Enterprise Sales Cycle Management: An Essential Guide

Apr 13, 2021
Mohammed Shehu

Sales are the lifeblood of any B2B company, but a long and complex sales cycle with a large enterprise company can be taxing on the time and resources of your sales team. As a sales leader, assessing your sales model to identify which aspects of the buying cycle to improve is key to moving each enterprise deal from quote to contract faster. This article outlines 5 key elements of the enterprise sales cycle that you can optimize:

#1 Prospecting

#2 Qualifying new leads

#3 Making an offer and handling objections

#4 Structuring the deal

#5 Customer success and support

Let’s dive in.

Section 1: Prospecting

Prospecting is the first element to get right in the enterprise sales process. It involves finding and engaging with potential customers who are a good fit for your product. Prospecting can be broken down into 4 key steps:

  1. Craft your ideal enterprise customer profile
  2. Research your market thoroughly
  3. Identify the right channels for prospecting
  4. Automate your customer outreach and engagement

1. Craft your ideal enterprise customer profile

Defining your ideal enterprise customer profile is crucial to understanding how they think and behave so you can craft an effective lead generation strategy. It involves finding out who they are, what their roles entail, and which of their pain points your product can address.

2. Research your market thoroughly

Whether at the SMB or enterprise level, it’s essential to understand the context of the market in which you operate. For example, you may have competitors who offer a similar product at a competitive price-point or one that needs much less onboarding than yours. The more competitive your space is, the harder enterprise selling becomes - especially if you have a complex sales process that involves multiple decision-makers. Find out how big the market is and what trends are emerging to get ahead of the game and create a competitive advantage.

3. Identify the right channels for prospecting

Now that you’ve defined your ideal customer profile and market context, it’s time to figure out what channels are right for reaching out to those prospects. You can start with known contacts at your target companies or any of the following places:

  • LinkedIn: Many enterprise prospects are on LinkedIn, but a haphazard prospecting strategy won’t serve you well. Instead, connect with relevant people who might be a good fit and start building relationships with them. Learn where and how they work and what their KPIs are so you can tailor your sales pitch accordingly.
  • Online communities: Look for online communities where people talk about problems you can solve with your product. These might include Quora, Reddit, Stack Overflow (for technical products), Facebook Groups, and even Twitter threads. Establish a presence on those platforms and answer any relevant questions that come up.
  • Conferences and trade shows: Trade shows allow you to build brand awareness and generate leads in-person. Before the event, network with contacts you can later meet with.

4. Automate your customer outreach and engagement

It can be time-consuming to contact and follow up with each enterprise client manually, so invest in automation tools to streamline the process for you. Many of these tools can automate the process of sourcing, connecting with, and advancing sales conversations with new prospects. Examples include Octopus and LinkedIn Sales Navigator for lead generation and outreach and ActiveCampaign for email engagement.

Challenges with enterprise buyer prospecting

Prospecting doesn’t come without its challenges. Even when managed correctly, it can still take time to find and acquire a new enterprise customer. If you’re struggling to find new leads, determine how you can add value to customers through an ongoing activity.

For example, you can create valuable content across your channels that helps your target audience do their jobs better. A second option is to connect your target audience with job opportunities that will need your product (e.g., helping salespeople find jobs that will need CRMs, which you happen to sell). You can also sponsor relevant events to create brand visibility (such as Grammarly, a writing tool, sponsoring book fairs or book clubs). Finally, explore paid advertising channels like Facebook, Google, or LinkedIn ads as lead acquisition channels.

For each lead generation activity you choose to execute, we recommend evaluating the following:

  1. The value proposition of your activity: When an enterprise prospect understands how they can benefit from your product, they’ll be more interested in what you have to say.
  2. The financial cost: If you’re going to spend $10,000 on a conference booth that only produces 10 leads, you may want to consider other ways of generating leads at a more favorable cost per lead.
  3. The time cost: Ensure the time cost will be reasonable with regard to expected results. This helps you avoid spending too much time on something that will return little value.
  4. The competition: If there’s a lot of competition in that space, consider whether it makes sense for you to launch a similar initiative or find another way to stand out from the crowd.

Use the following tips and tricks to maximize your enterprise prospecting activities:

  1. Know what you’re selling: Deeply understand what your product does and the value it will provide for customers before reaching out. Be clear about the pain points your product addresses and its benefits and features. This makes it easier to tailor your pitch to your audience.
  2. Build relationships: Reach out early and often to build relationships and get referrals. If you don’t immediately land the deal, there might be an opportunity to do so in the future (either there or at another large company).
  3. Work quickly: Once you’ve identified a potential customer, don’t delay reaching out to them with a timely and relevant pitch. If they don’t respond straight away, try again in a few days via phone or email.

Prospecting can fill your pipeline with many new leads, but not all leads are created equal. You still need to determine which leads are worth your time and effort, and that’s where lead qualification comes in.

Section 2: Qualifying new leads

Qualification involves figuring out if an enterprise prospect is a good fit for your product. It requires meeting (or e-meeting) the prospect, asking the right questions, and listening to their feedback. To avoid a long sales cycle, you’ll want to quickly find out about their business needs, challenges, budget, timelines, and authority to close a deal.

To make your qualification process as efficient as possible, you can use two lead qualification methods: BANT and MEDDIC.


BANT stands for “Budget, Authority, Need, [and] Timing.” This framework checks whether a prospect meets your qualification criteria by asking these four questions:

  1. Budget: Can they afford your solution?
  2. Authority: Are they authorized to buy? Can they make the decision alone, or do they need approval from other stakeholders?
  3. Need: Do they have a specific problem that your product can solve?
  4. Timing: Is it a good time for them to buy right now?


MEDDIC stands for “Metrics, Economic Buyer, Decision criteria, Decision process, Identify pain, [and] Champion.” It checks whether an enterprise prospect is a good fit for your product by asking these six questions:

  1. Metrics: What stats and facts do they care about? What data about the problem, your product, or the results are they interested in?
  2. Economic buyer: Is the enterprise prospect a sole decision-maker or are there multiple stakeholders involved? Who else within the company needs convincing?
  3. Decision criteria: What criteria do they use to make their decision? What features are a must-have for them in any new product, and how does your product stack up against that checklist?
  4. Decision process: How long does their internal buying process take, and what metrics do they use to score each proposal?
  5. Identify pain: What pain points do they have, and how will your product solve them? Which pains are a bigger priority for them right now? What tangible impact (in terms of time, money, or human resources) are these problems having on their business?
  6. Champion: Who within the company can advocate for your product on your behalf and influence the decision-making process?

While MEDDIC is a bit more comprehensive than BANT, both qualification methods work towards the same outcome: determining whether an enterprise client is a good fit for your product at any given time. After you’ve sourced a lead, qualified them, and determined they’re a good fit, it’s time to present your offer.

Section 3: Making an offer and handling objections

Your goal with an offer is to clearly articulate your product, what it does, how it can help your prospect, and why they should specifically buy from you and not a competitor. You can make an offer in-person, over the phone, or via email.

In-person meetings offer you the chance to present your offer through an engaging keynote presentation or live demonstration (depending on what you’re selling). Phone offers are not as impactful as in-person offers (as you can’t read facial expressions or body language), but they’re still intimate enough to close the deal. Email offers the most flexibility for both parties, as you can take your time to craft a compelling offer, and they can deliberate and respond appropriately.

Of course, not all offers are accepted immediately. Handling objections is a normal part of the sales cycle, so let’s look at that next.

How to handle sales objections

An objection to your offer isn’t necessarily the end of the road. Sales objections can come from the prospect themselves or their internal team and could stem from any of the following reasons:

  • They don’t understand your product well enough. In this case, give them relevant sales enablement content to help them make a decision.
  • They don’t see your product as a priority at the moment. If so, cultivate and maintain the relationship and reach out again when they need it more urgently.
  • They think your solution will cost too much. Ask them for details about other solutions they’re considering so you can show them why your product is better value for money. Failing that, consider restructuring your price to suit their budget better.
  • They aren’t convinced of your company’s credibility or track record in solving this particular problem. Show proof points, testimonials, or case studies of similar customers who have had previous success with your product.

As you respond to these objections meaningfully, the client will either return with more questions or move forward with the deal. Let’s look at how that can play out next.

Section 4: Structuring the deal

Once a prospect decides to buy your product, it’s time to close the deal. Closing the deal involves documenting the deal terms, receiving payment, and implementing the solution.

Contracts play a significant role in enterprise deals because they lay out expectations on both sides. A typical contract will outline the agreement’s scope, identify key milestones and timelines, establish a payment schedule, and outline any relevant terms and conditions.

Implementation is another crucial element of closing the deal. Depending on your product, your client might be able to implement your solution themselves without your help. For example, if you’re selling a cloud CRM solution, a client could easily create an account on your platform, configure it, get users on board, set up deals, etc., all on their own.

Other cases are more complex and require your support for successful implementation. If you’re selling a warehouse management solution to a multinational e-commerce company, for instance, you may need to coordinate the implementation with their teams across different geographies.

When structuring complex deals, you need the right tools to deliver information quickly so you can make decisions faster. For example, if you use Salesforce, you can set up your deal room in Slack to access deal data on the fly. Momentum syncs deal data between Salesforce and Slack so that your team is never out of the loop.

Sales coordination tools (like Momentum) are a must-have for enterprise sales teams who value speed and efficiency when structuring deals. Once your product is up and running, it’s time to understand how they are using the solution and if they’re getting value from it. This is where customer success and support come in.

Section 5: Customer success and support

The sale is not the end of the engagement. After your customer starts using your product, your job is to help them extract maximum value from customer success and customer support.

#1 Customer success

Customer success involves everything you do to make sure your customers are using your product correctly and getting value from it. This can include:

  • Showing them how to use your product
  • Providing training that covers new or existing features
  • Configuring third-party integrations with your product
  • Providing regular feedback on progress made, ROI achieved, etc.
  • Establishing a “help desk” where customers can log bugs or submit feature requests
  • Performing product upgrades as needed

#2 Customer support

There are many channels you can provide ongoing customer support through, including the following:

  1. Live chat: This is a direct, real-time communication channel with customers who have questions or suggestions. Live chat gives you real-time context and helps you provide quick assistance.
  2. Email: Email is a convenient way to provide support and document all customer communications.
  3. Phone calls: This channel works best for customers who need urgent support and want to speak to a customer rep.
  4. Self-service support: This is training material that your customer can access and view on their own, 24/7.
  5. Social media and community forums: You can monitor social media and online forums to respond to questions from your customers quickly.
  6. Chatbots: A chatbot allows you to give real-time support to customers without involving any humans.

Build an effective sales cycle

As a sales leader, finding ways to improve your customer’s buying process and shorten the enterprise sales cycle can help you land more deals. Using the above framework allows you to organize your time and efforts more effectively and optimize your sales funnel for success. While certain aspects may require sales training for your sales organization, the investment is well worth the outcome.