Looks like leadership. Usually becomes a two-quarter bonfire.
If you’re the CEO of a $5–$50m B2B technology company, 2026 will force you to make decisions that look obvious.
Hire the senior leader.
Move upmarket.
Scale outbound.
Fix pricing.
“Act decisively.”
Here’s the uncomfortable truth:
Most of these moves are not strategies.
They’re bets.
And the problem with bets at your stage isn’t ambition — it’s irreversibility. One wrong commitment can burn two quarters of cash, credibility, and momentum before you’re even able to unwind it.
What follows are seven GTM decisions that signal confidence to boards and teams — but quietly kill companies at your stage when made without diligence.
If you’re about to do one of these, the question isn’t whether — it’s which.
1. Hiring a VP Sales to “Fix Pipeline”
This is the most common expensive mistake in B2B tech.
Pipeline feels soft. Forecasts slip. Board pressure rises.
So you hire a VP Sales.
The assumption:
“An experienced leader will fix execution.”
The reality:
Sales leadership amplifies what already exists.
If your offer, ICP, messaging, pricing, and proof aren’t locked, a VP Sales doesn’t fix the problem — they scale the confusion. They introduce process, targets, and headcount on top of an unvalidated motion.
Six months later:
- Pipeline volume is up
- Conversion is flat
- CAC explodes
- The VP asks for more headcount
The company concludes: “Sales is hard.”
It wasn’t.
The decision was premature.
2. Repositioning for Enterprise Without Proof of Willingness to Pay
Enterprise repositioning is seductive.
Bigger deals.
Longer contracts.
Board-friendly narrative.
But most $5–$50m companies mistake interest for commitment.
Enterprise buyers will:
- Take meetings
- Ask questions
- Run pilots
That is not demand.
Real proof looks like:
- Budget ownership clarity
- Buying committee alignment
- Security and compliance acceptance
- Commercial terms that survive procurement
Without this, “enterprise GTM” becomes:
- Slower cycles
- Higher cost of sale
- Internal product sprawl
- Starved core customers
You don’t move upmarket.
You drift into strategic ambiguity.
3. Scaling Outbound Before Conversion Physics Work
When growth slows, volume feels like action.
More SDRs.
More sequences.
More tools.
More activity.
But outbound only works when conversion physics are proven:
- ICP precision
- Message-market resonance
- Sales handoff clarity
- Close path repeatability
Scaling volume before these are stable doesn’t create growth.
It magnifies inefficiency.
What you get:
- Burnt leads
- Demoralised SDRs
- Misleading pipeline metrics
- A false sense of momentum
Volume is not leverage.
It’s a multiplier — for better or worse.
4. Adding a Second Product Line (“Platform” as a Coping Mechanism)
This usually starts with a reasonable sentence:
“Customers are asking for…”
But what customers ask for is not always what scales.
Second products at your stage introduce:
- Diluted positioning
- Fragmented roadmap
- Complex sales conversations
- Support and CS strain
Worse, they often hide a harder truth:
The core product isn’t yet sharp enough to dominate its lane.
“Platform” becomes a narrative solution to a GTM problem.
Markets reward clarity, not breadth.
5. Changing Pricing Without Isolating the Real Constraint
Pricing is the most powerful lever in your business — and the most dangerous when misused.
When deals stall, pricing gets blamed.
But price is rarely the first failure point.
More often, the constraint is:
- Value articulation
- Proof of ROI
- Buying committee alignment
- Risk perception
Lowering or reshaping pricing without isolating the issue:
- Attracts the wrong buyers
- Damages perceived value
- Compresses margins permanently
Pricing changes should follow evidence, not frustration.
6. Buying Tools to Solve a Broken Motion
IMAGE PLACEMENT: Section image
(Concept: stacked tools covering structural cracks)
CRM upgrades.
Intent data.
AI SDRs.
RevOps platforms.
Tools feel safe because they’re reversible.
But tools don’t fix:
- Unclear ICPs
- Weak value propositions
- Broken handoffs
- Misaligned incentives
They create the illusion of progress while embedding dysfunction deeper into the system.
If your motion doesn’t work manually, automation won’t save it.
7. “We’ll Figure It Out as We Go”
This sounds flexible.
It’s usually avoidance.
What’s missing:
- Clear success criteria
- Kill thresholds
- Time-to-signal expectations
- Explicit downside protection
Without guardrails, every decision becomes emotional.
Momentum replaces measurement.
By the time reality asserts itself, the cost is already sunk.
The Grown-Up Move in 2026: Diligence, Not Bravado
Here’s what disciplined CEOs are doing differently in 2026:
They treat GTM decisions like investments.
Not opinions.
Not debates.
Not gut calls.
One decision.
Pressure-tested across:
- Product
- Positioning
- Pricing
- Sales
- Customer Success
With explicit answers to:
- What must be true
- Where risk concentrates
- When signal appears
- What gets stopped if it fails
Sometimes the right answer is GO.
Often, it’s HOLD — and preserve capital.
Occasionally, it’s STOP — before two quarters disappear.
That’s not hesitation.
That’s leadership.
Make One Decision Defensible
If you’re facing a high-stakes GTM decision right now — hire, reposition, pricing, outbound, expansion — the worst option is drifting forward without clarity.
The GTM Verdict applies due diligence discipline to one commercial decision in 14 days, delivering a board-ready answer:
GO / HOLD / STOP
👉 Book a GTM Verdict Call:
https://techgrowthinsights.com/gtm-growth-leader/commercial-bet-due-diligence/
One decision.
Fourteen days.
No theatre.
No regret.
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
