7 biggest sales challenges of 2024 (and how to solve them)

2023 threw some unexpected curveballs at sales teams. And we're still not sure what 2024 will look like.

The unpredictable economy has made companies more selective about their investments, leading to reduced budgets. 

Add to this a shifting sales funnel blueprint, inaccurate sales forecasting, and technology overload, and you'll find yourself amidst the perfect sales storm.

But even during uncertain times, growth opportunities exist. From leveraging the buyer champion to creating new data streams, there's a lot you can do to overcome the biggest sales challenges of 2024.

We've compiled a list of the seven biggest challenges sales teams should be prepared for this year based on our conversations with other sales leaders. Along with this list, we'll also provide actionable solutions to address these challenges and drive sales performance.

1. Buyers want information, not conversations

The digitization of B2B has transformed the sales landscape, resulting in a change in buyer behavior and shorter sales conversations.

In the past, buyers sought sales conversations to make informed purchase decisions. As much of that information is now available online, they’re now spending less time engaging with salespeople and more time researching solutions online on their own.

Gartner reports that buyers spend only 17% of their buying time talking to potential suppliers, while they spend 27% of their buying time researching solutions online. 

This shift in behavior has a significant impact on your sales team's ability to influence purchase decisions—and underscores the importance of having a strong buyer champion who can cut through the noise and advocate for your product. 

Solution: Buyer enablement through digital sales rooms

Buyer enablement operates under the premise that the B2B purchasing process is complex and mostly executed by buying teams who prefer operating independently. 

It focuses on providing buyers with the necessary content, tools, and support to:

• Understand the biggest problems/pain points they’re trying to solve
• Learn how your product uniquely solves these problems/pain points 
• Create a clear path to purchasing the right solution

This “enables” the buyer to make informed purchase decisions, making them less likely to experience buyer's remorse. 

Buyers are three times less likely to regret a large purchase when sellers provide high-quality knowledge that informs their purchase process, according to Gartner.

To approach buyer enablement strategically, you can use digital sales rooms (DSRs). 

DSRs let you curate and host all the core content that's shared during the sales process, such as sales proposals and demo videos. This allows potential customers to do their own research and makes it easier for the buyer champion to advocate for your product internally. 

Instead of forwarding a ton of documents and links, the champion can send a single link to their team to guide the decision-makers toward your product.

‍💡 Related reading: Learn how to personalize sales at scale with a digital sales room.

2. The buyer journey isn't linear anymore

The traditional buying stages have faded, demolishing the one-way funnel approach and blurring the line between marketing and sales. 

The traditional sales model, where marketing content would support the buyer until they were ready to speak to sales professionals, is no longer effective. 

Instead, sales and marketing teams must collaborate to support buyers throughout the buying process.

This has forced sales leaders to reassess their sales strategy. 

For any complex B2B solution, there are about six-to-ten decision-makers, each armed with the information they have independently researched online. This means more viewpoints on problem identification, requirements building, and supplier selection, making it harder than ever to reach a consensus and slowing down deal velocity.

To complicate matters further, new industry information is continually emerging, causing buyers to reevaluate past decisions and uncover new obstacles. 

Solution: Leverage the buyer champion 

Having a strong and qualified buyer champion is critical to winning a deal within a prospective customer's company. They can strategically highlight your product's best features during closed-door conversations, increasing your chances of success.

In addition, they:

• help sales identify the prospective company’s decision-makers and provide crucial insight into their specific needs and pain points 
• work with marketing to develop relevant sales collateral that is aligned with the prospective company’s buying process

Without this person, you can kiss the sale goodbye. But you must properly leverage your buyer champion to reap the benefits. 

This involves training them on how to effectively communicate your product’s value to internal stakeholders and decision-makers and providing them with buyer enablement resources and sales collateral to support their efforts.

💡 Related reading: Check out our proven strategies to empower your buyer champion. 

Solution: Account mapping and multithreading

Enterprise sales can be challenging, especially because it isn't always clear who is involved in the buying process beyond your main point of contact.

That's where account mapping comes into the picture. By visualizing the entire deal, you can identify potential champions, blockers, and influencers and create strategic plans to build consensus among the entire buying committee.

Although it's a comprehensive process that involves understanding your CRM data, building organizational charts, and identifying key relationships, creating account maps is worth the effort as it helps simplify the B2B buying process.

In addition to account mapping, consider multithreading to build relationships across the prospect's organization. 

Your champion can introduce you to all the key stakeholders, or you can reach out to them yourself through cold outreach on LinkedIn. 

By having multiple connections within the prospect organization, you reduce the risk of your deal hinging on a single person. This approach also creates strategic alignment between your organizations and cements your product's value.

🧠 Multithreading tip: When building personal connections, focus on establishing rapport instead of discussing the details of the deal. This approach will help you foster long-term relationships with prospects.

3. Uncertain prospect budgets and reduced spending

2022 saw rising inflation and big interest rate hikes, and Deloitte predicts the impact of those hikes will last into 2023. Then there's also the issue of the tight labor market potentially accelerating wage growth, further contributing to the already uncertain economic environment.

This uncertain economic environment means buyers are likely to do more budget cuts and reduce spending, which can result in a mismatch between budget expectations and reality.

When budgets are uncertain, sales pipeline forecasting becomes complicated. Buyers tend to delay their purchasing decisions, making it difficult for sales reps to meet their sales targets. 

Prospects may also be hesitant to make purchasing decisions, leading to pushback on pricing, which further slows down the sales process.

In tight-budget situations, buyers tend to focus on the price of a solution rather than its overall value. 

Therefore, reps must work harder to:

1. demonstrate their product's value as an essential, not nice-to-have service
2. include proof of ROI in the sales pitch (that can convince the CFO, not just the buyer champion)

Solution: Share case studies and ROI studies

As a sales leader, you need to be more strategic and focused on demonstrating your product’s value and ROI in terms of the prospect’s key pain points and challenges. And what better way to do this than by providing them with case studies and ROI studies?

Case studies allow you to share compelling stories highlighting your product's role in helping past customers overcome challenges, as well as the specific results they achieved. 

By showcasing real-world examples, prospects can better understand how your product can help them achieve their sales goals.

ROI studies can further strengthen your case. By comparing your product's cost against its projected benefits, ROI studies enable prospects to accurately assess your solution's tangible business value in terms of its financial impact. For instance, ROI studies can demonstrate how your product can help increase profitability, improve sales productivity, or generate more qualified leads.

💰 ROI study example: You can create an ROI impact study even if you don’t have hard numbers that show revenue proof. Check out our own article on The Business Impact of Dock as an example.

Solution: Run POC projects to prove value

A sales proof of concept (POC) is a low-cost, low-risk starter project that goes beyond a standard product or software trial, where you run a test project for your client while providing hands-on implementation and technical support. 

With a POC, you can showcase your product's real-world value and potential ROI, helping you get your foot in the door and create a wedge into future business.

To start, take the time to understand the prospect's needs and goals. Agree on a clear definition of what success means for both parties. Once the success criteria are in place, shift your focus to executing and delivering the promised results.

Throughout the POC, maintain close collaboration and communication with the prospect. Use this opportunity to address any lingering concerns or objections they may have. This will pave the way for a seamless transition to becoming a paying customer and establish the foundation for a long-term, mutually-beneficial relationship.

🧩 Get the template: Get Dock's sales POC workspace template here or check it out below.

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Solution: Shift your sales focus to customer retention

Create a customer-centric culture focused on customer retention and expansion and client management to build and nurture long-term, positive relationships.

Instead of solely relying on new customers, identify the needs of your current customers and accordingly deliver excellent service. You can also offer value-added services like free training, access to exclusive events or content, and consulting services to differentiate yourself from competitors and build trust.

Note that customer renewals are a revenue team-wide effort, where your sales, marketing, and success should work in tandem to promote retention.

Additionally, prioritize strengthening your client management processes to maintain a high level of communication, transparency, and accountability with customers. 

Provide regular updates on product offerings and pricing, collect and implement customer feedback, and promptly address any concerns or issues necessary to keep clients with your organization for longer.

This approach also creates new upselling and cross-selling opportunities, where you can offer customized solutions addressing those needs to get more satisfied customers and increase revenue.

4. Inaccurate sales forecasting

Sales forecasting is a necessary selling skill that helps build better products, understand targeted customer segments, and improve product positioning to close deals faster. 

However, the increasingly complex B2B buying process with restricted sales conversations and reduced or uncertain budgets has made accurate forecasting significantly harder.

Let’s quickly recap why:

• Because buyers rely more on their own research and less on face-to-face sales conversations, sales reps can less reliably forecast whether a deal will close.
• Complex buying processes mean the traditional deal stages are murkier and more difficult to measure.
• When prospects are uncertain about their budgets or actively cutting back on spending, they are less likely to invest in new products or sales. 
• This results in longer sales cycles, smaller deal sizes, and lower revenue, as well as creates an air of uncertainty around deals.

The direct impact of these sales challenges? 

A complex and unreliable environment for sales forecasting—creating significant blind spots when leveraging data and analytics to identify patterns and interests, compromising your competitive edge in the marketplace.

Solution: Create new data streams to better monitor sales

One effective way to counteract forecasting challenges is to look for opportunities to collect more relevant prospect data. 

This will help you make informed decisions concerning your sales team’s daily operations and overall strategy, as well as fill the knowledge gaps and blindspots to reduce losses and increase ROI.

While a CRM is great for tracking core sales data, it may only be compatible with certain data streams (e.g., tools that integrate with it). This creates a need to include new data streams and tools that can help you effectively monitor and forecast sales.

Here’s a list to get started:

• Dock lets you track when your prospects engage with your sales content
• Gong captures and analyzes customer interactions like calls and support texts
• Champify identifies former users of your product at the buyer’s company 
• Mixpanel tracks in-product analytics to predict retention and churn
• Clari provides AI-powered sales forecasting

The key to adopting any tool: connectivity. 

Choose versatile tools like Dock that integrate with popular CRMs so you can combine all data streams into a single source of truth dashboard in your CRM. Otherwise, you’ll have to purchase and implement a new business intelligence (BI) tool to build your own analytics dashboard.

📖 Read more: Read our Sales Monitoring Guide to learn more about building an effective sales monitoring system for growing startups.

5. Cross-team silos

To survive in the long term, an organization must have a cohesive Revenue team made up of Marketing, Sales, and Customer Success. 

Unfortunately, these departments tend to drift apart, functioning independently of one another with insufficient communication, collaboration, and alignment, leading to significant sales challenges.

For instance, sales reps might communicate one message to potential clients, while marketing campaigns promote a different message, and customer success conveys yet another message during onboarding. This misaligned messaging creates confusion, which ultimately leads to a breakdown of trust.

Solution: Drive revenue enablement using cross-functional platforms

The concept of revenue enablement aims to align sales, marketing, and customer success teams for the seamless delivery of customer experiences and revenue growth. This requires focusing on customer retention and expansion, alongside driving new business, by leveraging renewals, upsells, and TOFU leads.

To facilitate better revenue collaboration, you need revenue enablement platforms that foster two-way collaboration between revenue teams like marketing, sales, and customer success to drive revenue and collaboration with customers to drive better outcomes.

Dock offers revenue teams a dedicated platform that can integrate with various tools like a CRM and a CS platform to centralize core information. Moreover, it provides a host of products that enable team members to share product information with team members and supply relevant content to customers, breaking down cross-team silos.

You can talk to our sales team to learn more about how Dock helps cross-functional revenue teams generate revenue as a unified cohesive team.

6. Personalization at scale

For a successful sale, it's crucial to personalize the entire sales process and make the buyer feel valued and taken care of. 

This involves producing custom content and sales decks focused on the prospect’s unique needs and pain points and aligned with their decision-making process. Another important aspect here is building a subset of all the available information so it's easy for the buyer to understand and find value when making purchase decisions.

Unfortunately, the limited buyer-seller interaction time gives you a relatively shorter timeframe to build personal relationships. Add to this the active involvement of several stakeholders and decision-makers with competing priorities and timelines—and you‘re left figuring out how to deliver relevant and personalized content at scale.

Solution: Use a Dock workspace template

With Dock, your team can start from a workspace template and then personalize it lightly to each prospect. Buyers can easily access your Dock workspace without having to create an account themselves—all they need is their email address.

You can begin with Dock's digital sales room template and tailor it to your buyer's specific challenges using the rich-text editor and embedding any necessary sales collateral. 

As your relationship with the buyer progresses, you can add additional content that is most relevant to their current needs.

While other digital sales room tools tend to force you into static, rigid templates, Dock gives you a highly collaborative and flexible platform, allowing for customization at scale.

7. Too many selling tools

Sales teams often use a variety of selling tools, from CRM systems to sales enablement platforms to client portal software, to optimize their sales processes. While these tools provide valuable insights, having too many is never a good idea.

Using multiple tools may lead to inefficiencies in the sales process, resulting in duplicated efforts and slower sales velocity. Even sales reps can get frustrated with having to switch between different tools to complete tasks.

Further, an overabundance of data can cause information overload, leading to analysis paralysis, where reps are uncertain about which metrics to prioritize. Tool integration issues may also arise, leading to unnecessary manual work and increased spending on software.

Solution: Reduce tech clutter

Consider consolidating and simplifying your sales tech stack to overcome tool-related sales challenges.

Instead of relying on multiple individual tools with separate use cases, invest in all-in-one tools or new technologies that integrate with each other. This will enhance your team's sales efforts while reducing tech clutter and saving money. 

A tool like Dock, for example, consolidates your organization's tech stack by combining seven other software categories into one tool. Dock also lets you embed all your various content and tools into one buyer workspace, which reduces the tech clutter for both you and your customer.

Effective sales training is also crucial here. This will help your reps easily navigate challenges that may arise when using your tech stack. 

The key is to use as few tools as possible when selling and closing deals. By doing so, you'll simplify your sales tech stack and help your reps improve efficiency, overcome sales challenges, and ultimately close more deals.

Summary

Here's a quick overview of how you can overcome B2B sales challenges in 2023:

1. Create digital sales rooms to facilitate buyer enablement 
2. Identify and leverage your buyer champion 
3. Implement account mapping and multi-threading strategies
4. Share case studies and ROI studies to build trust
5. Run POC projects to demonstrate product value and ROI
6. Focus on retaining and collaboration with current customers
7. Look for opportunities to collect more sales data
8. Use cross-functional platforms to mitigate team collaboration silos
9. Leverage time-saving templates to personalize at scale
10. Reduce tech clutter by simplifying your sales tech stack

Want to learn more about how Dock can help overcome your organization's biggest challenges? You can schedule a demo with our sales team, or get started for free.