15 Sales Challenges Facing Sales Reps

Written by
Luke Marthinusen

These days, the power to close a deal has more to do with the prospective buyer than it has to do with a sales rep’s ability. With technology at their fingertips, buyers are more informed than ever.

They can research the company, products and even the salespeople before making a decision. They can compare your offering against all of your competitors, are well informed on what will work for them, and simply won’t be sold over a cold call.

So how do you tap into this dynamic to close more? Read on.


The changing sales landscape

In truth, consumers will usually decide how they’re going to spend their hard-earned cash before they even meet with a sales rep.

In all likelihood, your prospect has narrowed down their choices to two or three select vendors before they make contact.

As Inbound Marketing evolves, successful salespeople are starting to move away from old hard-sell tactics and shift into a 'trusted advisor' role.

To keep up with shifting consumer sentiments, which are now heavily influenced by technology, sales reps need to connect with customers on their preferred channels. And they need to be authentic and helpful in their messaging and approach.

Organisations need to incorporate these changing sentiments into their Sales Strategy.

15 Sales challenges facing Sales Reps

1. Building trust online
2. Marketing and sales teams integration
3. Getting a response from prospects
4. Closing deals
5. Prospecting good leads
6. Engaging multiple decision-makers at a company
7. Avoiding discounting
8. Connecting via the phone (getting in touch)
9. Incorporating Social Media into the sales process
10. CRM systems
11. Establishing urgency
12. Overcoming price objections
13. Lead management
14. Qualifying
15. Nurturing leads that aren’t ready
16. Upelling and return business

These are the top challenges faced by sales reps:

1. Building trust online

In the wake of the Covid-19 global pandemic and social distancing protocols, most sales reps are now making use of emails and phone calls as their dominant form of communication with their prospects. This comes with its own set of challenges, as standing out from all the other emails and calls prospective customers receive is no mean feat. Establishing credibility with a virtual barrier between you and your prospects requires new techniques to differentiate you from your competitors.

Solution: This can be achieved through personalised interactions. Having someone behind the sales interaction whom the prospect can relate to and connect with, in a ‘human’ way is crucial. It is also important to ensure that your efforts are relevant, timely and on the right platform so that you can meet the prospect on their terms.

2. Marketing and sales teams integration

Sales and marketing traditionally work in silos, which can negatively affect lead management and, ultimately, your ability to close deals. When marketing and sales are working in different systems and managing data separately, duplication and loss of data is almost guaranteed to occur.

Solution: Combatting this requires sales and marketing teams to break down the walls of tradition and work together as an integrated system of goals and processes. This can be achieved by creating a central hub of truth (consolidated, consistent data) that integrates both teams and the leads/prospects they are working on.

3. Getting a response from prospects

Sales reps tend to agree that the most common challenge they face is getting a response from prospects. Despite all the devices that we have on hand, and all the communication technology available, consumers are less responsive than ever before. This may be due to a proliferation of channels or simply, information overload.

no response

Sales reps need to distinguish their voices from the crowd and become trusted consultants that their customers can rely on.

Solution:  Use video to differentiate yourself. When you reach out to a lead, do it with a video in your email. This is called 'video prospecting'. Solutions like HubSpot, Loom, and Vidyard allow you to do this. 

4. Closing deals

Closing a deal is the second most challenging aspect of sales. Globally people are facing challenging economic times and, in a market that is increasingly competitive, consumers don’t want to feel pushed into buying.

closing deals

Instead, consumers, today prefer to do the legwork themselves. With tools like search engines readily available, acquiring expert knowledge on a company, product or service (and even the sales rep!) is an easy task.

The salesperson needs to become intimately familiar with the challenges that their prospect faces, and customise a solution targeted to that person's needs.

Solution: What question are your prospects always asking you? We all have that one question that we all get asked, and we know how to answer it perfectly. Write the answer into a blog, or have someone ask you the question and make a video of you answering it. A smartphone is all you need to do this. Get the content up on your company blog, and share it like crazy on your social channels – especially LinkedIn. You can share it again every month! Don't be shy.

5. Prospecting good leads

Quality leads are becoming harder and harder to find. One of the main complaints we hear from sales folk, is that the leads they get from their business are really poor quality.

Engaging with brands and companies is easy for consumers to do, but how do salespeople separate the wheat from the chaff? The answer lies in the alignment of marketing and sales with an SLA between the teams.

sales and marketing sla

Aligning marketing and sales teams with an SLA can assist in qualifying quality leads before they are passed onto sales by using a solid CRM that can automatically score leads, plugs into LinkedIn for prospect intel, and will only pass on leads that are ready to buy now.

An SLA also works the other way with the sales team regularly giving the marketing team details on which leads were good so they can generate more of them.

Solution: Send the marketing team a daily report with the progress of leads they pass on. Make the report easy to understand. They'll send you more leads if they know you are following up with them. They'll also send YOU the good leads. Marketing teams are desperate for feedback on their leads, and quick follow up. It makes them look good when they report at month-end. Agree to a regular feedback schedule (SLA) with the marketing team. They'll be blown away.

6. Engaging multiple decision-makers at a company

Salespeople strive for in-company connections to be 3-wide and 3-deep. What this means is that at the face of the company, a salesperson should have at least three contacts, and these contacts should be able to open an inroad into the business three levels deep, toward the key decision-makers.

selling to decision makers

Engaging multiple decision-makers and influencers is increasingly challenging for salespeople and can be solved by creating useful content that is targeted towards the organisation, and the various personas in that organisation (decision-makers and influencers), which then becomes easily shareable among colleagues.

Solution: Remember the question you get asked all the time? Expand it out now, put it on a letterhead and put the title 'Special Report' on it.

Add two new sections. One for the decision-makers (maybe the CEO, CFO, Head of XYZ...) and the other for the influencers (maybe the IT manager, administrator, or accountant...).

Answer the question in the way you’d explain it to them if you were sitting in front of that persona. PDF it and send this to your contacts at the prospect. 'I wrote this, I thought you might find it useful in your decision-making process.' If it works well, ask the marketing department to design it into a proper branded sales document.

7. Avoiding discounting

No business wants to enter a price war, it is always a race to the bottom and no one wins. In order to bring in new business, salespeople might consider negotiating on their pricing, but this ultimately becomes a client expectation and there is no back-pedalling.


Sales reps should consider adding value, instead of discounting on price as a solution to finding an accord with new business prospects.

Solution: You've added value during the sales process with the PDF above. Now look for something that you know you can deliver at a very low cost. It must be something the prospect will find very helpful and your competition will not think to throw into the deal or maybe just can't. I often throw in an SEO audit when we are closing a new CRM deal. My clients love this. 

8. Connecting via the phone (getting in touch)

Our mobile devices have become an integral part of our daily lives, so how is it that salespeople are finding it more and more difficult to reach people on the phone? It is true that with so many means of communicating, often people prefer to email or text over having a conversation on the phone. People's busy schedules also make them more difficult to reach.

sales call-1

Salespeople can consider alternative means to communicating which don't require two people to be available at the same time. But I still think talking on the phone is critical in the sales process. So much is said in between the purpose of a call. So many little cues that can enhance your deal probabilities. 

Solution: Using a platform like HubSpot CRM, you tag your emails so that when a prospect opens up your email or quote you can call them to follow up. They will more than likely answer, as you're not interrupting another task, meeting or process. This makes connecting more relevant. Also, if a sale goes dead, and they open up your quote six months on - you have a live one...

9. Incorporating Social Media into the sales process

A major challenge for sales reps today is understanding how to use social media tools in the selling process. It comes down to understanding where your leads are and connecting with them on their preferred channels.

social selling 1

Sales should work with the marketing teams to understand where customers are handing out online and identify the best fit for business strategies to connect with their audience. Marketing can then use relevant social channels like the B2B network – LinkedIn to locate and target the best prospects.

Solution: Sponsored LinkedIn InMail campaigns is an incredibly powerful tool for targeting new prospects in very specific industries and locations. If you haven't got the technical skills or the marketing team that can execute on this, one-on-one InMails are a good alternative even if this is a little more time-consuming.

10. CRM systems

Sales teams tend to only see CRM’s as extra admin that slows them down and provides minimal benefits. This is not the case. CRM’s are designed to aid sales reps in their efforts and reduce the time they spend on admin so they have more to spend talking to prospects.

Solution: It’s all down to the correct implementation and alignment of the CRM to the sales reps that are going to be using it and the processes they follow. When done correctly, a CRM will be an invaluable asset for sales reps to close more deals and manage more leads effectively and efficiently.

11. Establishing urgency

Prospects buy on their own time, this does not align with sales team targets and the urgency they feel to close.

Solution: Giving your prospects a deal value deadline or explaining the time required to launch their project can help motivate your prospects to sign.

12. Overcoming price objections

Presenting the price to prospects can either be as simple as being featured on your website or needing to be a full discussion with the prospect. The latter becomes complex when the prospect is comparing you to your competitor’s pricing or their perceived value is low.

Solution: Elevate the prospect’s perceived value to the actual value they will be provided at that cost. As long as you’re addressing the real problem they are facing, the value will speak for itself. Ask yourself, is the service or product actually solving their need or is it just something they showed interest in and are now pushing on them to buy?

Understanding your competitors and the market pricing is essential. Are you overpriced or is the quality and value you are providing worth more? Do you need to drop your pricing to create value for entry-level products and services that will bring in more revenue from their upsells and return business?

13. Lead management

Depending on the success of running marketing campaigns, sales teams can quickly get overwhelmed with leads in all stages of the buyer’s journey.

Solution: With a CRM in place, leads can be segmented by their position in the buyers journey and help marketing qualify leads so sales teams only work on the leads that are ready to be contacted. Through a CRM, a process can be developed so leads and prospects are qualified, nurtured and contacted when and how they want.

14. Qualifying Leads

As mentioned, sales teams wasting time on unqualified leads costs money it’s important to focus on the right leads that come through the funnel and at the right time.

Using the solid criteria for sales and marketing leads is integral to an effective sales enablement strategy.

Solution: If your company has the right personas in place, you can easily reference them when qualifying your prospects.
The basis on which you qualify your prospects can be broken down into the following aspects:

  1. Customer profiling: Do they fit into your determined personas?
  2. Their needs: Understanding their leads and if and how your solution will help them.
  3. The decision-making process: Who is the key buyer, and how many people are involved in this process?
  4. Your competition: How many competitors does your business have, and how do your offerings differ from theirs?
  5. Is their business within your defined target location?

15. Nurturing leads at the right time

It’s easy to send out emails and make calls to a prospect list, but the time you make contact with them can make or break a relationship. Analysing each prospect is time-consuming and full of gaps without proper activity tracking in place.

Solution: With a CRM in place, sales teams can set up scheduled reminders for themselves to assess a prospect after certain actions take place. Actions can also trigger automations that send emails to prospects at set intervals. These activities can range from visits to certain pages on your website to opens and clicks of your automated and outreach emails.


Upselling and return business

After a deal is closed, it’s easy to move your customer out of mind while you focus on new business. Remember, though, that every first-time buyer presents upsell opportunities that should not be wasted.

These clients can be automatically added to nurture campaigns that keep your business top of mind and educated on your other services and offerings. With a CRM, sales teams can be reminded of clients’ regular events and purchase habits to reach out to them pre-emptively rather than reactively.

Final thoughts

These challenges faced by salespeople can be addressed with a modern sales strategy, shifting the way you communicate and do business. A modern sales strategy helps marketers and sales managers make better decisions about their outreach and conversion tactics while bringing both departments together to achieve their shared goals.

We've put together a guide to building your own modern sales strategy so you can start addressing the sales challenges you are facing. 


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