Your Guide to Powerful Sales Prospecting

Introduction

Take an honest look at your pipeline. Does it conjure images of Victoria Falls, or do pictures of clogged gutters come to mind?

If you’re seeing leaf-filled gutters, you’re not alone. Keeping the sales pipeline full is a constant challenge — with 69% of business-to-business (B2B) salespeople reporting that they do not have enough leads to make quota. Today’s complex buying cycles only complicate the problem. After all, the average buying committee is made up of six to 10 decision-makers and the overwhelming majority (77%) say their last B2B buying journey was extremely complex or difficult. With this in mind, what’s to be done?

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The simple fact is that no one likes to prospect, and chances are you’ve got an inconsistent approach — or you’re just plain winging it — and the results fail to fill the revenue pipeline. Not to worry: In this guide, you’ll discover powerful sales prospecting techniques that drive results.

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Four Fundamentals for Successful Sales Prospecting

What is Sales Prospecting?

Sales prospecting is the process of finding potential customers who are a good fit for your product/solution. This means identifying and initiating conversations with high-potential opportunities and proactively moving these individuals down the funnel until they ultimately convert into customers.

Overall, the formula for prospecting success is simple: More activity equals more quality connections that generate more wins. In practice, things are more complex.

Can You Prospect within Existing Accounts?

Closing the deal doesn’t stop competitors from trying to capture the attention of your new customer. You’ll need to consistently provide value, build solid relationships, and offer exceptional customer service to keep the business. Luckily, these activities will also set you up to sell additional services. Here are the tools you’ll use for prospecting existing customers:

Active listening: A recent study by LinkedIn found that active listening is the number-one quality that buyers look for in salespeople. While buyers may prize this crucial skill, sales managers often fail to prioritize it. However, it’s the first step to demonstrating the empathy that will build mutually-beneficial customer relationships.

O-P-C Questions: An effective questioning process that uses opening, probing, and confirming questions will help you diagnose additional problems within the organization and identify areas where your company could provide additional value.

Stellar Customer Service: It costs five times as much to attract a new customer than it does to retain an existing one. Adopting the role of a trusted business consultant will position you to provide an outstanding customer experience. Continuous engagement is paramount here. Not only will that allow you to build the relationship, but it will also help you identify potential issues early-on.

Who is Responsible?

The short answer is that it depends on your company’s structure, size, and industry — with different companies employing a various mix of inbound and outbound sales prospecting techniques to drive results.

Marketing: Your marketing colleagues are tasked with generating leads, but may not actively prospect. Their leads are the results of specific advertising campaigns or website interactions like ebook downloads, podcast subscriptions, and “contact us” forms.

There’s no exact science for determining how many of these marketing leads will become sales qualified leads. However, if sales and marketing work together to create customer profiles built around the pain points that your solution is uniquely well-suited to address, then you’ll be able to more effectively target high-potential opportunities and increase the overall quality of leads.

Sales development reps (SDRs): Larger companies tend to have dedicated specialists who work the phones, send value-added emails, and share relevant insights on social media day-in and day-out to deliver prospects to account executives (AEs), whose job it is to move the sale forward. SDRs often work from large lists of leads in the hopes of establishing contact and identifying qualified opportunities.

Sales reps: Salespeople have many time-consuming tasks to check off their daily to-do lists. Once you add up the time spent on non-selling activities like administrative tasks, updating the CRM, expense reports, and internal meetings, the average rep spends just 37.67% of their time selling. It’s understandably tempting to rely on others to fill the revenue funnel, but driving measurable results always requires strong and proactive prospecting on the part of salespeople — which means dedicating more than 10 hours per week to prospecting within a consistent framework.

Leads vs. Prospects

What is a prospect in sales? How do leads become prospects? Here’s how to tell the difference — and why it matters.

Leads are individuals who have self-selected to some degree and expressed interest in your company — maybe they’ve traded their email address for your latest ebook, spent some time clicking around your website, or engaged with a lead gen campaign. Regardless of their pathway, leads are potential buyers who are familiar with your brand but have not been qualified as likely buyers.

Prospects are potential buyers who have been vetted and deemed qualified. These individuals most likely align with the personas your company typically sells to and have high potential to become customers. You’re looking for circumstances where your company can provide measurable value to both the individual buyer and the organization — which means you’ll need to target prospects who have the authority to buy and come to an agreement that your solution delivers enough value to prompt change.

Ultimately, it’s the problems worth solving that are the most pressing and have the urgency to bring about change — which is why you’ll need to start by developing the business acumen to identify them in the first place.

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Key 1: Building Business Acumen:
Talking the Talk

It’s no longer enough to have the best product/solution out there. You must also be equipped to win the fight for capital at the CFO level, which means developing the acumen to engage executives. And with 88% of buyers describing the salespeople they do business with as “trusted advisors,” it’s a skill you’ll want in your toolbox.

pillar-sales-prospect04The traditional approach to sales prospecting involves identifying a pain point and selling your solution to fix that problem. Sounds simple enough, right?

Let’s look at a common scenario: Say you sell a network security solution and you target a company that just underwent a rapid digital transformation — only, after several attempts to connect… crickets. At this point it’s only natural to ask, “Why are executives not returning my calls?” But that’s not the path to effective prospecting — instead, you should ask, “What have I done to incentivize executives to pick up the phone?”

After all, executives spend their time before their money. A successful sales prospector realizes the difference between urgent business issues and pain points: Just because an organization has a problem that your product/solution solves, it doesn’t necessarily mean it’s a problem worth solving. Telling the two apart requires business acumen.

To be seen as a value-added interruption, you must come prepared to link your solution to urgent business concerns and tie it to some sort of financial metric. You don’t need to start googling MBA programs, but this journey will take some commitment and a curiosity about your prospect and their business.

Start by asking yourself these seven questions to fully imagine the persona you’re targeting and develop messages that resonate:

● What is going on in this industry?
● What types of companies am I selling to?
● How do they make money?
● Who are their customers?
● What stage is the company in?
● Are they profitable?
● Who runs the show?

How do you find this information?

If the company is public, you can get straight to the heart of things by looking at their balance sheets, income statements, and cash flows. It’s also important to broaden your scope and see how the prospective company stacks up against their competition. All too often, organizations look good in a vacuum but pale in comparison to their industry peers. Staying current on industry publications and setting up Google alerts for competitors are excellent tactics for identifying trends and synthesizing key information. Social networks are another resource to leverage. Understanding the content that a sales prospect is liking, sharing, and commenting on will help you craft messages and questions that pique interest.

Overall, business acumen is about developing financial literacy and applying that to ongoing research. If you’re able to stay current on emerging trends, you’ll set yourself up to more easily identify patterns and discuss issues that are likely already on the prospect’s radar.

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Key 2: Qualification: Maximizing Prospecting Time

Nothing wastes time and resources faster than chasing opportunities that will never close. Often salespeople will sink hours — or even weeks and months — into establishing contact, moving the relationship forward, and delivering demos only to encounter radio silence at the end of all that effort.

The trick to ending this cycle and maximizing your prospecting time is developing the strategic prospecting skills that separate the shoppers from the buyers. To identify and close high-potential prospects, start by evaluating each opportunity in terms of these critical questions:

Should they buy from you?
Take a hard look at the individual and attempt to match them against your customer profiles and personas.

Consider where your organization has had success in the past, e.g., same industry/role/challenges, different industry/role/similar business issues.

Is it worth it?
Remember: Not every problem is worth solving. All too often, sales reps fail to uncover and articulate value that is meaningful to potential buyers.

The modern B2B sales cycle has bifurcated — having the best solution is only step one. Be ready to demonstrate the short- and long-term value using some sort of financial metric that will get an executive’s attention. Will there be a bump in revenue? Are they going to see incremental productivity increases? Will it drive cost savings?

Recognize the barriers to change: People and organizations are resistant to change for a multitude of reasons. Be prepared to communicate across the company you’re selling into to increase buy-in.

Can they buy?
Ensure that you’re talking to an individual who has not only the need, but also the authority to buy.

When will they buy?
People buy from people: It’s your job to uncover and understand a potential buyer’s motivations by forging meaningful connections. If you’re able to connect those motivations with your solution, you’ll create a dimension of critical urgency.

Uncover their buying process and align with it: Modern B2B sales is more about facilitating buying than it is pitching and selling to sales prospects.

Build a plan to realize value: Work with a prospect to understand exactly what will be required to bring about the impactful changes that your solution can deliver.

Ultimately, organizations restructure, industries change, and political environments shift — causing opportunities to come in and out of qualification frequently. To invest your time in truly high-potential sales prospects, realize the need to continuously requalify opportunities. By adopting a mindset that treats qualification as an ongoing process instead of a discrete event, you’ll develop effective prospecting techniques that drive results.
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Key 3: Creating a Sales Prospecting Cadence: Developing Discipline & Consistency

Determining the Right Volume for Effective Prospecting

Before you can create a prospecting cadence that drives revenue, you’ll need to know how much activity is actually needed.

Start by looking at your goals. Once you’ve determined the number of transactions needed to hit your targets, simply work backwards to find the volume of sales prospects needed to generate those results.

When formulating a plan, pay particular attention to your average win ratio to ensure that the data you used to calculate this is accurate — and always err on the side of caution. If your average win ratio falls between 1 in 3 and 1 in 4, plan on closing 1 out of every 4 opportunities — your pipeline will thank you later.

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Building a Strategically Choreographed Prospecting Strategy

Once you’ve calculated the total prospecting volume needed to crush quota, look to your process. Remember that B2B buyers are inundated with messages, making it difficult to capture their attention without a prospecting strategy. Building a sales cadence will help you develop consistency and leverage the way our brains are wired to generate higher response rates.

Start by carving out non-negotiable blocks of time on your calendar and sticking to them. If you’re planning to hit the phones hard between 10am and 12pm on Monday mornings, commit to doing it. If you don’t respect this time, why should others? Don’t skip on time allotment either. Only 18% of sales reps spend nine hours or more on weekly prospecting — aim for two hours daily or 10 per week to develop a pipeline that results in quota attainment.

Of course, life will get in the way. Fire drills, customer needs, and last-minute requests from management are inevitable, but never cancel your sales prospecting time — move that block of time to later in the day.

The next step is research. Before you can connect, you’ll need to understand the individual you’re targeting. This doesn't have to take hours. Plan on spending 15 to 20 minutes researching the prospect’s industry — and dedicating 10 minutes to learning more about the company itself and another 10 for the individual.

From there, you’ll need to outline your cadences. The ideal sales prospecting cadence will vary based on a potential customer’s industry and role. If you’re targeting the CMO of a tech company, you’ll want to start with LinkedIn — given their inclination for staying connected. On the other hand, if you’re going after manufacturing executives then picking up the phone might be your go-to start.

Remember to always provide value from the very beginning. If you’re trying to connect with that CMO and you start with LinkedIn, aim to thoughtfully engage. This might take the form of reading the content that they’re sharing and leaving a well-researched comment and sharing an intriguing resource in return. Two days later, you might follow up with an InMail message and another resource. Your next move might be an email that shares how you’ve provided impactful value to similar companies in the past and asks to set up a short call.

The key is to stay consistent. By never going more than five business days between touches, you’ll stay top-of-mind and significantly increase your odds of connection — but you have to be prepared to put in the work. A typical sales prospecting cadence may involve 15 to 17 touches across 20 to 24 business days.

More than anything, don’t be afraid to pick up the phone! Half of B2B sales reps fear making phone calls. By developing the discipline and confidence to include calls in your cadence, you’ll set yourself apart and open doors that may otherwise remain firmly shut. And this isn’t just for warm opportunities either — yes, cold calling still works in this day and age.

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Key 4: The Tools of the Trade:
Leveraging Your Tech Stack

What is a tech stack?

A tech stack is the combination of software and web-based tools that are woven together to help salespeople improve productivity and effectiveness. These tools are designed to help you identify possible opportunities, manage follow-up and cadences when prospecting clients, and improve the quality of data throughout the sales process.
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As you plan to implement your prospecting strategy, seamlessly integrating your tech stack will allow you to create a sustainable prospecting process. If leveraged correctly, tech stacks can enable sellers to scale their efforts while maintaining that personalized approach that is so crucial to forging lasting business partnerships — but first you’ll need to fully understand when and how to implement each tool.

Sales Tech Categories

1. Identification & Research
These are the tools that will help you compile lists of individuals who align with the personas your company typically sells to and have high potential to become qualified prospects. They typically work off a set of criteria — industry, revenue, team size, etc. — to provide a longer list of possible opportunities. While these tools are tremendous time savers, they don’t necessarily provide detailed account information. It’s up to you to personally vet these contacts to ensure accuracy.

Popular examples include: Clearbit, Datanyze, DiscoverORG, and ZoomInfo.

 2. CRM/SFA: Data Organization & Tracking

Gone are the days where sales reps are tied to business cards, address books, and poorly-organized Excel spreadsheets. These tools act as the collective memory for sales teams, and are where you’ll store important account information and track every interaction to form comprehensive views of accounts. While we have seen advances in these tools, the complete process has yet to be automated — ultimately these tools are only as accurate as the data being imported. To get the most value out of your CRM/SFA, develop the habit of regularly updating the system.

Popular examples include: Copper, HubSpot Sales, Microsoft Dynamics, Nimble, Pipedrive, PipelineDeals, Salesforce, and SugarCRM.

3. Outreach Automation, Tracking, & Analysis

This is the segment of sales tech space that traditionally sees the most innovation. From AI-backed tools that track and analyze sales calls to email sequencers to automatic dialers, this tech aims to automate tasks, scale efforts, and provide insight into what tactics convert sales prospects into customers. They can also help you dial in workflows by designing evolving task lists that support your prospecting cadences.

Popular examples include: Chorus.ai, Engageio, Gong.io, Outreach.io, and Reply.io.

If you are not leveraging technology in your sales prospecting process, you will lose your relevance in a tech-enabled world. At the same time, all that tech makes it awfully easy to hide behind a screen. The key is to find balance: Leverage your tech stack to automate, amplify, and accelerate your efforts — but never forget that sales enablement tools must be layered on a solid foundation of human connection.

What about Social Selling?

1) Building a LinkedIn Presence

B2B buyers are sophisticated shoppers. They regularly use social platforms to research options, companies, and the salespeople they’re interacting with. When you put the work into developing your LinkedIn presence, you amplify your personal brand, increase credibility by elevating your status as a thought leader, and build extensive networks of quality connections who can help you better connect with the sales prospects you’re targeting.

Be sure to put your best foot forward. It’s not uncommon for your LinkedIn profile to be the very first thing potential clients see when searching for you online. Start by making sure your information is up-to-date. Next, look to your bio. A strategically crafted bio not only helps viewers immediately grasp your expertise, but it can also help you show up in searches when prospects begin researching particular solutions. The same goes for your experience section. Strive to stay current and offer succinct and meaningful narratives of your current and previous roles. You’ll also want to highlight accomplishments as much as experience, but this is more than just a resume — it’s the definitive narrative of your personal brand.

Don’t forget groups. Joining relevant industry groups is a fantastic way to increase your status as a thought leader and forge connections with peers who might be in a position to refer you to potential buyers in the near future.

2) LinkedIn Sales Navigator

Sales Navigator has become pervasive for most B2B sales teams — and with good reason. This powerful system helps sellers identify new prospects, track account interactions, and stay on top of critical changes at target organizations — like funding announcements and senior leadership changes.

But just like any other sales tech tool, a lot depends on how you set it up and implement the insights you receive. The key here is to be mindful when you’re creating preferences — particularly at the role targeting level — and updating those preferences to match industry/market changes and any shifts in your prospecting strategy.  

3) Social Selling

We’ve all accepted an invitation to connect on LinkedIn, only to be immediately hit with the hard sell. This is the last thing you want to do. Instead, your sights should be firmly fixed on relationship-building.

Once your profile has been optimized to support strategic prospecting, it’s time to start gathering social insights, building relationships, and increasing thought leadership status. Begin by observing what content your prospects are putting out there and attempt to engage with it in meaningful ways. You’ll also want to share your own, but don’t get bogged down in self-promotion. Consistently sharing content that provides immediate value is the quickest path to building your brand. It’s also an excellent way to grow your network because it incentivizes others to connect.

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Key 5: Executive Access:
The Benefits of Selling Higher

Why sell to executives? The answer is simple: You can’t sell to someone who doesn’t have the authority to buy. Gaining access to an executive early in their search for a solution can also help you cut down on competition and present the opportunity for a bigger deal by developing a more comprehensive and integrated solution to their business concerns.

Remember: Almost one-third of all sales opportunities stall out because salespeople attempt to sell to someone who doesn’t actually have the power to sign. To sidestep this pitfall, you’ll need to go to the top — but you won’t get very far if you don’t know how to win over the gatekeepers who guard executive access. pillar-sales-prospect05-1

Administrative Assistants

It’s often the role of these gatekeepers to place a moat between you and the executive you’re trying to sell to. While it may be tempting to view them merely as obstacles to overcome, they can be your best friend: These individuals often have tremendous insight into the executive you’re targeting, their schedule, and the most pressing concerns facing the business.

Always approach these individuals with respect and transparency — and don’t be afraid to ask for help. By clearly communicating your intentions and asking their advice on how to best reach the executive in questions, you’ll encounter bridges instead of gates.

Middle Managers

When attempting to partner with middle managers, begin by diagnosing their motivations. Are they trying to hold on to power? After all, spearheading projects and being the only point of contact for vendors conveys a certain amount of authority. Or maybe they’re playing in their own sandbox and resist you branching out into the organization where this project may not be a priority. Regardless of what those motivations are, you’ll never know unless you’re able to partner with them — which often requires striking a bargain.

Providing valuable resources like demos in exchange for executive access is a proven strategy. However, you’ll want to make sure that you’re on the same wavelength: Set expectations early in this relationship to ensure you’re not wasting your time.

Technology

While it’s important to carefully consider the persona of the executive you’re targeting when developing your prospecting cadence, there remains an element of the unknown. Sure, CMOs are likely active on LinkedIn — but are you sure they’re posting content and responding to InMail personally? Manufacturing executives may be used to being inundated with emails, but when’s the last time they received something of immediate value in the mail?

All the research in the world won’t tell you an individual’s preferred communication method or style, which is why you should plan to incorporate all forms — especially phone calls.

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Key 6: Delivering Value: Understanding Every Sales Prospect’s Motivations

We know that top sellers win by demonstrating value. In fact, sales professionals who exceed quota by 25% or more are significantly more likely to list price as a top factor in securing deals — but even more likely to list ROI. As you begin building your cadences and prospecting clients, be sure to provide value from the very beginning.

Credibility Introductions

The best sales reps are often the most gifted storytellers. They draw on previous results to capture a buyer’s attention, engage authentically, and establish credibility early in the sales process — and there’s no better way to do this than with a value-based story.

Value-based stories are the linchpins of effective credibility introductions. These personalized messages resonate because prospects see themselves in the story and realize that you could bring them similar value. But you only have one shot to get it right, which is why research and practice are so important.

Research: Here’s where developing the business acumen to engage executives really starts to pay dividends. Dive into those financial reports and industry journals to identify critical business concerns that the prospect is likely facing. The more clearly you can articulate the problem, the more likely a sales prospect is to believe that you can identify an impactful solution. It also helps to pay attention to the terminology and use language that best fits the potential buyer’s role and industry. That way the impact of your message doesn't get bogged down by confusion and the need for clarification.

Next, look to your own successes. How have you driven results for similar roles in similar industries? Even if you’re new to selling, past case studies provide excellent material and the vital specifics to demonstrate that your solution can resolve a problem that’s worth solving.

Practice: It’s intimidating to deliver a use case for why a prospect should trust you and your company to deliver meaningful value in less than 30 seconds. That’s why it’s crucial to practice, practice, practice. If you can deliver your credibility introduction with ease while exercising or wrangling children, you’ll find yourself on solid footing at the start of every sales call. Don’t forget to time yourself either. While there’s no hard-and-fast rule that says you have to stick to under 30 seconds, consider the prospect’s perspective. Better to stick to a prospect-centric approach and foster engagement rather than including every relevant point in your story.

Uncovering Value

Your ability to understand a prospect’s point of view, circumstances, and motivations will drastically impact your odds of closing the sale. In order to gain these insights, you need to get out of your own head and into the mind of your potential customers by adopting a prospect-centric approach.

The truth is value looks different depending on who you ask. A 20% increase in cost savings may be enough to convince one prospect, while another might not feel that the impact justifies the risk. Powerful value propositions are one thing, but if you’re able to guide the prospect to conclude the probable value on their own, you’ll help them to build a convincing business case. By taking on the perspective of the prospect and uncovering both their business and personal motivations, you’ll connect to urgent issues and motivate them to take action.

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Key 7: Measuring Sales Prospecting Effectiveness

You can’t improve what you don’t measure. Set off to establish a baseline for effective prospecting by diving into past results. By analyzing your prospecting results, you’ll be able to identify trends that will inform future strategy.

The Initial Meeting

There’s no better place to start than at the beginning. Consider your top three challenges when landing that crucial first meeting. Are you having trouble accessing decision-makers? If so, you’ll need to up your game when it comes to winning over gatekeepers. Prospects not returning your calls? It could be time to redesign your cadences and make sure you’re using an omni-channel approach. Maybe you’re not even sure who to approach. If so, it’s likely time to dedicate more effort to research, particularly on LinkedIn.

Prospecting Methods

With the jump to virtual selling, you’ve probably tried your hand at a webinar or two, but are they resulting in leads? What about social selling or break out rooms in virtual meetups? The key here is to be methodical. Your data is only as useful as it is accurate, which is why regularly updating your CRM is so crucial. Once you’ve identified patterns of success, take it one step further and see if there are correlations to particular business challenges or roles.

Start Prospecting

Prospecting doesn’t have to be a sporadic and nerve-wracking process. By adopting a value-based strategy and building your toolkit of strategic prospecting skills, you’ll fill the revenue pipeline while forging the authentic connections that lead to mutually beneficial partnerships. If you take nothing else away from this guide, remember this: More calls means more qualified opportunities and more wins.