The board does not fire you for missing a quarter.
They fire you for missing two quarters and not being able to explain why. The first miss is weather. The second miss is architecture. And by the time the third miss arrives, the conversation has already moved from “how do we fix this” to “who do we bring in.”
Here is what makes this dangerous: the seven failures that actually kill a technology CEO’s tenure do not look like failures when they begin. They look like reasonable decisions. They look like growth. Some of them look like the board’s own advice.
Every pattern below is drawn from direct observation across 200+ GTM engagements with B2B technology companies between £3m and £100m revenue. None of these are theoretical. All of them have cost at least one CEO their job.
1. Pipeline Coverage That Looks Healthy Until It Isn’t
Most CEOs track pipeline coverage as a single ratio. Three-to-one. Four-to-one. The number looks adequate. The board sees it and moves on.
The failure is not in the ratio. It is in the composition.
When you decompose that 3x pipeline by stage, by source, by age, and by probability-weighted value, a different picture emerges. Seventy percent of the pipeline is early-stage. Forty percent was sourced by one channel that is already showing diminishing returns. A quarter of the dollar value has been sitting in the same stage for sixty days.
The ratio is 3x. The reality is 1.2x of pipeline that will actually close this quarter.
This is the most common revenue system failure in the $5M–$50M band because it is the easiest to miss. The dashboard says healthy. The system says otherwise. And the CEO who presents the dashboard number without understanding the system beneath it is the CEO who cannot explain the miss when it arrives.
The board does not distinguish between “did not know” and “did not check.” Both outcomes end the same way.
2. A VP Sales Hired Before the Sales Motion Is Validated
Every technology CEO hears the same advice at some point: “You need a VP Sales to take this to the next level.” The advice is not wrong. The timing usually is.
A VP Sales hired into a company where the founder is still closing the majority of deals, where the sales cycle is not documented, where the ICP is defined by instinct rather than data — that VP Sales will do exactly what they were hired to do. They will build a team, install a process, and run a motion.
The problem is they will run the wrong motion. Not because they are bad at their job. Because the right motion has not been discovered yet.
The detection signal is specific and measurable: win rate drops while pipeline grows. The new team is generating activity. They are not generating the right activity. And the founder, who has stepped back from selling to “focus on product and strategy,” no longer has the close-rate signal that would have caught the misalignment early.
Six months later, the board sees a team that costs £400K per quarter, a pipeline that has doubled, and a revenue number that has not moved. The CEO approved the hire. The CEO owns the outcome.
The correct sequence is the opposite of what most CEOs do. Before hiring a VP Sales, validate the sales motion yourself. Document the actual buying process. Identify the ICP from closed-won data, not from your pitch deck. Prove that someone other than the founder can close a deal using a repeatable process. Then hire the VP Sales to scale what works — not to discover what works.
The difference between these two approaches is typically twelve months and £600K in salary, commission, and opportunity cost. One produces a scalable sales organisation. The other produces an expensive lesson about timing.
3. Enterprise Repositioning Without a GTM Rebuild
Moving upmarket is the most seductive growth strategy in B2B technology. The deal sizes are larger. The logos are more impressive. The board loves the narrative.
The problem is that enterprise is not a bigger version of mid-market. It is a different system.
The buying process changes. The number of stakeholders multiplies. The sales cycle extends. The value narrative must shift from features to business outcomes. The proof requirements escalate from case studies to ROI models. The procurement process adds weeks or months to every deal.
Companies that attempt this transition by pointing their existing sales team at larger accounts — without rebuilding positioning, without restructuring the sales process, without retraining on enterprise buying psychology — experience a predictable sequence: longer cycles, lower conversion rates, team frustration, top-performer attrition, and eventually a revenue plateau that is worse than where they started, because the mid-market motion has been neglected while the enterprise motion has failed to materialise.
I have seen this pattern in more than thirty companies across SaaS, cybersecurity, and fintech. It resolves the same way in every case: either the CEO rebuilds the GTM from the ground up — which costs twelve to eighteen months — or the board replaces the CEO with someone who will.
4. Pricing Changed Without Positioning Changed
This one is quiet. It does not announce itself. It just erodes.
A technology company raises prices — often on advice from the board or a pricing consultant. The increase is justified by the product’s value. The new price is defensible in a spreadsheet.
But the sales team is still telling the old story. The website still positions the product the same way. The buyer hears a higher number attached to the same narrative, and the only rational response is to push back, delay, or ask for a discount.
Deal velocity slows. Discounting increases. The average selling price rises on paper but falls in practice. The CEO reports a “pricing adjustment” to the board. The board sees the revenue line and wonders why the adjustment is not flowing through.
The failure is not the pricing decision. It is the assumption that pricing exists independently of positioning. It does not. Price is the most visible expression of value. If you change the price without changing the value narrative — across sales, marketing, customer success, and the product experience itself — you create a gap that the buyer fills with scepticism.
5. Forecast Confidence That the CEO Cannot Verify
There is a version of this failure that is obvious: the CRO presents a forecast, the CEO presents it to the board, and the number misses. That version is painful but recoverable. The CEO adjusts the process and installs deal qualification criteria.
The dangerous version is subtler. The forecast is close enough. Within ten or fifteen percent. Quarterly. The CEO stops interrogating it because the pain is not acute. The board does not raise it because the variance is within tolerance.
But “within tolerance” quarter after quarter means the CEO has no idea whether revenue is predictable or lucky. They cannot distinguish between a system that produces reliable outcomes and a system that happens to be producing acceptable outcomes right now.
When the system breaks — and it will, because markets shift, champions leave, procurement policies change — the CEO has no diagnostic capability. They cannot identify what broke because they never understood what was working. They built their board confidence on a number that was approximately right, and now they have no mechanism to explain why it is wrong.
Forecast confidence is not about the forecast. It is about whether the CEO can decompose the revenue number into its constituent parts and explain the causal logic of each one. If they cannot do that on a Tuesday afternoon without scheduling a meeting, the forecast is theatre.
6. Retention Revenue Masking an Acquisition Collapse
Net revenue retention above 110% is the metric that makes everyone relax. The board sees it. The investors see it. The CEO reports it with confidence. Existing customers are expanding. The base is growing from within.
And beneath that number, new logo acquisition has quietly collapsed.
This failure is structurally invisible because NRR and new business operate on different timescales. A strong NRR today reflects decisions made twelve to eighteen months ago: good onboarding, strong product-market fit in the installed base, effective customer success. A weak acquisition engine today will not show up in the topline for another two to three quarters — by which time the NRR tailwind will have begun to fade as the denominator stops growing.
The CEO who reports strong NRR without simultaneously tracking and stress-testing acquisition health is the CEO who will present a beautiful board pack in Q1 and an unexplainable one in Q3.
7. Market Expansion Before Segment Mastery
The seventh failure is the one that boards most often encourage. “We should expand into Germany.” “The US market is ten times the size.” “Our product works for healthcare, too.”
Maybe. But the company that expands geographically or vertically before it has mastered its core segment — before the ICP is defined with precision, before the sales motion is repeatable, before the unit economics are proven — will spend eighteen months discovering that customer acquisition cost in the new market is three times the core market, that payback extends beyond viability, and that the management attention required to run two markets simultaneously has degraded performance in both.
Market expansion is not a growth strategy. It is a multiplication strategy. It multiplies whatever you already have. If you have a functioning, documented, repeatable revenue system, expansion multiplies revenue. If you have an undocumented system that works because of three talented individuals and favourable market conditions, expansion multiplies chaos.
The detection signal is always the same: CAC rises, payback extends, and the board starts asking why the new market “is not scaling as fast as expected.” It is scaling exactly as fast as the system supports. The system was never ready.
The hardest part of this failure is that the CEO often cannot reverse it cleanly. The new market has customers now — small ones, expensive ones, but customers nonetheless. Abandoning them feels like admitting failure. Continuing to serve them drains resources from the core. The CEO is stuck in the worst possible position: a market that is too small to justify and too established to exit.
The companies that expand successfully all share one characteristic: they expanded from a position of documented, repeatable, system-level mastery in their core market. They did not expand because they were bored, or because the board suggested it, or because a prospect in Germany asked for a demo. They expanded because the machine was built and the only question was where to point it.
The Pattern Beneath the Patterns
Every failure on this list shares one structural feature: it is invisible at the dashboard level and obvious at the system level.
Dashboards show outputs. Systems show architecture. The CEO who manages by dashboard will be surprised by every one of these failures. The CEO who understands the architecture of their revenue system — how leads convert to pipeline, how pipeline converts to revenue, how revenue retains and expands — will see them coming.
The CEOs who survive these are the ones who score themselves before the board does.
The Lead-to-Order Revenue Scorecard
Every pattern in this article is diagnosable. Most are identifiable in 48 hours.
The Lead-to-Order Revenue Scorecard is a scored, benchmarked assessment of your company’s complete revenue system — from lead generation through pipeline through conversion through retention and expansion. Six dimensions. Scored 1–5. Benchmarked against sector and stage-specific data. Annotated with operator-level observations from 25 years and 200+ GTM engagements across B2B technology companies at $5m–$100m revenue.
How it works:
30 minutes of your time. A structured call. 48-hour turnaround.
You receive a one-page scored assessment, benchmark comparisons, and a 15-minute recorded video walkthrough with specific observations about your revenue system — not generic advice, but what the numbers reveal about your company.
If your system is healthy, the Scorecard says so. You have independent confirmation for your board. If the system has a constraint, the Scorecard names where. You have clarity on what to investigate next.
$1,850 (£1,500). Single project. No multi-week engagement.
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
