I’ve spent more than 20 years working as a fractional CRO and CEO across startups, scale-ups and large tech businesses including HP and Microsoft. Much of that time has been spent diagnosing stalled pipelines, and I’ve seen faulty prospect targeting come up again and again as the thing that stalls them.
According to Forrester’s 2024 State of Business Buying Report, 86% of B2B purchases stall at some point during the buying process. And a consistent reason for this is getting your B2B buyer personas wrong. With this in mind it’s worth asking yourself whether you might actually be prospecting the wrong person.
The Foundation: Tight ICPs and Problem-Focused Value Propositions
When I first look at a stalled pipeline I ask two simple questions:
- Is it clear what problem the business solves?
- It is clear who actually has that problem?
Many B2B websites fail to answer these questions clearly or quickly enough. If a buyer has to spend time figuring out what you do because it’s not obvious, they won’t hang around for long. The problem you solve has to be front and centre, and it needs to be framed in the buyer’s language, rather than implied by your list of features.
This level of clarity is essential for ICP definitions too. Something like ‘mid-market and enterprise companies across Europe’ is a vague aspiration, not an ICP. You need something more specific so you can create a viable call list. Your ICP needs to include company size, operating country, decision-maker seniority, and the specific pain point your product satisfies. The more detailed your ICP, the better the value proposition will speak to your prospects.
The End-User Trap: Why Pitching the Coalface Causes Deal Stagnation
Operational workers are easy to engage. In tech, for instance, workers live with error-prone workflows so are genuinely interested in a solution. They may take your call, attend a demo and give you positive feedback, but they can’t actually buy anything.
The best they can do is advocate for you and flag your solution upwards. So what looks like momentum at the user level often stalls when they pass your solution on to the person who actually signs contracts.
End Users vs P&L Owners: Mapping the B2B Buyer Persona Divide
Diagnosing why deals stall is about recognising the gap between end users and P&L owners. Here’s how to distinguish between them:
| End-User Persona (Coalface Worker) | P&L Holder Persona (Executive / Budget Owner) | |
| Focus | Eliminating daily manual friction | Measurable ROI, cost reduction, revenue growth |
| Pain Point | Manual data entry, spreadsheets, paper-based processes | Falling behind competitors, missing quarterly targets |
| Buying Authority | Can flag issues upward; cannot authorise spending | Holds P&L responsibility, signs purchase contracts |
| Operating Timeframe | Immediate workflow convenience | Quarterly ROI cycles or long-term strategic initiatives |
Flipping the Script: Real-World Persona Realignment
I’ve seen bad targeting stall deals time and time again in various industries, but I’ve also been part of realigning that targeting.
In construction technology I saw outreach focused on the people closest to the operational problem. These were surveyors and project managers who engaged with the messaging, but couldn’t approve a purchase. By shifting targeting upwards to commercial directors and P&L owners, things improved significantly. These people cared about what the problem was costing the business, not how the software worked, and framing the outreach around this made a huge impact and led the business to win its first large enterprise account.
In retail technology a similar shift led to similar results. Initially solutions with multi-year sales cycles were being sold into complex venue environments with slow procurement processes. By refocusing towards heads of loyalty, CRM and customer experience – all operating on quarterly cycles and needing immediate in-store connectivity – the sales cycle was significantly reduced.
Cutting Through 2026 AI Noise: Warm Connections vs Scatter-Gun Outreach
Decision-makers today get dozens of automated sequences every day and tools like Apollo, ZoomInfo, Gemini, Claude and ChatGPT have made it easy to outreach at volume. But this also means this kind of outreach is very identifiable. Executive buyers are now experts at spotting and filtering out AI outreach.
I’ve seen a situation where AI outreach destroyed a lead where there was a great opportunity to make contact with a buyer. A contact received an automated sales email from a former school friend who had them in their prospecting sequence. When this contact replied in an appropriate human way to say hi, the AI response was a message discussing deliverability rates, completely ignoring the already existing relationship and ending any chance of a sale.
I remember a similar situation where the human approach – with no AI involvement – worked perfectly well. An SDR’s father had a connection to the Chairman and CEO of a business so the father made a call. The SDR then called the CEO’s secretary referencing the call. The secretary sent the follow-up email directly in front of the CEO and a high-level meeting was secured.
When I use AI myself it’s in a quite different way. Rather than sending out endless broad messages, I use Claude and Gemini to research prospects, crawling talks and interviews with target executives to pull quotes and find talking points that can be used in personalised LinkedIn outreach, and monitoring intent signals that indicate when a prospect is in-market. This approach leads to outreach that is appropriate for each target and has the best chance of engaging them.
But even when your targeting and personalisation are spot on, persistence matters. In fact, it can take up to 17 touchpoints across email, phone, LinkedIn and partner channels before you get a response from the right person.
Selling Through Economic Uncertainty: Must-Haves vs Nice-to-Haves
I’ve navigated numerous recessions yet I’ve never missed target just because of an economic downturn. It’s the press coverage of recessions, rather than the recessions themselves, that stall sales.
And the way to progress in times such as these is to make sure your offering isn’t seen as an enhancement or convenience. Instead, solutions need to show that they demonstrate fast return on a clear financial metric such as cost reduction or revenue protection. Plus some solutions sell if they’re essential for regulatory compliance.
How to Qualify Whether You’re Speaking to the Right Person
On a discovery call I use four questions to quickly establish whether I’m speaking to someone who can actually move the deal forward:
- Is this an identified problem for your organisation? This establishes whether there’s urgency above the individual being spoken to.
- If you had a solution to this, how would that work for you? This reveals whether the prospect is thinking in terms of personal workflow improvement or business-level outcomes.
- Who holds the budget and who would sign this off? This is the most direct route to understanding where authority sits.
- Who else does this problem impact up the management chain? This identifies escalation paths and the names needed to build a multi-threaded approach.
How E360 Helps You Target the Right Personas for Faster Growth
E360 brings a fractional CRO lens to stalled pipelines. This objective perspective can often identify where the targeting of B2B buyer personas has gone wrong better than the internal teams who no longer see things clearly.
Fixing this requires rebuilding the ICP definitions around who holds the budget, realigning value propositions around the financial outcomes executives care about, and retargeting (personalised) outreach away from end users and towards leaders whose quarterly goals your product can impact.
If you’re struggling with stalled sales and you’d like to get things moving again, get in touch with our team today.
FAQs
Why do deals stall after positive meetings with end users?
End users understand the problem and may be enthusiastic about your offering, but they can’t approve sales. If there’s no direct route from them to a decision-maker a deal is likely to die.
How do warm introductions improve access to executive buyers?
No one likes cold outreach so an introduction from a mutual contact gives you a much better chance of securing a meeting with someone at the right level.
How do you reframe a value proposition during a downturn?
In this situation it’s best to focus on fast, quantifiable ROI or mandatory requirements. Framing your product as an enhancement or convenience often isn’t enough during a downturn.
Why does automated AI outreach fail at the executive level?
Because executives have become experts at spotting AI outreach a mile off. They either see it and filter it out, or in the worst case you could burn the prospect forever.
