They will not accept it twice. The clock is now running on the CEO’s credibility.
What makes this moment particularly dangerous is that the CEO cannot yet distinguish between a temporary disruption (deals delayed because of the transition) and a structural problem (the revenue system was dependent on the VP Sales in ways that a replacement cannot easily replicate). The CEO wants to believe it is temporary. The board wants to believe it is temporary. The data cannot yet confirm either way.
The experienced board member is not looking at the size of the miss. They are looking at the CEO’s diagnostic quality. Can the CEO decompose the miss into its component causes? Can they identify which deals slipped, which were lost, and which were never real? Can they distinguish between pipeline problems, conversion problems, and timing problems? If the CEO can do that, the miss is manageable. If the CEO offers a narrative — “the team is adjusting to the transition” — without data, the board begins to lose confidence not in the sales team, but in the CEO.
Days 60–75: Top Performer Attrition Begins
The top performers have been watching for sixty days. They have seen the forecast miss. They have experienced the absence of coaching and deal support. They have drawn their own conclusions about the CEO’s sales fluency and the company’s ability to hire a replacement quickly.
The first resignation letter arrives. It is always the top performer. It is always the person the CEO assumed was safe. And it is always accompanied by the phrase: “I have been thinking about this for a while.”
This phrase is important. It means the decision was not made on Day 60. It was made on Day 20 or Day 30, when the top performer first concluded that the transition would be poorly managed. They have been interviewing for weeks. They have an offer. The resignation is the final step, not the first.
The impact is immediate and multiplicative. The departing rep takes their pipeline — not contractually, but practically. The deals they were working will not survive the transition to another rep. Prospects who had a relationship with that rep will pause, re-evaluate, and in many cases go dark. The remaining team sees the departure as confirmation of their own concerns. The second-best performer starts returning recruiter calls. The recruiting timeline for a VP Sales replacement, which was already under pressure, now includes an additional AE hire.
The financial cost of a single top-performer departure at this stage is typically three to four quarters of their quota contribution — the combination of lost pipeline, delayed deals, recruiting costs, ramp time for the replacement, and the productivity impact on the remaining team. At $5M–$50M revenue, that is $500K to $1.5M in revenue impact from a single resignation.
Days 75–85: The Compensation and Quota Questions Surface
Without a VP Sales to manage compensation disputes, quota adjustments, and territory conflicts, these issues — which were previously handled one-on-one, informally, and with political skill — now land on the CEO’s desk.
The team wants to know: will quotas be adjusted to reflect the pipeline disruption? Will compensation plans be restructured? Will territories be redrawn now that a top performer has left?
These are reasonable questions. They are also questions the CEO is poorly equipped to answer without sales leadership in place. Every answer the CEO gives will set a precedent that the incoming VP Sales may need to reverse. And every day without answers erodes the team’s confidence that the company has a plan.
The compensation question is particularly toxic when left unresolved. If a rep’s quota was set assuming pipeline support from the VP Sales, and that support has evaporated, the rep has a legitimate grievance. They are being held to a number that was achievable under conditions that no longer exist. The CEO who ignores this will lose more reps. The CEO who reduces quotas unilaterally undermines the incoming leader’s authority. The CEO who promises “we will make it right” without specifics creates an expectation that may be impossible to meet.
The correct response is bounded and honest: acknowledge the disruption, commit to a formal review within thirty days of the new leader’s start date, and offer a short-term adjustment mechanism — reduced accelerator thresholds, a transition bonus, or a guaranteed minimum — that protects the team without permanently changing the compensation structure. Few CEOs at this stage have the sales compensation expertise to design this independently, which is itself a system dependency that the departure has exposed.
Days 85–90: The Board Conversation Changes
By Day 90, the board has seen one forecast miss, one top-performer departure, and a CEO who has been spending 40% of their time managing a sales team they were not supposed to be managing. The conversation in the board meeting has shifted.
It is no longer: “When will we hire a replacement?”
It is: “Do we understand what was actually happening in the revenue system, and can we fix it before we hire someone new?”
This is the right question. But it is ninety days late. The CEO who commissions a system diagnostic at Day 90 will spend thirty to sixty days understanding what broke. The CEO who commissioned one at Day 1 would have had that understanding before the first forecast miss, before the first resignation, and before the board conversation changed.
The difference is not intelligence. It is not foresight. It is whether the CEO treated the departure as a hiring problem or a system problem. Hiring problems have a linear solution: find someone, hire them, wait for them to ramp. System problems have a diagnostic solution: understand what the departing leader was actually doing — not their title, not their responsibilities, but the specific system functions they performed — and determine which of those functions can be distributed, which must be replaced, and which were never sustainable as single-person dependencies.
The CEO who answers those questions before hiring is the CEO who hires the right person. The CEO who hires first and discovers the system later will repeat the cycle.
The System Truth
Every item on this timeline is a system dependency that was never documented, never transferred, and never stress-tested.
The VP Sales’ forecast judgment. Their deal qualification authority. Their CRM enforcement. Their coaching function. Their relationship capital with key accounts. Their political skill with the team. These are not leadership qualities — they are system functions that happened to reside in a single person.
The departure did not create these vulnerabilities. It revealed them. The only question is whether you map them now or discover them in the board pack.
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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
