The biggest sales challenges companies face today share one uncomfortable trait: almost none of them are effort problems. I’ve spent decades working with sales organizations across every major industry, and I can count on one hand the teams that failed because people weren’t working. Teams fail because the environment changed while their approach stayed the same.
Leaders who can correctly diagnose their sales challenges and deploy the right strategies and resources to resolve those obstacles, are the ones that lead their companies to revenue growth no matter what market conditions they face.
Our firm’s Sales Performance Research across more than 1000 sales leaders and professionals confirms it. The gaps that prevent elite sales performance are alignment and execution gaps, not motivation gaps.
The Four Biggest Sales Challenges
Four sales challenges show up more consistently any others in our work across industries: sales cycles that got longer and more complex, prospecting that can’t earn attention, the constant fight to keep and develop sales talent, and sales and marketing operating in silos. Here is what causes each one, and how the organizations that solve them actually do it.
Sales Challenge #1: Longer, More Complex Sales Cycles
Closing a deal has become a marathon. Buying decisions in B2B markets now run through committees, with procurement, finance, and technical stakeholders all weighing in, and today’s buyers arrive at the first conversation having already researched the options, read the reviews, and formed expectations. The salesperson who shows up with a pitch is answering questions the buyer stopped asking weeks ago.
The solution starts with mapping the buying journey rather than your selling process.
- Who actually influences this decision?
- What is each stakeholder trying to solve?
- What will stall the deal at each stage?
Salespeople who can answer those questions run multi-stakeholder deals with intent, and salespeople who can’t are single-threaded on one champion and hoping. The consultative skills underneath, structured discovery and diagnosis before recommendation, are exactly what separates teams that advance complex deals from teams that watch them stall.
Here’s the part most leaders miss: our research found that while 60% of salespeople say they understand their organization’s sales methodology, only 32% execute it consistently. In a complex sale, that inconsistency is fatal, because a nine-month deal touched by four salespeople selling four different ways is a deal the buyer experiences as chaos.
Sales Challenge #2: A Prospecting That Can’t Break Through the Noise
Your buyers are drowning in outreach. Emails, LinkedIn messages, cold calls, ads, most of it generic, all of it ignored. When prospecting stops working, the reflex is more volume, and more volume of the same generic message just trains the market to ignore you faster.
The fix is precision. Sharpen the ideal customer profile until your team can name the industries, company sizes, and roles where you actually win. Run a multi-channel cadence, phone, email, social, and video together, rather than betting everything on one. And personalize against the prospect’s business problem, because relevance is the only thing that has ever earned attention.
There’s a math layer here too, and it’s where the discipline shows. Fewer than half of the salespeople in our study could say how many deals they need to close to reach their sales goals, and even fewer knew how many opportunities they need to generate to get there. A team that doesn’t know its own math can’t prospect with discipline, because nobody knows what enough looks like. Define the inputs, and prospecting stops being an act of faith.
Sales Challenge #3: Retaining and Developing Sales Talent
Ask any sales leader their hardest problem and most will land here. Sales is a high-pressure profession, burnout is real, turnover disrupts pipelines, and replacing a productive salesperson costs far more than keeping one.
Hiring matters starts with onboarding, where our research found a telling gap: 51 percent of sales leaders rate their onboarding highly while only 34 percent of salespeople agree. The people going through the program experience something very different from what leadership believes it built, and slow, unstructured ramp is one of the quietest drivers of early turnover in sales.
Then comes development, and this is the retention lever leaders underuse. Salespeople stay where they’re getting better. That means training tied to real skill gaps rather than generic content, and it means managers who actually coach. In our data, salespeople rate their own skills far higher than their leaders rate them, with gaps of more than 30 points on core capabilities, and that gap persists wherever coaching is sporadic. Structured sales coaching closes it, and it does double duty: it improves performance and it tells your best people the organization is invested in them.
Sales Challenge #4: Sales and Marketing Working in Silos
The oldest challenge on this list is still one of the most expensive. Sales blames marketing for lead quality, marketing blames sales for follow-up, and the buyer experiences a disjointed journey while both teams hit their separate metrics.
Alignment starts with shared numbers. Hold both teams accountable to the same KPIs: lead quality, pipeline velocity, and revenue contribution, not activity counts that let each side declare victory independently. Build a standing feedback loop where sales reports what prospects are actually asking and marketing adjusts campaigns to match. For organizations selling into high-value accounts, account-based approaches force the collaboration structurally, with both teams building personalized campaigns against the same named targets.
And when you launch a shared sales methodology or sales process, put marketing in the room for the sales training. A marketing team fluent in how the sales organization sells produces content and leads that fit the motion instead of fighting it.
The Thread Running Through Every Sales Challenge
Look back across all four challenges and you’ll notice they share a root. Complex sales cycles punish teams without a consistent process. Prospecting fails without defined math and discipline. Talent leaves when development is an afterthought. Silos persist when nobody aligns the system. Every one of them is a system problem wearing a different costume, which is why solving them piecemeal produces improvement that doesn’t last.
That’s the thinking behind Sales Team Science®, our framework for diagnosing where sales performance actually breaks down across leadership, management, talent, process, methodology, and enablement, and building the fix around what the data reveals. Before you buy another tool or another training program, find out which of these challenges is actually costing you the most. The answer is almost never the one leadership assumes.
Solve the Sales Challenges Holding Your Team Back
Every sales challenge in this post is solvable, and the organizations that solve them share one habit: they diagnose before they prescribe.
Reach out today to see where your sales organization stands and which challenge to tackle first.
