Your Enterprise Sales Team is Bleeding Money -Here's How to Stop It
Five Warning Signs Your Sales Team is Failing -And Your Competition Knows It
Have a sneaking suspicion your enterprise software sales team is leaving millions on the table?
I’ve spent 20 years working with tech companies, and here’s the shocking truth: Most leaders realize their sales team is struggling but ignore doing anything about it until it’s too late.
Let me share something that might keep you up tonight: The average enterprise software deal takes 6-9 months to close.
But here’s what most CEOs don’t know: 40% of that time is wasted on deals that were never going to close.
Let's talk about what's really happening in your sales team (and how to fix it).
Here are the five warning signs your enterprise sales team needs immediate attention:
1. Your sales cycle keeps getting longer. When deals drag on, it’s not just lost time. Each extra month in your sales cycle is costing you 8.3% of your annual revenue potential.
Want to know something scary? A healthy enterprise sales cycle is 180 days. If yours is hitting 240 days, you’re burning $1M per rep in opportunity cost.
2. Your POCs aren’t converting. Proof of concepts should convert at 70%+. Anything less means you’re investing resources into dead-end opportunities.
3. Deal sizes are shrinking. Enterprise deals should grow year over year. If your average deal size is declining, your team is likely:
- Discounting too heavily
- Missing upsell opportunities
- Failing to reach true decision-makers
4. Your pipeline is full of “zombie deals.” These are opportunities that never die… but never close either. They’re worse than a straight “no” because they drain your team’s energy, expend resources, and cloud your forecasting.
5. Win rates against competitors are declining. This is the canary in the coal mine. If you’re losing more competitive deals than last year, your product is becoming less competitive or your sales team has lost its edge.
But here’s the good news: You can turn this around in 90 days.
Let me share what I’ve seen work with dozens of enterprise software companies.
How to Diagnose and Fix the Problem
If you suspect your sales team isn’t where it should be, here’s what you can do:
Audit Your Sales Process
Are reps following a structured sales process?
Are tools like CRM being used effectively?
Analyze Key Metrics
Look at conversion rates, average deal size, and sales cycle length.
Identify where deals are stalling.
Evaluate Your Talent
Are the right people in the right roles?
Do they have the necessary training and resources?
Improve Enablement
Provide targeted coaching and continuous learning.
Equip your team with better product knowledge and competitive insights.
Align with Marketing
Ensure a clear handoff between marketing and sales.
Collaborate on messaging to create stronger demand.
Refine Your Compensation Plan
Does your comp structure incentivize the right behaviors?
Align incentives with long-term growth goals.
Seek External Expertise
Sometimes an outside perspective can highlight blind spots.
Consider working with a software sales recruitment agency to bring in top talent.
The 90-Day Sales Team Turnaround Plan
Month 1: Diagnosis & Clean-up
- Audit every deal over 270 days old.
- Implement strict qualification criteria.
- Score your entire pipeline.
- Conduct in-depth audits of sales processes and tools.
- Collect and analyze key performance data.
- Get feedback from reps and stakeholders.
- Assess the relationship between leadership and reps.
- Review pipeline generation and lead generation quality. 79% of MQLs never convert into sales. (Source: MarketingSherpa)
Month 2: Process Optimization
- Map your buyers’ actual journey (not what you think it is)
- Build playbooks for each buyer persona
- Create battle cards for competitive deals
- Address low-hanging inefficiencies
- Partner with Marketing and foster strong relationships
Month 3: Execution & Accountability
- Weekly pipeline reviews (yes, every single week)
- Weekly win/loss analysis
- Bi-weekly skills coaching
- Roll out refined processes across the team
- Monitor improvements and make iterative adjustments
- Foster a culture of accountability and continuous learning
The results? Companies that follow this plan see:
- 30% shorter sales cycles
- 40% higher win rates
- 25% larger deal sizes
Waiting is Expensive
Salesforce research shows that 53% of sales professionals find it more challenging to sell than a year ago, potentially leading to missed revenue opportunities. Here’s the uncomfortable truth: Every month you wait to fix your sales team is costing you real money.
A 100-person enterprise software company with a broken sales process is losing $2.5M in revenue every quarter.
That’s not revenue you can make up later. That’s revenue that’s gone forever.
But it gets worse: Your best salespeople are probably already looking for their next opportunity.
Top performers know when a sales org is broken. They’re usually gone before leadership notices the problem.
The question isn’t whether you need to fix your sales team. The question is: Can you afford not to?
What to do right now:
- Calculate your true sales cycle length
- Audit your last 10 lost deals
- Check your team’s competitive win rate
- Determine your pipeline roadblocks and start fixing them
Sustaining Success Beyond Quotas
A healthy sales team goes beyond hitting quota; it requires a foundation that supports sustainable growth and consistency. Focusing solely on processes and mechanics won’t cut it.
Strong internal relationships and seamless collaboration with sales enablement and marketing are key to long-term success. A well-connected team drives better outcomes and adapts more effectively to changing market conditions.
What challenges are you facing with your enterprise sales team right now?
