Enterprise Sales Prospecting Strategies: 10 Steps For High-Performing Sales Teams

by Mohammed Shehu

Enterprise selling is a tough gig. It’s always a challenge to get in front of leads, qualify them for product-fit, and present your value enough for them to want to buy.

Enterprise selling takes different tactics and thought processes, but the end result is a customized solution for your client that helps them work faster, more efficiently, and more cost-effectively. It also doesn’t hurt that enterprise sales are some of the most lucrative transactions on the market, with SaaS sales alone totaling more than 322 billion in 2018.

In this post, we’ll look at why enterprise selling is so challenging and how to craft an enterprise sales prospecting strategy. But first:

What makes enterprise selling so different?

Enterprise selling is the art of going after big, complex deals with Fortune 500 companies, government agencies, or any business with over 50 employees.

But enterprise selling isn’t easy. Unlike SMBs, enterprises are typically guarded by layers of gatekeepers who will scrutinize your offer over a long period before buying. And for most sales teams, building an enterprise sales pipeline is no longer optional - it’s imperative to their sales strategy if they want to keep pace with their competitors and grow their bottom line.

Here are a few reasons why enterprise selling is so challenging:

#1 You are competing with other vendors

You’re never the only fisherman who has spotted the whale. In an age where new competitors are popping up every year, you’re likely competing with other vendors who are going after the same pool of lucrative B2B buyers - and your competitors may be selling their solutions to your target better than you are.

Enterprise buyers want more than just “features,” and they will test your ability to demonstrate value throughout the sales cycle. Your solution isn’t always a perfect fit for every business need. And unlike with SMB leads, an enterprise sale is more likely than not to fall through.

#2 There are more decision-makers

Selling to SMBs is relatively easier because you only have to go through one buyer (or two) to get the sale. The buyers (or champions) are directly involved in running the business, are keenly aware of their needs, and can sign deals quickly.

By contrast, enterprises have different managers and “owners” responsible for different functions at any given time. For example, if you’re trying to sell meeting lifecycle software to an enterprise company, you’d need to go through their Sales Manager, Finance team, Procurement team, and maybe even Legal before the contract gets signed.

#3 You need more data, analysis, and insights

Enterprise selling requires you to have rock-solid processes, accurate data to work with, and the ability to glean insights from that data to know which sales prospect to target, how to approach them, and what to offer that may match their needs at that point.

#4 Timing is critical

An enterprise sales team needs to be available when the target is ready for a new solution. Beyond investing in outbound sales to test the waters for intent and readiness, the team needs to nurture and stay in contact with leads in case a deal falls through or isn’t a good fit at that time.

All of these reasons make enterprise sales complex and challenging - but not impossible. In fact, by taking advantage of modern selling tools and strategies, your company can offer its customers better solutions and increase its revenue.

There are several strategies that can help sales leaders grow their enterprise pipeline. It boils down to planning for the long term and building a robust enterprise prospecting strategy to bring them closer to their revenue goals.

Plan for the long-term

As a sales leader, it’s easy to get caught up in the day-to-day tasks of enterprise selling, but long-term results require long-term thinking. Instead of solely chasing enterprise clients, spend some time thinking about the sales pipeline and prospecting processes you’re building for your company. How will they help in the next quarter? Next year? Next five years?

You can break this down into three sections:

  • Pipeline clients
  • Prospecting
  • People

Pipeline clients

Consider the type of pipeline clients you’re currently aiming at right now vs. the ones you’d like to be closing in the next 5 years. What differences do they have regarding revenue, headcount, industry sector, and jobs to be done? If you’re currently targeting companies with a turnover of $1mm a year, how would you need to improve your offer to successfully target companies hitting $10mm ARR?


How you prospect for clients plays a big role in the size and volume of deals you end up closing. Different enterprise clients engage with vendors in different ways, and it’s up to you to use the right tools on the right channels to meet them where they are.

For example, some enterprise clients might be more reachable through traditional advertising, but you might sway others more through trade shows. Others may be more amenable to annual reports and case studies that prove the efficacy of your product. Having a well-designed marketing and sales enablement strategy helps you reach key decision-makers at the right place and time in the buying process.


Lastly, it’s essential to train your team members on better ways to prospect, nurture, and close deals effectively. Beyond giving the right coaching and training to master outreach and engagement, every sales manager should invest in the right tools to facilitate prospecting and nurturing. These include tools like LinkedIn Sales Navigator or a CRM like Salesforce (learn more about what to look for in a CRM here).

You can also invest in sales coordination software like Momentum, which helps you sync critical sales data between Salesforce and Slack. Here’s what that looks like in action:

Build a robust prospecting strategy

A good prospecting strategy consists of two things: targeting the right channels and tracking your leads. Here’s a bit more detail on each.

Target the right channels

Prospecting is primarily about finding your ideal clients at the right place and time. There are several ways to accomplish this, which we’ll look at below.

Inbound leads

Inbound marketing involves creating the right content and conditions for prospects to find you instead of you seeking them out. SEO and content marketing are two key elements of inbound marketing, working together to increase your visibility and the relevance of your offer in the eyes of a potential customer.

SEO, or search engine optimization, involves improving your site and content to rank higher in search engine result pages (SERPs). There is technical SEO, which involves things like optimizing your site’s metadata, page structure, and image sizes (the larger your images, the longer it takes for your webpages to load, which hurts your rankings).

Then there is on-page SEO, which is more related to content and involves things like including the right number of keywords (keyword density), using the right header tags, and linking to other internal pages on your website.

Content marketing involves using content to answer customer questions, educate them about your product, drive interest and action, and position your brand as a thought leader in your space. Content marketing spans several channels such as social, email newsletters, and blogs and can deliver substantial value at a fraction of the price.

Getting started with content marketing requires putting together the right goals, tools, and topics.

First, you need to set the goals you’re trying to achieve with content. From a marketing perspective, the goals might be things like “brand visibility,” “improved search engine rankings,” and “lead generation.” From a sales perspective, it’s the latter that interests you - especially qualified lead generation.

Then, you need to use the right tools to get the job done. This includes SEO audit tools like Ahrefs and SEMrush and content planning software like MarketMuse and Frase. While it’s possible to churn out good content on a regular enough basis without these tools, it greatly boosts your efficiency and output when you do.

Warm emailing

By now, you’ve likely already emailed hundreds of clients, colleagues, and acquaintances within your target market. Which of these contacts could you reach out to and pitch your products to?

Previous clients might have further need of your services, while old colleagues at new workplaces might have the ear of a higher-up and be able to make a warm intro. Similarly, a contact who just returned from a 3-day conference might have met a potential customer that could use your services.

Keep those contacts warm and you just might uncover new opportunities to sell your product.

Cold emailing

Sometimes you won’t have a warm intro to the target company and will need to reach out and pitch your products directly. This is where cold sales emails come in. The art of crafting compelling cold sales emails has generated a lot of guides and books over the years, but the advice can be boiled down to the following key tenets:

  1. Personalize each email - use their name and title where possible.
  2. Make your pitch relevant to their role or needs - sell benefits, not features.
  3. Keep your pitch short and sweet - don’t ramble.
  4. Follow up a few times for maximum effectiveness.

Social selling

Social selling involves using social media channels to reach qualified prospects and pitch your products. Social selling leaders manage to create 45% more sales opportunities than their peers. and 75% of B2B buyers and 84% of C-level or vice-president level executives use social media to make purchasing decisions. This makes it a crucial channel for both prospecting and, most importantly, building product awareness.

Some great social selling tools include Outreach and LinkedIn Sales Navigator, which allows you to search for prospects by title, company, and name.

enterprise sales prospecting

Sales Navigator. (Source)

Trade shows

B2B buyers may respond well when engaged at a trade show booth and given a chance to interact with your products in person. It might be easier to get an appointment when you present in-person than via phone, live chat, or email. There are a few tips to keep in mind when using trade shows as a prospecting tool:

  1. Each trade show typically has a list of attending companies posted online. Identify your must-see companies and familiarize yourself with their business model, potential pain points, and relevant personnel.
  2. Reach out to the key gatekeepers on LinkedIn and introduce yourself ahead of the event. Invite each decision-maker to visit your stall later.
  3. Ask the right questions at the booth to ensure you qualify them properly for your service. This lets you know whether they’re looking to buy right now or still considering a purchase.
  4. Follow up diligently. Put those collected business cards to good use and set up meetings.

Cold calling

Ah, the dreaded cold call. This is an activity any seasoned sales rep quickly masters in order to close high-ticket deals with total strangers. Cold-calling requires you to build a database of high-quality prospects within your target niche, and there are plenty of tools that can assist you in both building your list and tracking your prospecting activities. These include Aircall and Toky.


When people talk about networking, you might picture a bunch of strangers in suits at a fancy lounge somewhere having drinks and snacks and exchanging business cards. The truth is that every interaction, engagement, or event during your day is an opportunity to network with a potential client.

Get into the habit of chatting with people at the airport, the coffee shop, and the local tennis court. Your conversation can lead you to somebody who knows somebody who knows a company that needs your services.


The best way to prospect for new business is through previous clients. This is not only because it’s 5 times cheaper to sell to a previous client than a new one, but also because previous and current clients might know other clients who need your solution as well. By simply checking in on past clients via email, phone, or social media, you might discover new opportunities to sell your solutions to a waiting buyer.

Track your leads

It’s one thing to kick your prospecting into high gear, but it’s quite another to track all this activity to make sure you’re maximizing your sales outreach. One way to do that is through a CRM (like Salesforce) which allows you to collect, manage, and follow up with new leads across different sales campaigns and channels.

Picking a CRM isn’t the easiest of tasks, so check out our guide to picking the right CRM for your business.

3. Ask the right questions

Finding the right leads is one thing, but what happens when you finally get them on the phone or meet in person? Successful prospecting hinges on qualifying leads to determine if they’d be a good fit for your product or service; otherwise, you’ll end up with hundreds of worthless leads that have low to no intent to buy.

There are plenty of questions you can ask, but most qualification questions fall under the following categories:

  1. Pain: What challenges are they facing, and how have they tried solving them so far?
  2. Time: When do they need this problem solved? Is there a deadline?
  3. Goals: How would solving this problem contribute to their goals? What does success look like for them?
  4. Budget: Do they have a set budget to solve this problem?
  5. Approval: Who needs to sign off on this, and what data or sales enablement content do they need to help them make this decision?

These 5 categories will give you plenty of insights into what they need, when they need it, and what they’re prepared to pay for it. You can then use this information to align your offer to their needs.

Start prospecting better

Prospecting for enterprise sales requires a different set of skills and processes to small business prospecting. There are more considerations like timing, approval processes, and internal stakeholders, and your offer needs to be more tightly aligned to their needs in order to stand a chance of closing the sale.

The first thing a sales leader should do is to plan for the long term in terms of their processes, prospects, and people. Beyond that, it’s essential to craft a robust enterprise sales prospecting strategy that leverages different channels and formats. Finally, asking the right questions ensures that you’re focusing your sales effort where it counts.

Looking for a sales tool to improve your deal room activity? Learn more about how Momentum helps high-performing sales teams to land more deals.

Move faster with Momentum