10 Key Sales Challenges for 2024 [+How You Can Overcome Them]

Sales is a dynamic field, and 2023 really put that to the test. AI hit the mainstream, forever changing how we work. On top of that, buyer expectations are evolving, and salespeople need to react to these shifts. 

As we inch closer to 2024, there are a host of new and emerging sales challenges that salespeople have to account for. In the interest of helping you identify and overcome those issues, we reached out to sales experts and conducted some research. 

Here are ten of the main concerns salespeople will face in 2024 — as well as expert perspectives on how to address them.

10 Sales Challenges for 2024

1. Buyers crave personalization

53% of sales professionals believe personalizing the buying process to each prospect will become more important in the future.

In today's competitive market, a one-size-fits-all approach is no longer sufficient; buyers not only want personalization, they expect it.

But how can salespeople go the extra mile to personalize their outreach when time is of the essence?

How to Handle This Challenge

According to Hubspot Strategic Channel Account Manager Chris Moore, it boils down to how effectively you can reconcile personalization and tech acumen. He says, "The salesperson who can leverage technology in a way to personalize that messaging will win in 2024."

He adds, "Because there are so many salespeople reaching out via email and phone calls now as opposed to meeting with people in person, you have to figure out clever ways to get into these businesses with a personalized approach."

Jayme Manos, Principal Manager of Corporate Sales at HubSpot, believes personalization will become a non-negotiable, telling me, "I believe that non-personalized sales email blasts will become even less effective. Reps will need to ensure they've not just researched an account, but that they come with a strong 'point of view' and a very clear call to action, regardless of medium."

2. Finding the right balance with AI

78% of sales professionals believe that AI can make them more efficient at their job, according to HubSpot's 2023 State of AI Report. Yet, most of us are still testing the waters with this technology, and there's plenty of room for missteps along the way. 

Take sales outreach, for example. You could use AI as a content machine to rev up your outreach, but that isn't the best use case.

As Mike Kaput, Chief Content Officer at Marketing AI Institute, told me, "AI is a very powerful tool—one that can definitely help you scale your outreach. However, the same principles still apply: nobody likes to get blasted with tons of irrelevant emails. Just because you can send more outreach using AI doesn't mean you should."

How to Handle This Challenge

If you're feeling pressure to rebuild all of your processes around AI, you're not alone. However, a better approach is thinking of AI as a tool to improve your existing processes. 

For example, instead of using AI to increase the volume of your prospecting emails, you can use it as a research tool to better understand each prospect and write more impactful messages.

And remember, balance is key. The best AI systems will be those that empower sales professionals to do more without losing the personal connection at the core of sales.

3. Longer Sales Cycles

In 2023, more than a third (35%) of US consumers planned to make fewer purchases due to a possible recession — and we predict this trend will carry over into 2024.

When wallets get tighter, sales cycles get longer. Consumers need more time to make purchasing decisions, and they tend to lobby more objections throughout the process.

How to Handle This Challenge

Focus your energy on engaging with prospects with the highest likelihood to convert, rather than spreading yourself thin over numerous leads. By intensifying your interactions with these leads, you'll use your time more effectively and enhance your prospects of closing a sale.

Additionally, consider offering flexible pricing plans. Among sales reps who offer freemium options, a staggering 90% say it's "very effective" at turning prospects into paying customers.

Dan Tyre echoes this point, telling me, "Offering a free tool or widget, product trial, consultation, or services checklist can increase your visibility early in the sales process."

4. Marketing/Sales Misalignment

There's a reason why 1 in 4 sales reps report that improving marketing/sales alignment would result in the most growth for their company.

When this alignment is fragmented, both sales and marketing teams suffer. Marketing teams are unable to effectively generate and pass on high-quality leads, tailor content to the specific stages of the buyer's journey, or get the feedback they need to refine their strategies.

Sales teams, on the other hand, are unable to leverage insights from marketing to fully understand the customer's needs, waste time chasing poor-quality leads, or capitalize on the full potential of the marketing materials and campaigns.

How to Handle This Challenge

A good customer relationship management (CRM) system is a central part of aligning sales and marketing teams. In fact, 78% of sales professionals say their CRM is effective at improving sales and marketing alignment. Additionally, sales professionals who use a CRM are 79% more likely to say their teams are strongly aligned.

For example, HubSpot's Sales Hub offers a wide range of tools — including lead scoring, email templates, and a high-powered analytics dashboard — to help increase alignment and collaboration between marketing and sales.

Try HubSpot's Sales Hub for Free

5. Realizing a Solid Product Alone Won't Close Deals

Manos also asserted that sales reps won't be able to rely primarily on how sound their product or service is to land deals. According to him, "The quality of the technology you're selling alone doesn't close big deals."

Touting your solution's bells and whistles and technical performance is less effective in the "seas of same" that characterize the competitive landscape of most modern industries — particularly SaaS. In 2024, there needs to be much more to your efforts.

How to Handle This Challenge

According to Manos "With the sheer number of competitors offering any specific SaaS solution, running a strong sales process is more important than ever. When sales reps push for a close, without having executive buy-in and a clear ROI, more deals will be lost to 'no decision' and timelines will push."

6. Moving Towards a Buyer-First Mentality

According to Kwesi Graves, VP of Sales at Scribe, prioritizing buyer interests will have more bearing on how reps conduct their sales efforts, going forward. He says, "When we think about the concept of buyer-first, it's redefining the paradigm.

"We're going to look at how buyers want to buy versus how we choose to sell to them. It's all about mindset and scrapping out or wiping the hard drive from that old mindset, especially in the way we're selling now in this market."

How to Handle This Challenge

Adopting a more consultative, helpful, empathetic approach to selling is the key to handling this challenge — taking steps like listening actively and having conversations tailored to getting at the "why" behind a sale will be key, going forward.

Sales efforts can't be presentation-first anymore. You need to avoid "talking at" your prospects if you want to adapt to a buyer-first landscape. Emphasis has to be put on elements like extensive buyer research and relationship-building to adjust to a world where the buyer has the power.

Familiarize yourself with concepts like customer-centric selling. Learn how to conduct your sales efforts without pressuring buyers. Try to plan your efforts around your prospects' timelines as opposed to your ideal schedule.

One way or another, acquaint yourself with your buyers' unique challenges and put them first. Strides like the ones listed here provide the best avenues for you to better understand and adjust to a world where the buyer has a disproportionate amount of power in the prospect-salesperson dynamic.

7. Incorporating Social Selling Into Their Broader Efforts

Social media is more or less omnipresent in virtually every aspect of modern life — and the sales world is no exception. Social selling skills are becoming much more of a "need to have" than a "nice to have" for sales professionals.

According to data from LinkedIn, 78% of social sellers outsell peers who don’t use social media. 

How to Handle This Challenge

Salespeople need to have a grip on how to leverage platforms like LinkedIn and Twitter for processes like prospecting, sharing relevant content, seeking referrals, and developing clout in their spaces.

This challenge isn't necessarily new, but it's as pressing as it has ever been. Every salesperson needs to account for the rising tide of digital transformation. Social media, as a sales resource, isn't going anywhere — so it's in your best interest to incorporate it into your repertoire if you haven't already.

8. Selling to Buyer Groups as Opposed to Just Buyers

Gone are the days of appealing to individual buyers. According to research from Forrester, 63% of purchases have more than four people involved — up from just 47% in 2017. These buyer groups typically involve prospects with varying degrees of authority and influence.

The people you engage with when selling to a business can include gatekeepers, influencers, blockers, champions, users, decision-makers, and a host of other representatives that can make or break your deal.

How to Handle This Challenge

Thorough research and personalization are central to overcoming this challenge. You need to be prepared to connect with all of the types of contacts listed in the previous paragraph — a process that's much easier said than done.

At the end of the day, those contacts are individuals, so naturally, they're going to be receptive to an individualized approach. Research the prospects you talk to — and get a feel for their priorities, personal inclinations, and level of seniority at their companies.

Along with that, understand the common denominator that connects them — the business they work for. Know its ins and outs. Understand its industry and where it stands relative to its competition. Have a feel for its pain points, and be able to speak to all of those elements when talking with anyone you connect with from it.

9. Standing Out From the Competition

According to HubSpot's recent survey of over 1,000 sales professionals, standing out from the competition was one of the most prevalent challenges facing salespeople — with 26% of respondents citing it as a major issue.

Differentiation is a key issue across virtually every field, and sales is no exception. Salespeople are some of the most important agents when it comes to setting their companies apart from their competitors.

Businesses distinguish themselves with their specific value — and at its core, sales is the process of conveying that value as effectively as possible. And if your industry is flooded with a variety of options that all serve the same fundamental purpose, that process can get complicated and frustrating.

How to Handle This Challenge

Overcoming this challenge starts with determining value through understanding — having a thorough pulse on how your product or service works, the vertical you operate in, your buyer personas, who your direct competitors are, and how they try to set themselves apart.

Obviously, that's a lot to keep tabs on, and developing that kind of knowledge is easier said than done — but you need all of that if you're going to craft an effective value proposition. Know your offering's features and the benefits that stem from them, inside and out.

Thoroughly research the businesses in the space you serve to identify common pain points. Talk to your existing customers about why they chose your solution. Put together a solid picture of the typical prospect who might buy from you, and adjust it as your landscape changes.

Understand your competitors as best you can. What do they offer that you don't? Where are you stronger? Where are you weaker? Do you have features they don't? Do you charge at a more accessible price point?

The unique value your company can offer provides the basis for your differentiation. If you want to stand out from the competition, you need to know what makes your business special — if you can get there and sell on that basis, you'll be in a solid position to stand out from your competition.

10. Keeping Prospects Engaged Throughout Their Sales Processes

17% of our survey's respondents said keeping prospects engaged is a major challenge. And that makes sense, your sales efforts can only go as far as your sales process permits — even the best salesperson can be limited by a lackluster one.

And though that trend is troubling, it's a fact of sales life — and if you want to get the most out of your efforts, you need to know how to keep your prospects intrigued and enthusiastic throughout the process's entirety.

How to Handle This Challenge

Approaching this challenge falls on both sales leadership and the individual reps they oversee. It starts with leadership putting together a sales process that lends itself to engagement — ones that strike a balance between thorough communication and timeliness.

Next, the reps who leverage the process need to execute it effectively — specifically when it comes to communication and building rapport. You, as a salesperson, need to quickly develop and sustain trust with prospects.

That means communicating with them throughout the sales process — finding ways to convey value at every stage with the parties you engage with. Touch base consistently but not intrusively. Research the companies you sell to and the contacts you get in touch with, and shape your conversations around what you find out.

Let your prospects know you're there without being overly eager or obnoxious. As I said, engagement stems from tactful, effective communication. Learn how to keep them aware without annoying them.

Back to You

So long as sales reps and managers demonstrate persistence, adaptability, and a constant commitment to solving for the customer, they should be able to handle the challenges of the new sales landscape.