Why Your Sales Team is Losing and You Don’t Even Know it
Most sales teams are broken, and the people running them have no clue. They drown in activity, chase bad deals, and celebrate pipeline volume like it’s a win, when in reality they’re bleeding revenue.
You don’t need a deep dive into spreadsheets or a consulting firm to tell you if your team is in trouble. There are three simple benchmarks that, if you’re missing, should stop you dead.
Win rates below 25% – you’re losing 75% of deals. That’s wasted time, wasted pipeline, wasted money.
Sales cycles dragging past industry norms – the longer a deal sits, the more likely it dies.
Average deal size shrinking or stagnant – if your deal sizes aren’t growing, your team is giving away margin or failing to sell the full solution.
Miss one of these? You’ve got a problem.
Miss all three? Your sales organization is fundamentally broken.
Fixing it doesn’t start with more tools, more enablement, or more pipeline. It starts with acknowledging the problem.
Win Rates Below 25%
If your win rate is below 25%, your sales team is a leaky bucket. You’re losing 3 out of every 4 deals that enter your pipeline. That’s unacceptable.
Think about what that means:
75% of reps time is wasted chasing deals that won’t close.
Marketing dollars vanish. You’re spending to generate pipeline that never converts.
Revenue is left on the table. The deals are there, but your team isn’t closing them.
The problem isn’t a lack of pipeline, the problem is that you’re losing on the opportunities you already have.
Why Your Team is Losing Deals
Your sales team is optimized. The deals in your pipeline should be winnable, but your reps are missing something.
Poor Qualification: Reps are chasing bad deals that were never going to close.
Weak Discovery: Reps don’t know the real problem so they can’t create value or urgency.
Product Pitching: They’re talking about features instead of diagnosing a problem.
How to Fix It
Ditch traditional Qualification methods: BANT and MEDDIC aren’t cutting it. If your team can’t articulate the buyer’s current state, future, state, and the gap between them they aren’t actually selling.
Dig into lost deals: If you don’t know why you lost, you’ll keep making the same mistakes.
Stop focusing on activity, start focusing on conversion: More calls, more demos, and more emails won’t solve this. Better execution will.
If you’re running a sales team with a win rate below 25%, you don’t have a pipeline problem, you have a selling problem. Fix that first.
Sales Cycles that Drag
Deals become less likely to close the longer they sit. Period.
Slow moving pipeline are deadly to sales organizations. They drain resources, destroy momentum, and fill forecasts with false hope. Your team is doing something wrong is your sales cycles stretch longer than necessary.
Healthy Sales Cycle Benchmarks:
- Deals under 100k close within 90 days
- Deals between 100k-500k close within 180 days
- Deals between 500k-1M close within 270 days
- Deals between 1M-3M close within a year
Miss these and your team is losing deals to inaction.
Why Deals Stall
Your team surrenders control: reps fail to create value or urgency, letting buyers dictate the timeline.
Discovery is weak: problems don’t feel urgent because the reps haven’t laid out the impacts of not fixing the problems now.
Reps targeting the wrong level: no executive sponsorship means endless back and forth with mid level managers.
How to Fix It
Identify the roadblock(s): what’s causing deals to stall? Lack of urgency? Too many stakeholders? Price objections?
Stop selling to people who can’t buy: If the team is stuck in an endless loop they’re probably talking to the wrong person. They must get the contact to agree to bring in the person with purchasing power.
Diagnose the buyer’s world: If your reps can’t tell you why waiting is costing the buyer money, the deal won’t close.
Long sales cycles kill win rates. Shorten them, and everything improves.
Flat or Shrinking Deal Sizes
If your average deal size hasn’t grown in the last 36 months, or it’s shrinking, there’s a problem. Your team is either discounting too much or failing to sell the full solution. Both are killing your revenue.
Why This is Happening
Reps are price cutting to win deals: Instead of defending value, they’re racing competitors to the bottom.
They aren’t selling the full scope of the solution: If reps are unable to expand a deal, they don’t understand the buyer’s full problem.
They’re missing cross or upsell opportunities: Reps aren’t identifying additional needs or positioning the right add-ons.
Impact of Shrinking Deal Sizes
Lower margins: Every discount slashes profitability.
Longer sales cycles: Smaller deals mean smaller impact, which means buyers feel less urgency and have a tendency to move slower.
Weak customer retention: Undersold customers churn because they never saw the full value.
How to Fix It
Train reps to sell on impact, not price: If they can’t defend the full value of the solution, they default to discounts.
Make deal expansion a priority: Reps should be uncovering problems that require bigger solutions, not just the easiest entry point.
Analyze deal trends: If your team’s pricing strategy is inconsistent, or deal size is shrinking in key segments, you need to know why.
Your team should be closing bigger deals over time, not smaller ones. If deal sizes aren’t growing, your sales process is working against you.
If You’re Missing These Benchmarks, Your Sales Team is Broken
It’s not complicated. If your team isn’t hitting these three benchmarks, you have a fundamental sales problem. Not a pipeline problem, not a marketing problem, a sales execution problem.
Win rates below 25%? Your team isn’t qualifying, discovering, or selling effectively.
Sales cycles too long? Your team isn’t creating urgency or selling to decision makers.
Deal sizes shrinking? Your team is discounting and failing to sell the full solution.
What To Do Next
Stop ignoring the numbers: These benchmarks don’t lie. If you’re underperforming, own it.
Diagnose the real issue: Is it weak discovery? Poor deal management? Discount addiction? Find the root cause.
Fix your sales process: Shift to a problem-centric approach, train reps to uncover real business problems, and reinforce deal execution.
Where Does Your Team Stand
You can’t fix what you don’t measure. If you don’t know you win rates, sales cycle length, or average deal size trends, you’re flying blind. If you do know them and they’re off, you’re running a broken sales team.
Your win rate tells you if your team can sell. Under 25%? They can’t.
Your sales cycle tells you if your team controls the deal. Too long? They don’t.
Your deal size tells you if your team sells on value or price. Shrinking? Price.
Dig In
Pull the data: Where do you actually stand against these benchmarks?
Identify the gaps: Why are you losing? Why are deals stalling? Why aren’t you maximizing deal size?
Fix it: Improve discovery, tighten deal management, and start selling on business impact, not just product.
Sales is measurable. Sales success is fixable. But only if you stop making excuses or looking for an easy button and start addressing the problems.
0 Comments