For B2B tech companies, there’s nothing better than closing a huge sale. You know, the ones where you crush your revenue goals in one fell swoop, making more than you would in a year or two working with smaller accounts. Mastering enterprise selling is a lofty (but not unattainable) goal.

Enterprise selling, particularly to Fortune 500 companies, isn’t without its challenges. The process often:

  • Is high risk and complex
  • Involves many stakeholders
  • Consists of a long sales cycle (6+ months)
  • Requires a lot of investment

In this article, we’ll share some tips to help you overcome some of those challenges and ramp up your enterprise selling strategies to land more Fortune 500 accounts.

Fortune 500 stat


1. Pinpoint the Purchasing Power

With most large Fortune 500s, there may be a number of people with a title who can seemingly help move your enterprise selling forward. Truth is, with any large enterprise-wide purchase there are going to be a few stakeholders involved. So it’s really just a matter of finding and getting in front of the right people. Here are a couple tips to help you do that:

Do your homework.

Before you reach out, do some research so your cold calls can start off a little warmer. By simply perusing the organization’s website or social media profiles on LinkedIn, you can glean a lot of valuable information to zero in on the right person. Start by figuring out the size of the company, which will inform you whom you want to reach out to.

It’s easier with small and medium-sized businesses (SMB) — usually CEOs, VPs, and even Sales Directors have purchasing power. While those contacts are still great to find at larger enterprises, they can be harder to track down. Start by researching specialized roles by region — West Coast Sales Manager, North American Business Development Manager, etc.

Fortune 500 titles and roles

Seek out common connections.

Once you’re confident you know the right title to target, dig a little deeper with your research. Find the LinkedIn profile of the person with the title that aligns with who you believe to be the decision-maker. See if you or any of your colleagues have common connections with the person or company in question. If you find a connection, ask for an introduction!

If you don’t, you’re still in good shape because you found the decision maker’s profile which can be a goldmine of helpful background information (how long they’ve been with the company, previous positions, skills & endorsements, education, awards, hobbies, etc., that help you personalize your pitch).



2. Be Persistent

You can estimate it, but you never truly know when someone might answer their phone or check their email. Timing and persistence are key to getting a response with enterprise selling.

Enterprise sales almost always involves multiple touchpoints with multiple people regardless of how many decision makers there may be. With much longer sales cycles, the process can go on for as long as two years in some cases!

Our sales development team, for example, has perfected an ideal cadence through a 24-touchpoint lead follow-up process that uses a blend of LinkedIn, phone, and email. And all of those touchpoints are simply an effort to get the first meeting!

It starts with three successive touchpoints:

  • A quick LinkedIn message to further educate and build trust and credibility early. This shouldn’t be a sales-heavy message, just a soft call to action.
  • Immediately follow-up with a phone call. LinkedIn can be a slow-developing channel depending on how often the prospect checks their account. It’s a good start, but getting them on the phone asap is the ultimate goal.
  • If there’s no answer on the call, leave a voicemail and follow-up with an email.

From here the process gets phone-heavy, averaging 3-4 calls per every email you send.

The entire 24-point process consists of about 5 emails and a LinkedIn message or two. The rest are phone calls.

Ultimately, it’s important to strike a balance between giving enterprise leads time to respond and being persistent so they don’t move on to another service provider. As long as you continue to be professional, build trust, and educate along the way, most prospects will respect and appreciate your staying top-of-mind with regular follow-ups.



3. Adjust Your Strategy Accordingly

Moving Fortune 500 prospects down your sales funnel is rarely a linear process. While persistence is important in working your nurture process, refining the process as you go is just as crucial.

Enterprise selling is all about testing, tweaking, and optimizing based on the combined knowledge of your internal and external teams.

You have to constantly adjust with enterprise selling programs, keeping your ear to the ground to understand what’s working and what isn’t.

Take Tata Communications, for example. A “digital ecosystem enabler” who targets high-tech Fortune 500 companies saw great success with some campaigns that required on-the-fly adjustments.

What started by offering a specific solution to a wide list of accounts in an effort to generate high-velocity appointments soon morphed into a more focused approach on specific accounts. By outsourcing to enlist the services of a dedicated SDR model, they were able to create extremely valuable appointments with decision makers across departments in new and existing accounts.

Read the full Tata Communications case study to see how ISS helped them reach previously inaccessible decision makers in global enterprises. 

Whether you’re adjusting to double down and take advantage of what’s already working, or recalibrating to achieve better results, remaining flexible through the enterprise selling process is key.



4. Experiment with Your Messaging

You may have found the Fortune 500 decision-makers, but that doesn’t necessarily mean you’re going to get their attention. Whether starting with an email, direct message on LinkedIn, or phone call, make sure your initial communication cuts through the clutter.

Keep your message short and sweet, stress their challenges and pain points, and reach out early or later in the day when they’re more receptive.

Time of Day graphic

And when you do land that coveted meeting with a Fortune 500 decision maker, be sure you completely understand the extent and cost of their pain, and how your solution provides specific relief. Far more significant in enterprise selling is your ability to build positive relationships with the right people in the organization.

If you’re not hitting the right notes at first, change up your content offers and educational materials you’re using throughout your sales process. Leverage testimonials, case studies, and prove the record of success your solution has among enterprise peers and influencers. And always customize each meeting and demo to speak directly to your prospect.

Can’t get past the “gatekeeper”? Here are some tips.

  • Sometimes despite our best efforts, starting the conversation with the gatekeeper is inevitable. Whether they are executive assistants or mid-level managers, always be respectful and be careful not to over agitate as you will likely be speaking to them multiple times for multiple personas within the organization.
  • Use your soft skills to get them to warm up to you, build rapport, and never downplay their importance. Especially in large organizations, gatekeepers can wield a lot of influence, so make sure to stress that by acknowledging their good work by saying things like “I know everything flows through you…”
  • Gatekeepers will be more familiar with their boss’s schedule and challenges than anybody else, after all, and they can be great resources in offering key insights.
  • But be careful not to divulge too much information — you don’t want them pitching to their boss on your behalf, or even worse, dismissing/blocking you from further conversations because they don’t think your solution is a good fit.
  • Just remember: a friendly, confident tone will take you far. If you sound like you’re making a call to someone you already have a relationship with, you’ll be much more successful than if it’s obvious you’re making a cold call.



5. Get Access to the Right Tools and Data Sources

Having access to an extensive database is key to enterprise selling. As we mentioned in our first point, the sooner you can get in front of the decision maker, the better. The good news is, there are plenty of tools to help charge up and streamline your enterprise sales process. Here’s a few we use at Inside Sales Solutions:

A lot of organizations looking to land larger enterprise accounts use an outsourced sales team to help with some or all of their campaigns. Sales partners like us come ready made with the resources and databases full of high-quality contacts to hit the ground running on the accounts you want to target.


Ready to Ramp Up Enterprise Selling and Reach Fortune 500s?

Engaging Fortune 500 companies and ramping up your enterprise selling is no simple task, but it’s made a lot easier with the right strategies and tools — and even outsourcing the services of a sales development team that tests, tweaks, and optimizes based on combined knowledge from internal and external teams.

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