Picture this: Jenny, a seasoned sales rep at a mid-sized tech company spends hours and hours each day scouring potential leads. Yet, she ends up contacting prospects who either gave no need for the product or lack the authority to make purchasing decisions. 

Just like Jenny, many sales reps struggle with similar challenges—identifying the right prospects, personalizing the outreach and building rapport. 

In this article, we'll talk about the exact challenges most sales reps face, so you don't have to. So, keep reading.

Challenges of sales prospecting

Let's understand the different sales prospecting challenges you might struggle with:

Challenge 1: Finding the right ICP

Sopro’s research highlights that 19% of sales and marketing decision makers are unable to build systems that bring in a steady stream of high quality leads. Ending up talking to low quality leads has remained as one of the top challenges for sales reps since 2023.  And when sales reps spend their time reaching out to such leads, they'll end up wasting most of their time and resources. 

Ideally, these leads will have the following traits:

• Poor audience demographic & product fit
• A misunderstood perception of the solution you're offering
• Lower influence on decision-making power
• Smaller budgets
• Lack of immediate motivation to buy the product

So, what's the solution? Find the right ICPs. 

How, you ask?

Leverage sales intelligence tools to look at trends, patterns and common themes among firmographic and behavioral data. Based on this data, you can create an ideal customer persona you'd like to reach out to.

If your company sells a project management tool for instance, you need to target project managers, project marketing teams. Here's what you'll look for:

Firmographic data:

• Industry: B2B SaaS
• Location: USA & UK
• Company size: 50-1000+ employees
• Revenue: $10M-$500M+

Behavioral data: 

• Project complexity: Manages multiple large-scale projects
• Engagement: Regularly attends webinars and downloads industry reports
• Tech savviness: Early adopter of new tools 

Technographic data:

• Current tech stack: Jira and Trello
• Integration: Integrates with CRM tools

To build such comprehensive ICP lists, use tools like Happysales. All you have to do is integrate your LinkedIn profile with Happysales. You'll then get insights like the prospect’s personality insights, pain points, etc. Based on these insights, you can build and refine your existing ICP list.

Challenge 2: Spending too much time on prospect research and outreach

Did you know sales reps spend 9.3% of their time researching prospects—which is the third major activity reps spend their time on after prioritizing leads and meeting in person with customers? 

First, reps spend most of their time researching the prospect. Once they’re done with their research, they spend another extra hour perfecting their outreach:

“What icebreaker to use in the email or when the prospect takes the call?”

“What would be the right subject line that gets prospects to open the emails?”

“What CTAs should I use to get the prospect to respond to the email?”

“How to keep the conversation interesting for the prospect not to disconnect the call?”

“How to write a personalized email for each prospect without making it appeal as spammy and something that’s sent to the masses?”

Spending time understanding all these questions and perfecting the pitch adds a lot more to the rep’s responsibilities. In the end, sales reps only spend 28% of their time actively selling. 

The solution? Using AI sales prospecting tools to speed up your research. With AI sales prospecting tools, you can identify pain points relevant to specific persona, generate icebreakers and craft cold emails and messages unique for each prospect.

Doing so, reps can save 2 hours a day on prospect research. 

Happysales, for instance, integrates with LinkedIn and analyzes the prospect's LinkedIn profile to do the following:

• Give insights on prospects’ personality and their pain points
• Auto-generate icebreakers and pitch
• Tailored messaging recommendations

Based on this information, reps can craft unique and personalized emails for multiple prospects and send personalized emails in masses. 

In case they’re reaching out to the prospect via cold calls, Happysales generates the talking points and the script based on the prospect’s LinkedIn profile—eliminating their anxiousness about getting rejected by the prospect. 

Challenge 3: Building trust and establishing credibility

It's hard for prospects to trust sales reps. Here's why:

• They believe reps would pressure them into making a decision that benefits the reps more than the prospect themselves.
• Reps start bombarding them with sale-sy offers.
• They feel sales reps are not genuinely interested in offering the right solution but in hitting their own sales targets. 
• You haven't built rapport with the prospect before reaching out to them. 

All of this brings a question mark on your credibility leading the prospects not to trust you. 

So, what should you do to instill trust in them? 

First, leverage social selling. Instead of directly reaching out via email or cold calls, engage with them on their preferred social channels. 

For example, find them on LinkedIn, send them a connection request, and engage with them—either by commenting on posts on their company page or on the posts they share (if they do). Keep the hard selling strategy for email outreach and calls. 

Next, leverage consultative selling. Dig deeper and identify the prospect's pain points, how are the specific problems increasing friction in their workflow, and identify ways your solution can reduce that friction. Make sure to offer your solution only if the prospect *really* needs it and not just for the sake of selling the product. When you do this, prospects find you more authentic and trust you more. 

Challenge 4: Struggling to fill the pipeline with enough meetings

Picture this: your sales team has been sending out cold emails, conducting cold calls, and following these prospects on social media. Yet, the reps haven’t heard back from them. 

Result? No new meetings booked. No new leads in the pipeline. 

Do you know why this happens? Because:

• Reps are juggling between multiple tasks—following up with the prospects, crafting a personalized pitch, and other administrative tasks—leaving them with limited time for prospecting and adding new leads to the pipeline.
• Reps rely on outdated prospecting strategies, leading to a lower response rate. For example, sending generic, mass email blasts to prospects. 
• Reps are inconsistent with their followups.This is usually due to lack of time or reps find it daunting to do multiple follow-ups with a specific prospect.
• Reps haven’t been trained well, which leads to them missing out on closing the right opportunities.  

To change your situation and  fill your pipeline with enough meetings: identify the gaps in your sales pipeline. 

If the reps are inconsistent with their follow-ups

Use automation tools to speed up the process. For example, use email marketing software like Lemlist to automate your follow-ups. 

If the sales rep needs coaching

• If the reps are reaching out to prospects via social channels and email, check their messaging, CTAs, subject lines used, and whether the emails are generic or personalized.

• If they’re reaching out to prospects through cold calls, record the calls using AI sales intelligence software like OpenPhone, get call summaries and transcripts to navigate the calls quickly and give feedback to the sales reps. 

💡Pro tip: Use AI sales coaching tools like Happysales to emulate prospect behavior by analyzing real prospect information using LinkedIn data, internet-scale information, and DISC personality assessment. Reps can roleplay with the AI prospect and get feedback in real-time. Reps can also use the “AI sales coach” feature to pause the role-play and get guidance in real-time sales.

Once the rep has completed the AI roleplay, they'll receive instant feedback on the rep's talking speed, tone of voice, pain points highlighted, and so on. This helps the rep understand the key areas they could improve on when pitching the prospect in real-time.

Challenge 5: Lack of personalization

Are your sales reps bombarding the prospects with mass emails? Are they sending the same copy-paste email to every prospect they’re reaching out to? Mass outreach without personalization is the sure-shot way to lose the prospect—even without your first interaction with them. Why? Because they are never going to open your emails or pick up your calls.

It’s 2024, and sales prospecting strategies that used to work years back have changed entirely. Today, if you want to get eyeballs of prospects on your solution and get on a sales call with them, you need to leverage personalization  to your cold outreach—whether you’re sending cold emails, interacting with them on social media, or doing cold calls. 

In fact, buyers who receive personalized emails are 23% more likely to open the emails. Clearly, personalization is the winner. So, when connecting with prospects and leveraging cold outreach campaigns, personalize your messaging. 

Here are a few ways you can do so:

• Personalize your email subject lines 
• Personalize with individual-level icebreakers
• Highlight the prospect’s pain points
• Mention the technologies they use
• Mention their relevant social media activity

For example, you're selling a demo automation tool, and it integrates with Salesforce. If the prospective company is using Salesforce in their workflow, highlight in your email how your product integrates with the tool they're already using—making their workflow seamless. 

However, sending such hyper-personalization requires you to spend long hours. And when you want to execute cold outreach campaigns at scale, sending such targeted messages is difficult.

Solution? Use AI sales tools to personalize and send emails in bulk. With Happysales’s bulk personalization feature, you get 100+ intelligence triggers to personalize your emails and send them at scale. 

Happysales—the boon to your sales prospecting struggles

If you want to win over your fears with sales prospecting, AI is your savior. It not only saves you time but makes your processes more efficient. 

With Gen AI in sales tools like Happysales, you can:

• Integrate the tool with LinkedIn and get insights on prospect’s personality and pain points
• Generate automated icebreakers and email copies with AI-based analysis of real prospect instead of generic info
• Get real-time feedback to improve your sales pitch with AI sales coaching for better conversions

Curious to see how Happysales can take personalization to a whole new level for you?

Check it out here.