5 Commercial Bets Tech CEOs Are Getting Wrong Right Now — And How to Spot Yours Before Q2
Published: December 2025 | Reading time: 8 minutes
Every quarter, we analyse commercial decision patterns across B2B technology companies — cybersecurity vendors, fintech platforms, SaaS businesses, and telecoms/IoT providers.
We track what’s working. We track what’s failing. And we track the gap between what CEOs believe is happening and what’s actually happening in their GTM motion.
Here’s what we’re seeing right now: the same five bets are failing across companies that otherwise look nothing alike.
Different verticals. Different stages. Different products. Same mistakes.
These aren’t strategy failures. They’re decision failures — bets made without enough diligence on whether the underlying assumptions were true.
If you’re a B2B tech CEO between £3m and £25m in revenue, at least one of these is probably in your Q1 plan.
This article will help you spot it before it costs you two quarters.
Bet #1: Hiring a VP of Growth (or VP Marketing) to "Fix the Funnel"
The pattern:
Pipeline is inconsistent. Conversion rates are slipping. The founder or CEO has been running GTM on instinct, and it’s no longer scaling.
The logical next step? Hire a senior marketing or growth leader to take ownership.
Why it’s failing:
In roughly 60% of the cases we’ve analysed this year, the VP Growth hire made within 6 months of identifying a “funnel problem” either churned within 12 months or failed to move the core metric they were hired to fix.
The issue isn’t the hire. It’s the sequencing.
Most companies hiring a VP Growth don’t actually have a growth problem. They have one of these:
- A positioning problem — the market doesn't understand why they're different
- A pricing problem — the economics don't support the sales motion
- An ICP problem — they're selling to everyone, converting no one
- A product-market fit problem — demand isn't there regardless of funnel
A VP Growth can optimise a working motion. They cannot create one. And when they’re hired to do the latter, they either fail or leave.
How to spot this in your business:
Ask yourself: If I gave this new hire a perfect team and unlimited budget, would they know exactly what to scale?
If the answer is “no” or “probably not,” you don’t have a growth leadership gap. You have a GTM clarity gap. Filling it with a hire is an expensive way to find that out.
What competitors are doing instead:
The companies winning right now are running GTM diligence before making the hire — pressure-testing whether their current motion can actually support a growth leader. Many are discovering that the right move is to hold, not hire.
📊 See how your competitors are structuring their GTM and sales motions:
Bet #2: Scaling Outbound Before Conversion Is Proven
The pattern:
Inbound is slow. Pipeline coverage is thin. The sales team is asking for more at-bats.
So you scale outbound: more SDRs, more sequences, more volume.
Why it’s failing:
Outbound is an amplifier, not a fixer.
If your conversion rate from first meeting to closed-won is below 15%, doubling outbound volume doesn’t double revenue — it doubles cost while revenue stays flat.
We’ve tracked multiple B2B tech companies this year that scaled outbound spend by 40–80%, saw meetings increase, and watched revenue stay static. In two cases, it actually declined (because sales attention was diluted across more low-quality opportunities).
The maths is unforgiving:
| Scenario | Meetings / Month | Conversion | Closed Deals | Revenue (£50k ACV) |
|---|---|---|---|---|
| Before | 20 | 12% | 2.4 | £120k |
| After (+80% outbound) | 36 | 10%* | 3.6 | £180k |
| Cost increase | — | — | — | +£15k / month |
Conversion typically drops when volume increases without motion improvement.
The net gain: £60k revenue for £180k in additional annual cost. That’s not scaling — that’s subsidising.
How to spot this in your business:
Look at your last 20 closed-won deals. What percentage came from outbound? What was the conversion rate from first meeting to close? What was the average sales cycle?
If outbound conversion is below 12% and sales cycles are lengthening, scaling is not the answer. Diagnosing why you’re not converting is.
What competitors are doing instead:
The sharper operators are holding outbound flat and investing in conversion infrastructure — better qualification, sharper positioning, tighter ICP targeting. They’re getting more revenue from the same volume, not more volume with the same (or worse) economics.
Bet #3: Repositioning Without Validating Buyer Perception First
The pattern:
The team is tired of the current positioning. Competitors have moved. The market has shifted. The board is asking about differentiation.
Time to reposition.
Why it’s failing:
Most repositioning efforts fail not because the new positioning is wrong, but because the old positioning was never understood correctly.
Here’s what we mean: companies assume buyers see them the way they describe themselves. They don’t.
When we run buyer perception audits, we consistently find a 40–60% gap between how a company positions itself and how buyers actually describe it. That gap exists before any repositioning.
So what happens? The company repositions away from a position buyers never held in the first place — and moves toward a position that may be equally misunderstood.
Six months later, pipeline is still soft, and now the team is confused about what they even stand for.
How to spot this in your business:
Run this test: Ask five customers (not prospects — customers) to describe what you do and why they bought. Record their exact words.
Then compare to your website headline.
If there’s meaningful overlap, your positioning is landing. If there’s a gap, the problem isn’t your positioning — it’s your delivery of that positioning across sales, marketing, and product.
Repositioning won’t fix a delivery problem. It will just give you a new message to deliver badly.
What competitors are doing instead:
Before repositioning, leading companies are running competitive positioning analysis — understanding how they are perceived relative to alternatives. That intelligence shapes whether repositioning is needed, and if so, where the gap actually is.
🎯 Understand how competitors are positioning and where the gaps are:
Bet #4: Shifting ICP (Mid-Market to Enterprise, or Vice Versa) Without Motion Clarity
The pattern:
Mid-market deals are taking too long. Or enterprise is too slow. Or SMB doesn’t have budget.
The answer? Move up-market. Or down-market. Change the ICP.
Why it’s failing:
Every ICP shift is a motion shift. And most companies underestimate what that means.
Moving from mid-market to enterprise isn’t just “bigger deals.” It’s:
- Longer sales cycles (9–18 months vs 3–6)
- Procurement and legal involvement
- Multi-threaded stakeholder management
- Reference and proof requirements that don't exist yet
- Different buyer personas with different language
- A completely different competitive set
We’ve tracked four SaaS companies this year that announced an “enterprise push” in Q1 and quietly walked it back by Q3. The sales team wasn’t structured for it. The content didn’t exist. The proof points weren’t there. And the pipeline that did emerge took twice as long to close at half the expected value.
The same is true in reverse. Moving down-market means lower ACVs, higher volume requirements, self-serve expectations, and marketing-led acquisition that most enterprise-focused teams aren’t built for.
How to spot this in your business:
Before committing to an ICP shift, answer this:
- Do we have any closed-won customers in the new segment?
- What was their sales cycle, ACV, and acquisition cost?
- Do we have references and case studies that speak to this segment?
- Is our current team capable of running this motion, or does it require new hires?
If the answer to #1 is “no,” you’re not shifting ICP — you’re starting from scratch. That’s a different bet, with different risk, requiring different diligence.
What competitors are doing instead:
The companies executing ICP shifts successfully are doing two things first:
- Running 5–10 test deals in the new segment before committing budget
- Analysing how competitors are winning in that segment — pricing, positioning, and sales motion
The second part is critical. If you’re entering a new segment, you’re entering someone else’s home turf. You need to know how they play before you step on the field.
Bet #5: Increasing Discounting to "Win More Deals"
The pattern:
Win rates are down. Deals are stalling. Competitors are aggressive.
The pressure response? Discount earlier, deeper, faster.
Why it’s failing:
Discounting doesn’t fix a value perception problem. It confirms it.
Here’s what the data shows: companies that increased discounting by more than 10 percentage points over 12 months saw no improvement in win rate, but a 15–25% decline in average deal value.
The deals they won, they would have won anyway — just at lower margin. The deals they lost, they lost for reasons discounting couldn’t address: poor fit, weak differentiation, or competitive positioning gaps.
Worse, aggressive discounting trains your buyers to wait. It trains your sales team to lead with price. And it trains your competitors to match, triggering a race to the bottom that no one wins.
How to spot this in your business:
Look at your discounting trend over the last 4 quarters. Then look at win rate over the same period.
If discounting is up and win rate is flat (or down), discounting isn’t solving the problem. It’s masking it — and destroying margin in the process.
What competitors are doing instead:
The companies holding margin are investing in competitive intelligence — understanding exactly how competitors price, bundle, and structure proposals. With that visibility, they can defend value without racing to the bottom.
They’re also training their sales teams on competitive objection handling — not “how to discount less,” but “how to position so discounting isn’t required.”
💼 See actual competitor pricing frameworks and bundling strategies:
How to Spot Your Commercial Bet Before It Fails
These five bets share a common thread: they feel like forward motion, but they’re often reactions to symptoms, not root causes.
- The CEO who hires a VP Growth to "fix the funnel" is reacting to pipeline inconsistency — but the cause might be positioning, pricing, or ICP.
- The CEO who scales outbound is reacting to pipeline coverage — but the cause might be conversion physics.
- The CEO who repositions is reacting to competitive pressure — but the cause might be message delivery, not message content.
The cost of guessing wrong isn’t just money. It’s time, credibility, and momentum.
A bad VP hire burns 6–12 months. A failed repositioning confuses the team and the market. A misguided ICP shift distracts the entire GTM org from the motion that was actually working.
Before You Commit to Your Next Commercial Bet
If you’re about to make one of these bets — or one like them — you have two options:
Option 1: Guess and learn.
Make the bet. See what happens. Course-correct if it fails. This works — but it’s slow and expensive, and you may not have the runway for trial-and-error.
Option 2: Get intelligence first.
Understand how competitors are actually pricing, positioning, and winning deals. See what’s working in your market before you commit budget, headcount, or credibility to a bet you can’t easily unwind.
That’s what the Competitive Deal Playbook provides:
- Real pricing frameworks, not guesswork
- Bundling and packaging tactics across your vertical
- Sales motion and GTM positioning intelligence
- Analyst-validated, updated monthly
It’s the diligence layer most companies skip — and the reason the five bets above keep failing.
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