What Are the Biggest Challenges in Our Current Sales Process, and How Can We Overcome Them?

“If your SaaS sales process isn’t evolving, it’s decaying.” That’s how Jason Lemkin, founder of SaaStr, framed the challenge facing SaaS CEOs today. In a market where customer expectations shift faster than your product roadmap, and where valuation multiples hinge on sales efficiency, understanding—and fixing—your sales bottlenecks is no longer optional. It’s existential.

Drawing on research from elite MBA programs like Harvard and Wharton, insights from SaaS leaders, and data from sources like McKinsey and SaaS Capital, this article unpacks the most pressing sales challenges SaaS companies face—and how to overcome them with evidence-based strategies.

1. Misaligned Metrics: When KPIs Undermine Growth

One of the most common issues in SaaS sales is tracking the wrong metrics—or tracking the right ones in isolation. According to a recent iMerge Advisors guide on SaaS KPIs and valuation multiples, companies that focus solely on top-line ARR growth often miss critical signals like CAC payback period, net revenue retention (NRR), and sales cycle length.

Solution: Build a Balanced KPI Dashboard

Stanford’s MBA curriculum on innovation metrics recommends a balanced scorecard approach. For SaaS sales, this might include:

• Customer Acquisition Cost (CAC) and LTV:CAC ratio – Target a ratio of 3:1 or better.
• Sales Cycle Length – Shorten by segmenting leads and automating qualification.
• Net Revenue Retention (NRR) – Aim for 120%+ to signal strong upsell/cross-sell motion.
• Win Rate by Segment – Identify where your reps are most effective.

Companies that track these metrics in tandem can better align sales with product, marketing, and customer success—improving both efficiency and valuation.

2. Inefficient Lead Qualification and Handoff

According to McKinsey’s 2023 SaaS growth report, 30–50% of MQLs never convert due to poor qualification or delayed follow-up. This is often a result of misaligned marketing and sales teams, or outdated lead scoring models.

Solution: Automate and Align

Wharton’s research on sales funnel optimization suggests integrating AI-driven lead scoring tools (like MadKudu or 6sense) to prioritize high-intent leads. Pair this with a service-level agreement (SLA) between marketing and sales that defines:

• Lead response time (e.g., within 5 minutes)
• Qualification criteria (firmographics, behavior, intent)
• Ownership of lead stages

Companies that implement this alignment see up to 20% higher conversion rates, per SaaS Capital benchmarks.

3. Stalled Deals and Long Sales Cycles

For mid-market SaaS firms ($5M–$50M ARR), long sales cycles are a silent killer. Deals stall due to unclear ROI, lack of urgency, or too many decision-makers. Harvard Business School’s case studies on B2B SaaS sales highlight that the average B2B deal involves 6.8 stakeholders—each with different priorities.

Solution: Sell the Business Case, Not Just the Product

Equip your sales team with ROI calculators, case studies, and business impact decks. Use MEDDIC or Challenger frameworks to uncover pain points and build consensus. And consider deploying deal acceleration tools like Mutual Action Plans (MAPs) to keep stakeholders aligned and accountable.

Advisors like iMerge often use these frameworks during M&A due diligence to assess sales scalability—so embedding them now can also boost your exit readiness.

4. Underutilized Technology Stack

Many SaaS companies invest in CRMs, sales engagement platforms, and analytics tools—but fail to integrate or fully utilize them. A 2023 SaaS Capital survey found that 42% of sales teams use less than half the features in their tech stack.

Solution: Audit and Streamline Your Sales Tech

Conduct a quarterly tech stack audit. Ask:

• Which tools are actively used by reps?
• Where are there redundancies or gaps?
• Are we capturing and analyzing the right data?

Then, invest in enablement. According to research from the Kellogg School of Management, companies that train reps on tool usage see a 15–20% increase in productivity.

5. Churn and Poor Post-Sale Handoff

Sales doesn’t end at the close. If your handoff to customer success is weak, you’ll see higher churn and lower NRR—both of which drag down valuation. As explored in this iMerge article on CLTV and retention, acquirers scrutinize post-sale engagement metrics when assessing SaaS deals.

Solution: Create a Seamless Onboarding and Expansion Path

Use a “land and expand” playbook. Ensure sales captures key implementation details and success metrics during the sales process, then passes them to customer success. Track:

• Time to first value (TTFV)
• Product adoption rates
• Customer health scores

Companies that excel here often see 30–50% higher upsell rates and stronger M&A interest.

6. Talent Gaps and Sales Team Turnover

High rep turnover—common in SaaS—leads to inconsistent pipeline coverage and lost institutional knowledge. According to a Wharton study, the average SaaS AE tenure is just 18 months.

Solution: Invest in Sales Enablement and Career Pathing

Top-performing SaaS firms implement structured onboarding, continuous training, and clear promotion paths. Consider:

• Quarterly skill assessments
• Peer coaching programs
• Incentives tied to both revenue and customer outcomes

These practices not only improve performance but also reduce attrition—critical for maintaining momentum during growth or preparing for a strategic exit.

7. Lack of Sales Forecasting Accuracy

Inaccurate forecasts erode investor confidence and hinder strategic planning. As highlighted in iMerge’s guide to financial forecasting tools, poor visibility into pipeline health can also derail M&A negotiations.

Solution: Implement Data-Driven Forecasting Models

Use historical conversion rates, deal stage velocity, and rep performance data to build predictive models. Tools like Clari or InsightSquared can help. Also, align sales forecasts with finance and product roadmaps to ensure cross-functional accountability.

Conclusion: Sales Efficiency Is a Strategic Lever

Fixing your sales process isn’t just about hitting this quarter’s number—it’s about building a scalable, acquirable business. Whether you’re targeting a $50M ARR milestone or preparing for a liquidity event, sales efficiency directly impacts valuation, cash flow, and strategic optionality.

As explored in Exit Business Planning Strategy, firms that optimize their sales engine early are better positioned for premium exits and smoother due diligence.

Scaling fast or planning an exit? iMerge’s SaaS expertise can guide your next move—reach out today.