Why is Prospecting Important: 6 Tips for Reaching the Decision-Maker


Jennifer Groese CMO at Winmo

Friday, April 12, 2019

Getting through to the decision-maker is the main objective of any sales person. But there are often a number of obstacles when it comes to making that connection. Here's some top tips to help.

Article 8 Minutes
Why is Prospecting Important: 6 Tips for Reaching

With so many competitors flooding your prospect’s inbox, getting through to the decision-maker today is harder than ever. With on average only 9% of sales emails being opened, how are you supposed to make a buyer stop and pay attention to what you have to say? 

Before jumping into the “how”, it’s important to understand the “why” behind prospecting.

Why prospecting is important 

Prospecting is a critical piece of growing your business. This helps build a pipeline of potential leads that you’re then able to convert into customers and - later - advocates for your brand. Some companies sit back and wait for opportunities to come to them, however, the most successful sales teams are proactive and go out to find new business themselves. 

While prospecting is important it’s only one piece of the sales cycle. Knowing who you’re targeting, developing the right sales messaging and leveraging the right outreach channels are all required as well. 

When trying to capture the attention of the decision-maker, or get around the gatekeeper, here are six tips I recommend.     

1. Invest in the right tools 

When trying to connect with the decision-maker, you first need to ensure you’ve got the right tools in place. With 9 out of 10 companies using two or more lead enrichment tools to more effectively connect with their prospects, it’s crucial you have the proper resources connected and working together. 

When looking for the right decision-makers, on the right accounts, at the right time, here are a few must-have technologies to consider:

Sales intelligence platforms

Sales intelligence technologies can help sales teams work faster and more efficiently by building targeted lead lists and capturing accurate data on all the stakeholders at each account. Additionally, most tools allow you to set up alerts and track relevant company changes so you can identify sales opportunities as they’re happening. 

Great examples include Winmo, LeadGenius, and LinkedIn Sales Navigator. 

Customer relationship management (CRM)

Your CRM is one of the most important tools you’ll invest in. The CRM manages all of your company’s relationships and interactions with current and potential clients, allowing you to streamline processes and improve profitability. Leverage this technology to store important decision-maker data on each account, track their activities and even add them to targeted campaigns.

A few recommended CRM’s include Salesforce, Airtable, Hubspot, and Pipedriver. 

Sales email automation

Sales requires many manual tasks. So many, in fact, that Inside Sales found that only 35.2% of sales reps’ time is actually spent on selling the product. The rest of their day is spent on administrative tasks, research, and other non-selling obligations. 

Luckily, sales automation tools help you connect and convert more decision-makers while reducing manual processes such as:

  • Logging activities and updating lead records in the CRM
  • Looking up prospects contact information
  • Setting reminders for phone calls after certain emails are sent
  • Emailing content to prospects based on where they are in the buyer’s journey

Examples include Salesloft, Nutshell, and Click-to-Call.

2. Catch their attention

On average, it takes 18 phone calls before sales professionals connect to a decision-maker. It’s important that when you do get ahold of them, you spark interest immediately.

Too many sales professionals have the same style. They give decision-makers a call and want to chat about how they can help. I recommend taking a more personalized approach to your outreach. In sales, there is no “one size fits all” message. If you really want to capture their attention, you’ll need to do some research on who you're connecting with. 

Personalized emails get 14% more click-throughs and six times as many transactions. Here are a few suggestions for making your outreach more personalized:

  • Use a personalization token (insert their name) in the email preview text
  • Reference 1st or 2nd-degree connections you share on LinkedIn
  • Write a clever subject line
  • Utilize public information to call out specific company figures
  • Scope out your prospects’ personality traits to speak their language

3. Don’t blow off the gatekeeper

More often than not, you’re going to speak with the secretary or executive assistant before actually getting through to a decision-maker. One of the biggest mistakes sales professionals make is to overlook the opportunity here. Gatekeepers decide which calls go through and which packages get left on the desk. The gatekeeper essentially rules your prospect's world so don’t try to get around them, try to win them over.

Consider the secretary or executive assistant as your first sell. If he or she thinks you’re offering value, they’ll take it to their boss and make a case for you. But before this can happen, you’ll need them to trust you.

You have about six seconds before the EA will decide if they’re going to hear you out or not. Don’t lead in with your sales pitch or they’ll quickly tune you out.

As an example, let’s say you‘re trying to set up a meeting between your boss and the decision-maker. Here’s what your six seconds should sound like:

“Gina, Hi. This is Jennifer. I work for Joe Smith, the CEO of X Company and he asked me to call and see if Bob is available for coffee next week.”

Keep in mind that as you begin prospecting larger companies, you’ll find that getting past the gatekeeper can be much more challenging. Listen to what they have to say, be polite, and try using other avenues to connect with the decision-maker. For example, gatekeepers typically don’t monitor their boss’s personal social media accounts so try shooting over a personalized LinkedIn message there as well.

4.  Be conversational

While reaching out to decision-makers, you won’t see much success if the conversation revolves around the details of your product. Instead, change the conversation to build rapport as the more information you have about their challenges, the more likely you are to provide solutions.

Ask the prospect thought-provoking questions that make them think about their business and where their gaps are. Here are some example questions:

  • What kind of problems are keeping you and your team from reaching your goals?
  • What are your goals for the next 6 months?
  • How does your company evaluate new products or services before buying?
  • Are you having problems with [insert pain points]?
  • If [pain points] were handled more effectively, what kind of impact would it have on your revenue/workflow?

When they realize they don’t have an answer to your question, they’ll begin to see that there might be a need for your product or service. By making them stop and think, you’ll stand out against the competition. Prospects will also feel more comfortable when they realize that not only do you have a deep understanding of their problems, but you’re able to bring actionable solutions to the table as well.

5. Think quick on your feet

Decision-makers like to ask the tough questions so be ready to roll with the punches and maintain your composure. Often times, executives do this to see how confident you are in your answer. Stay calm throughout the conversation and never give up control.

Additionally, don’t give up after getting an objection. Just because someone is pushing back, doesn’t mean they’re rejecting you. You still have time to change their mind but you must have a response ready to go.

According to Sales Gravy, when it comes to responding to objections, follow these three tips:

  1. Prepare - When you hear an objection, your brain will instantly go into panic mode so it’s important that you have a script prepared and ready to reference if needed.
  2. Disrupt - Say something different to everyone else or they won’t hear you. Disrupt the pattern that they normally hear to make them stop and think. For example, If they say “I’m busy” reply with, “That’s exactly why I called! I wanted to schedule a time that was more convenient for you to have a chat. When might be the best time to give you a call?” They won’t be expecting you to say “that’s why I called” and it will surely catch their attention. 
  3. Ask - Ask for exactly what you want whether that be scheduling a call at a better time, setting up a demo, or meeting in person.

Keep in mind that roughly 80% of prospects will say “no” four times before they’ll say “yes.” Each conversation will take a different approach however if you’re consistent in the framework of the conversations you’re driving, you’ll quickly see success. One thing is for sure, if you don’t try, you won’t win.

6. Don’t be afraid to follow up

Studies show that 48% of salespeople never follow up with their prospects. Other studies show that 50% of sales happen after the fifth outreach. You can’t be afraid to follow up with decision-makers. Their inboxes are crowded and their voicemails are full so you need to break through the noise and it will take multiple attempts before you get noticed.

Don’t just do the casual “just checking in” follow-ups either as they’re entirely too vague. Use your follow-ups as a way to spark interest and identify your prospect’s pain points. Also, try different avenues for delivering your follow-up. If your first email doesn’t get a response, try sending a video message via email.

Once again, something different that they aren’t expecting will typically get a better response.

Jennifer Groese

Jennifer Groese is the CMO at Winmo and currently oversees all marketing operations, including customer acquisition, product adoption and advocacy, and retention and experience.


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