Top 10 Challenges in B2B Sales And How to Overcome Them

B2B sales have never been more complex. Today's sales teams navigate longer sales cycles, multi-stakeholder buying committees, intricate pricing structures, and heightened buyer expectations, all while trying to close deals faster than ever. These challenges in b2b sales aren't just frustrating; they directly impact your revenue, team morale, and ability to scale predictably.

The reality is that many of these obstacles stem from operational friction, manual quoting processes, pricing errors, deal approval bottlenecks, and disconnected systems that slow your team down when speed matters most. While strategy and skills are important, the tools your sales team uses play a crucial role in determining whether they succeed or struggle.

In this guide, we'll walk through the top 10 challenges in b2b sales that high-growth SaaS companies face today, and show you how to overcome sales challenges with practical, actionable strategies. We'll explore everything from lead qualification issues to complex pricing negotiations, and demonstrate how modern CPQ and deal desk solutions like Subskribe's AI-powered platform can eliminate operational roadblocks and empower your team to close more deals with less friction.

Challenge 1: Manual Quoting, Pricing, and Approval Delays

One of the most common challenges in B2B sales is the time-consuming and error-prone process of configuring price quotes and obtaining their approval. If your sales team is still building quotes manually in spreadsheets or navigating clunky legacy systems, you know exactly what this looks like.

A rep finishes a great discovery call and needs to generate a quote. They spend hours piecing together product configurations, hunting down pricing tiers, calculating discounts, and cross-referencing approval matrices. Then they submit the quote for approval, where it sits in someone's inbox for days. Meanwhile, the prospect is waiting, and your competitor just sent their proposal.

The real cost isn't just time lost. Manual quoting introduces pricing errors that can cost you margin, create fulfillment headaches, or worse, erode trust with your buyer. When quotes contain mistakes or take too long to arrive, you signal that doing business with you will be complicated.

How to Overcome Sales Challenges Like Manual Quoting

The path forward is clear: adopt a CPQ tool that automates quote configuration, applies pricing rules consistently, and streamlines approval workflows. Modern CPQ platforms eliminate the manual work that slows your team down and introduces errors.

Subskribe's Deal Desk AI and CPQ platform make a tangible difference. Your sales team can generate accurate, professional quotes in minutes instead of hours. The system automatically applies your pricing rules, discount guidelines, and product configurations, eliminating manual errors before they happen. Intelligent approval workflows route deals to the right stakeholders instantly based on deal size, discount levels, or custom terms, cutting approval time from days to hours.

The result? Faster response times, fewer pricing mistakes, and shorter sales cycles that help you close more deals.

Challenge 2: Inconsistent Proposals and Lack of Standardization

Another critical challenge in b2b sales is the chaos that comes from inconsistent proposal creation. When each sales rep builds proposals from scratch or uses their own version of "the template," your company presents a fragmented face to prospects and that inconsistency undermines trust.

One rep sends a proposal with your old logo and outdated product descriptions. Another uses last quarter's pricing structure because they're working from a saved copy. A third creates a beautiful custom deck but accidentally quotes terms your legal team hasn't approved. Every proposal looks and feels different, making your organization appear disorganized.

The problem extends beyond branding. When proposals aren't standardized, you lose visibility into what's actually being sent to prospects. Which pricing table version are reps using? What discount levels are they quoting? Without centralized control, these questions become impossible to answer until a deal goes sideways.

How to Overcome Sales Challenges Through Standardization

The solution is to standardize templates, centralize proposal metrics, and monitor versioning across your sales organization. When everyone works from approved, up-to-date templates, you ensure brand consistency, pricing accuracy, and legal compliance on every deal.

Subskribe addresses this directly with a centralized proposal library that gives your entire sales team access to approved, current templates. Every proposal pulls from the same source of truth for pricing, product descriptions, and terms. The platform tracks version history automatically, so you always know which proposal version was sent to which prospect and when.

When your proposals are standardized, you project professionalism, reduce risk, and make it easier for prospects to say yes.

Challenge 3: Lack of Buyer Insights and Visibility Into Buyer Behavior

One of the most challenging sales challenges modern teams face is operating in the "dark funnel", the space where buyers research, evaluate, and make decisions without your sales team having any visibility into what's happening.

You send a proposal and then... silence. Did they open it? Did they share it with other stakeholders? Which sections did they review? Who else in their organization is involved? Without answers, your sales reps are flying blind, guessing when to follow up and what to say.

This lack of visibility becomes especially problematic in complex B2B deals with multiple stakeholders. Your primary contact might love your solution, but if the CFO never opens the pricing section or the VP of IT has concerns you don't know about, your deal can stall without warning.

How to Overcome Sales Challenges With Buyer Intelligence

The key is capturing engagement analytics and buyer interaction data throughout the sales process. When you understand who's engaging with your content, what they're focusing on, and how stakeholders are interacting with your proposals, you can tailor your outreach with precision instead of guesswork.

Subskribe's built-in analytics and Deal Desk AI provide exactly this visibility. The platform tracks stakeholder engagement at the deal level, showing you who opened your proposal, which sections they reviewed, how long they spent on pricing versus terms, and which additional stakeholders have been brought into the conversation. This intelligence empowers your reps to follow up strategically and engage the right people at the right time.

When you can see what your buyers are doing, you can respond with exactly what they need to move forward.

Challenge 4: Misalignment Between Sales Process and Buyer's Journey

A major challenge in b2b sales that many organizations overlook is the fundamental mismatch between how they want to sell and how buyers actually want to buy. Your sales process might be designed around your internal needs: discovery calls, demos, technical evaluations but if that sequence doesn't match the buyer's natural journey, you create friction at every step.

Your process requires a 60-minute demo before discussing pricing, but your buyer has already done extensive research and just wants to see if you're in their budget range. Or your workflow pushes prospects toward annual contracts when they need to start with a quarterly pilot. When your process fights against the buyer's preferences, deals drag on or fall apart.

The problem intensifies in complex B2B sales where multiple stakeholders are involved. While you're focused on your economic buyer, the technical team needs detailed implementation specs, procurement needs specific contract terms, and finance needs usage projections.

How to Overcome Sales Challenges Through Buyer-Centric Design

The solution is mapping your buyer's actual journey and aligning your sales process to match it. This means understanding the steps buyers naturally take, the information different stakeholders need at each stage, and the flexibility required to support various buying motions.

Subskribe's configurable CPQ workflows allow you to mirror the buyer's step-by-step process rather than forcing them into your rigid framework. The platform supports multi-stakeholder alignment by enabling different views and information for technical evaluators, financial decision-makers, and executive sponsors, all within the same deal. You can configure workflows that accommodate pilots, phased rollouts, or immediate enterprise deployments.

When your sales process matches how buyers want to buy, deals move faster and close more predictably.

Challenge 5: Long Sales Cycles and Stalled Deals

Long, drawn-out sales cycles are among the most persistent challenges in b2b sales. What should take weeks stretches into months. Deals that seemed promising suddenly go quiet. Your pipeline looks healthy on paper, but velocity tells a different story, too many opportunities stuck in limbo.

The complexity inherent in B2B sales drives this problem. Multiple stakeholders need to align. Budget approval processes drag on. Technical evaluations take longer than expected. Procurement introduces new requirements late. Each of these steps adds time, and when they're not well coordinated, momentum dies.

The real danger isn't just the time lost, it's the increased risk that comes with every passing week. Longer sales cycles mean more opportunities for competitors to enter the picture, for budgets to get reallocated, or for your champion to leave the company.

How to Overcome Sales Challenges With Momentum Management

The key is breaking your sales cycle into clear milestones, maintaining momentum at each stage, and removing friction that causes unnecessary delays. Focus on shortening decision windows by making it easy for buyers to say yes at each step.

This is where operational efficiency becomes critical. When your team can generate quotes instantly, get approvals in hours instead of days, and respond to buyer questions without delay, you compress your sales cycle naturally. Subskribe's CPQ and automated approval workflows eliminate the administrative bottlenecks that add days or weeks to deals.

Shorter cycles mean more closed deals and more predictable revenue.

Challenge 6: Multiple Decision-Makers and Stakeholder Management

Navigating multiple decision-makers is one of the trickiest sales challenges in modern B2B environments. Today's enterprise deals routinely involve six to ten stakeholders, each with their own priorities, concerns, and criteria for success.

Your champion in sales operations loves your solution's efficiency gains. The CFO wants to see clear ROI and cost containment. IT needs assurance about security and integration complexity. Legal has questions about data privacy. Procurement wants volume discounts. Each stakeholder can derail your deal if their specific concerns aren't addressed.

The challenge intensifies when stakeholders don't communicate well internally. You might think you've addressed the technical team's questions, only to discover weeks later that they never shared your answers with the security team.

How to Overcome Sales Challenges in Multi-Stakeholder Deals

Success requires identifying all stakeholders early in the process, tailoring your value proposition to each person's specific priorities, and actively facilitating consensus-building across the buying committee.

Subskribe's unified deal desk view helps you manage this complexity by tracking stakeholder engagement at the deal level. You can see which stakeholders have reviewed proposals, what sections they focused on, and where questions or concerns might exist. This visibility allows your team to coordinate outreach strategically and identify potential objections before they become deal blockers.

When you orchestrate stakeholder alignment instead of hoping it happens organically, deals close faster.

Challenge 7: Budget Constraints and Pricing Objections

"It's not in our budget," and "we're already working with another vendor" are objections every B2B sales rep has heard countless times. Budget constraints represent one of the most common challenges in b2b sales, and they're rarely as simple as they sound on the surface.

Sometimes the budget issue is real; there genuinely isn't funding allocated for your solution this fiscal year. But more often, the objection signals something else: the prospect doesn't yet see enough value to justify the investment, or they can't envision how to structure the purchase within their existing budget framework.

The incumbent vendor challenge adds another layer. Even if prospects are frustrated with their current solution, switching costs, both financial and operational, create significant inertia.

How to Overcome Sales Challenges Around Budget and Price

The key is making the business case irrefutable through clear ROI demonstration, offering flexible pricing structures that fit within budget realities, and enabling phased implementations that reduce upfront investment and risk.

This requires presenting pricing options, not just a single price point. Subskribe's CPQ enables exactly this flexibility through scenario-based pricing that lets you model different configurations, payment structures, and implementation approaches on the fly. You can show annual versus monthly pricing, demonstrate volume discounts, structure phased rollouts, or create custom payment terms, all within minutes. The platform's discount workflow management ensures you stay within approved parameters while giving prospects the flexibility they need.

When you can adapt your pricing to match budget realities without sacrificing margins, you turn price objections into closed deals.

Challenge 8: Sales and Marketing Misalignment

One of the most frustrating challenges in b2b sales doesn't come from prospects; it comes from within your own organization. When sales and marketing teams operate in silos, everyone suffers. Marketing generates leads they believe are qualified, while sales complains the leads are garbage. This disconnect wastes budget, damages morale, and costs you real opportunities.

Sales reps spend hours chasing leads that were never properly qualified, following up with contacts who downloaded a whitepaper but have no budget or buying authority. Meanwhile, marketing has no visibility into which leads have actually converted, so they keep investing in channels that don't drive pipeline.

The root cause is usually structural: different goals, separate technology stacks, and no shared accountability for revenue outcomes.

How to Overcome Sales Challenges Through Revenue Alignment

The solution requires aligning teams around shared processes, joint metrics that focus on revenue outcomes, and integrated technology that creates visibility across the entire customer journey.

While CPQ isn't traditionally seen as a sales-marketing alignment tool, Subskribe's integration capabilities with CRM and RevOps platforms create smoother hand-offs between teams. When marketing can see which lead sources convert to closed deals with the best pricing and margins, they optimize toward revenue, not just volume.

When sales and marketing operate as one revenue team, your entire go-to-market engine becomes more efficient.

Challenge 9: Adapting to Changing Buyer Behavior and Digital Environment

The B2B buying process has fundamentally shifted, creating new sales challenges that traditional approaches can't solve. Today's buyers conduct extensive research independently before ever engaging with sales. By the time they reach out, they've already consumed dozens of pieces of content, evaluated multiple vendors, and formed strong opinions, all without speaking to a single rep.

This means sales teams have fewer touchpoints and less influence over the buyer's journey than ever before. The old playbook of building relationships through multiple discovery calls and demos no longer matches how buyers prefer to buy. They want information on demand, at their own pace, without being forced into a vendor-controlled sales process.

Modern buyers expect digital experiences that match what they get in their personal lives: instant pricing, configurability, and the ability to explore options without talking to someone.

How to Overcome Sales Challenges in the Digital Era

The solution is embracing digital-first selling by offering self-service tools that empower buyers to research and configure solutions independently, personalizing content based on behavior, and using data-driven insights to know when and how to engage.

Subskribe's digital quoting portals and self-service dashboards enable exactly this modern buying experience. Buyers can explore pricing scenarios, configure solutions, and generate quotes on their own timeline while you maintain visibility into their activity and can engage strategically when they signal buying intent.

Meeting buyers where they are, digitally, is no longer optional; it's table stakes.

Challenge 10: Technology Adoption and Internal Capability Gaps

The final challenge in b2b sales is one that organizations create for themselves: implementing new technology that's supposed to help sales teams, but instead becomes a source of friction and frustration. You invest in a new CRM, CPQ platform, or analytics tool with high hopes of driving efficiency, only to watch adoption rates stall because the system is clunky, training is inadequate, or the tool doesn't integrate with existing workflows.

Reps avoid using the new CPQ system and revert to building quotes in spreadsheets because it's faster, even though it defeats the entire purpose of the investment. Sales managers can't get accurate pipeline visibility because reps aren't updating the CRM consistently.

The root cause is rarely the technology itself. It's usually a combination of poor user experience, insufficient training, and solutions that don't integrate seamlessly with the tools teams already use.

How to Overcome Sales Challenges in Technology Adoption

Success requires investing in comprehensive training programs, choosing solutions with intuitive user experiences that minimize learning curves, and selecting technologies that integrate naturally with your existing stack.

Subskribe addresses this directly with a user-friendly interface designed specifically for sales teams, not just administrators. The platform offers robust onboarding support and training resources to accelerate adoption. Because Subskribe integrates seamlessly with leading CRM and RevOps platforms, reps work within familiar environments rather than jumping between disconnected systems.

When technology adoption is smooth, your entire sales organization becomes more capable and productive.

Conclusion: Turning Sales Challenges Into Competitive Advantages

The challenges in b2b sales we've explored, from manual quoting delays and inconsistent proposals to multi-stakeholder complexity and technology adoption barriers, aren't going away. If anything, B2B sales will only become more complex as buying committees expand, procurement processes tighten, and buyer expectations continue to rise.

But here's the critical insight: every one of these sales challenges is solvable. Success doesn't require a complete overhaul of your sales organization or superhuman reps. It requires the right combination of process optimization, team enablement, and purpose-built technology that removes friction from your sales motion.

The organizations winning in today's competitive landscape aren't the ones with the biggest sales teams or the flashiest marketing. They're the ones who've systematically addressed operational bottlenecks, armed their teams with tools that accelerate rather than hinder their work, and created buying experiences that match modern expectations.

This is exactly what Subskribe's CPQ and Deal Desk AI platform is designed to do. Whether you're struggling with slow quote generation, pricing errors, approval bottlenecks, lack of deal visibility, or stakeholder alignment challenges, Subskribe provides the infrastructure to move faster, sell smarter, and close more deals with less friction.

The question isn't whether you'll face these challenges in b2b sales you will. The question is whether you'll proactively address them or let them continue costing you deals, revenue, and competitive position.

Ready to see how Subskribe can transform your sales process? Book a demo to explore how our AI-powered CPQ platform helps high-growth SaaS companies accelerate deals and scale efficiently!

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