The Strategies That Can Make — or Break — Your Sales Prospecting

April 14, 2020

“With everything going on in the world, it’s critical to lead with empathy first,” said Matt Deis, director of sales at IT company Electric.

 When prospecting, Deis advises reps to “humanize themselves,” then provide specific examples of ways they can help organizations like the one they’re reaching out to.

Now is not the time for pre-templated, blanket emails.

“People need relevant, actionable insights, and if you don’t have them, you’re not going to get the engagement you’re looking for,” Deis added. Now is the time to get personal. 

Rather than depending on metrics like call volume for success, Whitney Hudson, director at customer data platform Simon Data, said reps need to focus on how they can add value to a prospect’s role or business. To find the answer, Hudson recommends spending time on the company website and their company profile on LinkedIn.

“Prospecting is the key to how sales reps can control their own success,” Hudson said.

Let prospects tell you what their needs are, and offer a solution through your company’s product, Hudson advised. “Listen and learn” is even one of her company’s core values.

While prospect research yields higher success rates, it’s still just as important to practice the pitch. Justin Gurss, account executive at customer experience platform AB Tasty, said new sales reps should spend an entire day prospecting and pitching to as many companies as possible. Repetition allows reps to mentally prepare for and overcome the fear of rejection, develop answers for every kind of objection, and practice and perfect the business pitch with confidence.  

“The idea is that you’re going to fail, and that’s okay,” Gurss said.

 

Cristián Enríquez
Sales Manager, Strategic Corporate Accounts

Never underestimate the power of a personalized message, Remesh Sales Manager Cristián Enríquez said. Using the prospect’s same language style, which can be found on LinkedIn, creates a sense of familiarity, even with a cold pitch. 

 

When it comes to prospecting, what actions have you found to be critical to success?

Covering the basics is fundamental to ensure success. I send a message that is as personalized as possible, use the same language as the prospect (which you can get a sense of from LinkedIn), and focus on creating a message that bridges their overall needs to what we can offer. To do this, I spend quite some time doing desktop research on my prospects and their organizations so that I know my offering is relevant to both the organization as well as the role that I am reaching out to. 

When available for  public companies, I also go over financial statements. This is a great way to uncover what is important from the top down and find what is driving the organization forward. 

 

What’s an underrated technique or strategy that youve found to be really effective in sales prospecting? 

Listening to call recordings is underrated because people don’t feel comfortable doing so. We are looking into technologies that would provide us with a full suite for call recording and analysis. It is a great way to improve and conduct training. An additional strategy is A/B messaging testing because we need to try different approaches for different buying personas. For A/B testing and additional metrics, we use Outreach.

Covering the basics is fundamental to ensure success.”

 

What’s an overrated technique or strategy that youve found to actually be ineffective?

Relying too much on buying personas. I think having those are great guidelines, but more often than not, sales professionals see this as a rule to follow. We need to make sure that we are going after the right role and person and this requires doing a little more research because in today’s world, similar companies in the same industries have different titles and different people fulfilling various roles. We as salespeople have to be careful about stigmatizing a role and creating a buyer persona that does not represent the actual buyer.

 

Whitney Hudson
Director of Client Development

Sales templates are only the starting point for Hudson, not the standard. Instead of focusing on data metrics like call volume, she said a personalized approach with each new prospect yields higher success rates. A personalized approach works for her team as well. Each sales rep receives individual quarterly goals, and is told to work backward to estimate how many new opportunities they need to create in the quarter to hit that goal. From there, they’re given the autonomy to manage their own schedules and do what they need to do to hit goals. 

 

When it comes to prospecting, what actions have you found to be critical to success?

Prospecting is the key to how sales reps can control their own success. Often I find that one of the main attributes that differentiates a star performer is their willingness to consistently prospect. It’s not always easy, especially when you’re balancing active deals, but long-term success comes from consistently scheduling time during the week to work on outreach. This is especially important when selling to the C-suite or high-level executives since reaching out once or twice likely isn’t going to cut it. 

 

What’s an underrated technique or strategy that youve found to be really effective in sales prospecting? 

Too often, sales reps immediately go into “pitch mode” when prospecting, but we’ve found significantly more success in providing relevant value-add content that applies to the prospect’s role or business — even if that content isn’t directly tied to our product. With thoughtful outreach, you can position yourself as a valuable resource to help the prospect with business issues they are facing versus just another sales rep bombarding their inbox. Once you have built a relationship and trust, you’re more likely to have a successful meeting.

One of our core values here is to “listen and learn,” and this is something that has been immensely helpful for prospecting. We use Groove.io to create templates and sequences to help us connect and form a relationship with prospects across multiple channels, and we always make a point to share with each other which approaches are resonating well with our prospects. We also use Gong, which records calls and serves as a great ongoing training ground.

Once you have built a relationship and trust, you’re more likely to have a successful meeting.” 

 

What’s an overrated technique or strategy that youve found to actually be ineffective?

I’ve seen many organizations take a very metrics-focused approach, asking reps to make X number of calls per week, send X number of emails, etc. This can often result in a one-size-fits-all approach, where reps are sending out very similar templates or leaving the exact same voicemails in order to hit these weekly numbers. Templates are a great starting point, but it’s extremely important to personalize and tailor your messaging to really resonate with each individual prospect.

Instead, we work with each person on the team to set their quarterly revenue goal and work backward to estimate how many new opportunities they need to create in the quarter to hit that goal. Then it’s about giving them the autonomy to manage their own schedules and do what they need to do to reach those goals. This promotes trust within the team and fosters an environment where reps are thoughtful about their outreach because they are focused on the end result like setting meetings and building their pipeline, versus more granular metrics.  

 

Justin Gurss
Account Executive

Gurss said voicemails need to be extremely personalized in order to work when outbound prospecting. Instead of leaving dozens of voicemails, the account executive said time is better spent reaching out to more contacts or researching target accounts. At AB Tasty, his team uses Outreach to accelerate their outbound prospecting activities.

 

When it comes to prospecting, what actions have you found to be critical to success?

You need to carve out designated extended hours (or even an entire day) to be successful at prospecting. You really can’t do it in short bursts. Why? Because you need to fail early and fail fast so you can mentally train yourself not only to make a great pitch, but also to prepare yourself for rejection. 

If I take an entire day to prospect, by the end of the day, I will have spoken to so many people that I’d be ready for anything since I’ve heard every possible objection and have had plenty of practice on how to respond. However, if I only prospect for 30 minutes and speak to one person, I’m more likely to fail because I haven’t had any time to practice and mentally prepare myself to make the best pitch. 

The idea is that you’re going to fail, and that’s okay. When you fail, you’re going to learn from your mistakes and get better with each call. 

The idea is that you’re going to fail, and that's okay.”

 

What’s an underrated technique or strategy that youve found to be really effective in sales prospecting? 

I always recommend prospecting based on job postings. Go to your job board of choice, and then search for keywords related to the solution you sell. Your search will then populate a list of companies that are looking to hire people with skills related to your services, which tells you they would potentially value your solution. You can then do two things: One is to prospect the manager of the potential new hire with messaging related to the job posting and the challenges that individual will be hired to solve. The second option is you can wait a few months and prospect the new hire with some insider knowledge about their role.

We’ve invested in Outreach, which has really helped accelerate our outbound prospecting activities. I used to be a big fan of using a date field in Salesforce combined with notes for my next outbound attempt, but with Outreach, I can add hundreds of contacts and easily create a cadence of scheduled follow-ups depending on the situation. 

 

What’s an overrated technique or strategy that youve found to actually be ineffective?

I’ve always found leaving voicemails to be highly ineffective for generating opportunities via outbound prospecting. Yes, there is a way to potentially spur interest from a voicemail, but the message that you leave needs to be extremely personalized so that salespeople and SDRs often spend far too much time on each one. Rather than leaving 10 voicemails that take 15 minutes each to prepare for, your time would probably be more wisely spent reaching out to more people or doing research on target accounts. Furthermore, I hate to say it, but the instant you leave a voicemail, most people will start to screen your calls, and will never pick up for you after that.

 

Matt Deis
Director, Sales 

Deis said he’s never agreed to a cold meeting over LinkedIn. Researching the right contact to speak with and creating a tailored, humanized email is more likely to get a response. Well-informed cold calls and relevant social strategy are the recipe for prospecting at IT company Electric.

 

When it comes to prospecting, what actions have you found to be critical to success? 

Identifying the “right person” to talk to. Especially when it comes to IT support for small-to-midsize businesses, you never know who the actual stakeholders are before you reach out. You have to be willing to engage with anyone who will talk to you and be fortunate enough for them to point you in the right direction to find the best person to speak with. 

Our SDR team actually developed a specific “right person” sequence in Outreach that we use once we have identified the IT stakeholder in an organization. That sequence has resulted in a 100 percent increase in meeting conversion rates compared to our standard Outreach sequences month over month. 

With everything going on in the world, it’s critical to lead with empathy first. Humanize yourself, then provide specific examples of ways in which you are either helping organizations like the one you’re reaching out to, or specific examples of how you can help the organization you’re reaching out to directly. This is probably the worst time to be sending pre-templated, blanket emails. People need relevant, actionable insights, if you don’t have them, you’re not going to get the engagement you’re looking for.

 

What’s an underrated technique or strategy that you've found to be really effective in sales prospecting? 

Putting a face to the name. I’ve never agreed to a cold meeting over LinkedIn. Ever. But when I receive at least a somewhat tailored email from someone who I have already connected with on LinkedIn (even without a message), I can’t help but connect the dots and see their face. It humanizes the person reaching out and makes it at least 20 percent more difficult to say “no.” 

 I’ve never agreed to a cold meeting over LinkedIn.” 

 

What’​​​​​​​s an overrated technique or strategy that youve found to actually be ineffective?

The idea of “social selling” needs to be re-framed. As I mentioned above, “social selling” should not be used as a singular, direct sales strategy. It’s a piece of your larger strategy for attracting attention and earning a prospect’s time. Especially in the earlier stages of your business, if you are posting on LinkedIn and social media waiting for the cows to come home, you’re going to go hungry. Combine the awareness of an appropriate and relevant social strategy with the urgency of a well-informed cold call to spur your prospect to take action.

 

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