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The Top Challenges Facing B2B Sales Leaders in 2026

The Top Challenges Facing B2B Sales Leaders in 2026

By Ian Hirst, Greenbank CEO

 

I think it’s fair to say that the B2B sales environment in 2026 is more volatile, complex, and uncertain than at any point in the last decade. Unprecedented geo-political turbulence, AI‑accelerated disruption and increasing (and more varied) competition have collided to create a uniquely difficult frontier for sales leaders, with risk-averse buyers often frozen into inactivity…

Although we work globally with clients in a diverse range of sectors from SaaS technology startups, global business consultancies and manufacturing companies, the challenges that they are facing are remarkably similar.

So, with 2026 already well underway – and on the basis that you might be facing some similar challenges, I thought the following summary of 3 of these challenges (and what to do about them!) might be helpful!

I wish you all the best in 2026

Ian Hirst

CEO Greenbank

1. Addressing sales team silos

 The challenge: 

Growth demands consistency, cohesion, and communication —and many commercial organisations today struggle to sustain this due to entrenched silos within their go-to-market function.

This is backed up by a recent LinkedIn report suggesting that ‘revenue engines’ entering 2026 are deeply fragmented, with the different key role in the sales process – typically Lead generators (SDRs) , Sales Execs (AEs)  and Customer Services/Account Managers (CS) often having different C-Level reporting lines, terminology, processes and supporting technology. 

Add in regional differences into the mix and the issue gets even more complex…

Our own experience:

We completely agree with this and  have found that teams can have diverse definitions of key terms like ‘Qualified Opportunity’ and even fundamentally different views on their companies’ competitive differentiators and value proposition.

It’s not always clear exactly what a team’s role is in the revenue process and how that fits into other teams in the cycle – so no surprise that ‘inconsistent handovers’ from lead generators to sales execs and then onto account managers is a common issue.

One other related factor we are now also finding is the increasing importance of Subject Matter Experts (typically product managers or content owners) in the sale process – largely driven by the increasing complexity of technology solutions – which of course brings another group into the cycle.

The business impact:

The knock-on effects of this are fairly widespread and we have seen…

  • An inconsistent buying process – with prospects seeing different messages from each group throughout the cycle
  • Confusion as to how teams and individuals are measured – and the behaviours that are expected from them.
  • Poor forecasting
  • Difficulty in scaling sales operations, restricting growth
  • Slower decision making

Our top tips:

So, what do we see top organisations doing?

Well, in addition to the obvious organisational reporting alignment (making the CSO/CRO ultimately responsible for each group), some of the other things we have seen work well include:

  • Define and communicate clear metrics for each group – not just the obvious ‘lagging’ measures such as sales numbers, but the key ‘leading indicators’ for each team which would signal that things are on track or not. Example here might be;
    • weighted pipeline as a % of target
    • # identified stakeholders per prospect
    • effective use of specific tools & process

Communicating the team’s performance against each metric via a clear dashboard keeps this transparent – and also acts as a management tool for prioritising a team’s monthly focus

Some clients have taken this to the next level and identified individual personal targets for each metric and even the key behaviours they are looking for.  We worked with one client on this recently and amazingly they found that simply communicating these league tables, motivated individuals to up their performance – especially in areas where they were behind their colleagues…

  • Articulate a consistent value proposition for each product or service for each group to use.  Reinforcing the key competitive differentiators their company has.
  • Clearly define terminology and handover processes: An obvious one maybe, but again one that is helped the sales leadership team is working effectively together under the guidance of a single C-level exec!

2. Buyers are more informed — but more paralyzed by risk

The challenge: 

Modern B2B buyers might show up earlier in the process with AI‑driven research — yet even with all this available data, sluggish growth and geo-political uncertainty means they are less confident than ever and LinkedIn describes 2026 as a year where risk aversion and subsequent buyer paralysis is greater than ever before.

Our own experience

From our own pre-workshop discovery interviews with sales teams over the last few months, it’s clear that one of the main barriers they are facing are buying teams convincing themselves that status quo choices and “no decision” decisions are smart moves. 

The business impact:

Longer sales cycles and over-optimistic sales forecasts, especially when salespeople don’t recognize the complexity of the buying process and the hoops their contact might need to go through..

Our top tips:

A key sales skill for 2026 is enabling confident buying — not just providing information.  For example:

  • Use ‘disciplined curiosity’ to understand each prospects specific pain points. From the very first sales call, rather than make assumptions, sellers need to ask challenging questions to help diagnose a prospects specific pain points and clarify root causes. Then take it to the next stage by quantifying the cost of inaction (for example knock-on risks to other functions, opportunity loss and competitive threats).
  • Create urgency for change throughout the whole buying team. Having identified these pain points, top sellers help their main contacts articulate this to the rest of the buying team – eg providing powerful emails or proposals for them to circulate to colleagues which clearly identify the costs and risks of doing nothing.
  • Remove the fear of messing up. Every buying decision has its risks, and confident sellers are not afraid to talk about this and show ways their proposal will mitigate against it.  Our top tip here is to proactively suggest success metrics for the project – providing confidence that you are thinking beyond the sale.

3. An exceptional buying experience is more important than ever

The challenge: 

We are all overwhelmed by  poor quality bulk emails and ‘vanilla’ AI-driven content throughout social media channels.   So, the last thing that buyers in 2026 need is a standardised non-personal selling approach when they actually want to buy something!

Given this – from the very first call, prospects need to see value – from the actual interactions  with the selling organisation as well as the potential solution you might offer.  

Our own experience

We are constantly surprised that organisations don’t put themselves in the shoes of their buyers and consider what the buying experience they offer is actually like – from initial outreach, through to first calls and then follow up.  Certainly, as buyers ourselves of business services, we rarely finish a call with a potential supplier and think “do you know I’ve really learned something from that!”. 

The good news is that with a relatively small investment in time and training, you can quickly make this a real differentiator.

The business impact:

Several studies (eg Challenger, Gartner) have shown that the quality of the buying experience is more important than technical differentiators in b2b decision making.    Similarly,  HubSpot’s analysis shows that up to 72% of lost deals stem from poor value demonstration, not product issues.    So, if you want to differentiate your offering from competitors, you may want to consider making developing  the way you sell at least equal priority to product development investment!

Our top tips:

Start by making the very first sales call a memorable experience – for example:

  1. Control without pressure – Great sellers lead the call gracefully.
  2. Buyer-centric, not pitch-centric -Discovery first. Pitch second.
  3. Insight-rich – Buyers should feel that the call was valuable—even if they never buy.
  4. Crisp pacing – Each section has a purpose; nothing drags.
  5. Emotional rapport + intellectual credibility – People buy from those they trust and respect.

Then make sure that every follow up email, proposal and pitch is equally buyer-focused – providing valuable insights about their market, recent trends etc.

A good test here is to look at the content and follow the 70:30 rule – 70% of the content should be buyer focused (reflecting your deep understand of their pain points, educating them about latest trends etc) with only 30% focused on your offering and organisation.

And finally…

Greenbank are an innovative global training consultancy, working with b2b sales professionals on interesting, latest techniques which are 100% relevant to today’s business world we live in.  So, whether you are selling SaaS solutions, complex consultancy, new whizz-bang ideas or indeed anything that requires you to articulate the tangible value of what you do, we can probably help you.

Give me a call if you would like a relaxed, informal conversation and we can share ideas!

About Greenbank

Greenbank are an innovative, ‘boutique’ consultancy delivering completely tailored leadership, negotiation and sales development programmes to clients ranging from top 5 global firms to tech start-ups.

We are now delighted to be running truly blended programmes, which make the most of both virtual platforms and interactive face-to-face workshops, to deliver motivational, cost-effective development.

We also have our own industry-leading, multi-lingual, 360° assessment platform, Navigator360 which provides our clients and other training providers with a completely flexible approach to gathering powerful confidential feedback.

If you would like to discuss how we can help your own sales or leadership teams, then we would be delighted to have a relaxed conversation – please contact Ian Hirst or (+44) 7812 074359.