Why Your Sales Reps Underperforming Growing Pipeline

A larger sales pipeline seems like a win. It suggests your marketing efforts are working, demand is high, and your business is on the right track. But what if your sales team is struggling to close deals? You’re not alone. Many sales leaders find themselves frustrated, asking, “Why are my sales reps underperforming growing pipeline?” This common paradox, especially in the competitive IT sales landscape, points to deeper, systemic issues that a bloated pipeline can often hide.

According to a 2024 HubSpot Sales Strategy Report, a significant number of sales leaders say their teams miss quotas even with a robust pipeline. This disconnect shows that a pipeline’s size doesn’t guarantee success; it’s what happens inside that funnel that truly matters. This article will explore the core reasons behind this problem and provide actionable solutions to fix it.

The Real Reason Sales Reps Underperforming Growing Pipeline

The core issue isn’t a lack of opportunities; it’s a breakdown in the process and a lack of proper enablement. Here are the key factors contributing to this problem:

• Unqualified Leads Inflate the Numbers

Many teams confuse activity with effectiveness. They fill their pipelines with a high volume of leads, but the quality is often low. This means your sales reps spend valuable time and energy chasing prospects with no real buying intent. A B2B SaaS sales director in San Jose noted, “We found that 40% of our pipeline had no real buyer intent.” When reps work on low-intent prospects, their closing rates will naturally drop. McKinsey’s Technology Trends 2025 report highlights that high-growth tech firms that prioritise lead qualification report 1.8x higher win rates.

• A Lack of Targeted Rep Training

Sales rep performance often suffers when companies scale rapidly without updating their training. A 2023 LinkedIn Learning report revealed that only 27% of sales reps receive quarterly skill training. In IT sales, where solution complexity is high, a lack of continuous training leads to misaligned messaging and missed opportunities. Deloitte’s research shows that IT sales teams that invest in continuous training improve quota attainment by 50%. A mid-sized IT firm, NexGen Solutions, customised their pitch decks by vertical and implemented weekly peer-led training reviews. As a result, their close rates rebounded to 25%, and their average deal size grew by 18%.

• Stagnation in the Middle of the Funnel

Many sales reps struggle not with generating leads but with advancing them through the middle stages of the sales process, from demo to proposal. This is often due to poor discovery calls or an inability to clearly communicate the return on investment (ROI). Forrester’s research shows that only 23% of B2B buyers feel that sellers demonstrate a clear understanding of their business problems, a major contributor to sales reps underperforming growing pipeline.

1. Overweighting Top-of-Funnel Metrics

Sales managers can sometimes focus too much on a large pipeline to impress leadership or meet dashboard goals, without critically analysing conversion ratios. This leads to a situation where the wrong reps are chasing the wrong deals. A VP of Sales at a cloud infrastructure provider shared, “We had a 2x increase in pipeline value over two quarters—but our win rate dropped by 35%. That told us the wrong reps were chasing the wrong deals.”

2. Inefficient Sales Processes and Lack of Motivation

According to a 2024 Salesforce State of Sales Report, only 30% of companies review pipeline stages weekly, which leads to bloated and outdated pipelines. Inefficient sales processes and unclear next steps bog down reps and decrease their productivity. Furthermore, a 2022 McKinsey study found that high-performing sales teams are 1.5 times more likely to have clear, performance-based incentives. A lack of motivation and clear goals can be a key reason sales reps underperforming despite a growing pipeline.

3. Expert Insights and Future Trends

“Sales leaders need to move beyond rep-based blame. Underperformance is often a process failure—deal reviews, training loops, ICP alignment. If you fix the system, you fix the output,” says Anjali Mehra, ex-Chief Revenue Officer at a global SaaS company. She recommends mapping rep behaviors to pipeline health, not just win/loss rates.

As AI reshapes IT sales, smart enablement will be the differentiator. By 2027, Gartner predicts 75% of B2B sales interactions will occur through digital channels. AI-powered tools are already helping businesses identify stuck deals and predict lead conversion rates. Businesses that leverage these tools and focus on developing their teams’ skills in virtual selling and data analysis will be the ones that succeed.

4. Actionable Recommendations for Sales Leaders

If your sales reps underperforming despite a growing pipeline, here’s what you can do to turn things around:

• Audit Pipeline Quality Monthly: Implement a robust qualification checklist to remove dead leads early. Use a buyer-first qualification framework that goes beyond simple metrics.
• Invest in Continuous Training: Implement regular rep training programs focusing on consultative selling, technical expertise, and objection handling.
• Streamline Your Sales Process: Audit your pipeline for bottlenecks. Adopt CRM tools to ensure reps follow a clear, repeatable process.
• Customise Pitches and Strategies: Move away from a one-size-fits-all approach. Equip your team with insights into buyer personas and industry trends, so they can customise their outreach and pitches to build trust and relevance.
• Track Win Rates by Rep: Go beyond stage-based metrics and track win rates by rep to spot systemic underperformance and coaching opportunities.
• Leverage AI-Driven Insights: Use technology to identify deals that are stalling and provide targeted coaching.

Final Thought

A growing pipeline is a powerful asset, but only if your team is equipped to handle it effectively. The next time you see your pipeline growing, ask yourself a tougher question: are my sales reps actually progressing the right deals? Sales reps underperforming despite a growing pipeline is not just a performance problem; it’s a leadership opportunity to rewire your system, upgrade your strategy, and drive real revenue impact.

About LawCrust

LawCrust Global Consulting Ltd. delivers cutting-edge Hybrid Consulting Solutions in Management, Finance, Technology, and Legal Consulting to ambitious businesses worldwide. Recognised for our cross-functional expertise and hybrid consulting approach, we empower startups, SMEs, and enterprises to scale efficiently, innovate boldly, and navigate complexity with confidence. Our services span key areas such as Investment Banking, Fundraising, Mergers & Acquisitions, Private Placement, and Debt Restructuring & Transformation, positioning us as a strategic partner for growth and resilience. With an integrated consulting model, fixed-cost engagements, and a virtual delivery framework, we make business transformation accessible, agile, and impactful.

For expert legal help, please contact us:

• Email: inquiry@lawcrustbusiness.com