The first task is to make sure you are targeting a prospect that matches your target market. Hoping that you have what it takes to serve a large company, just because your solution "is a really good one", is not good enough. Your company needs to go through the process of matching their product roadmap, sales strategy and sales processes to the target market.
You should (for example) know that the targeted company is using SAP as an ERP system, but you also should know that they have not yet standardized on the specific SAP module that your software is a best-of-breed alternative for. If you do not have this information, you are wasting your time and your marketing department is not doing their job by focusing you on the proper prospects.
Assuming this has been done properly, you have now earned the right to knock on the door of that large Fortune 500 company.
How do you get your foot in the door as the sales rep?
If the aforementioned strategies were executed properly, the following should be true:
(1) You should be following up on communication that the prospect received prior to your call
(2) Your company should have completed at least ONE relevant industry activity (trade show, webinar etc.)
(3) You have the appropriate follow-up steps and material lined up
(4) You have a script as a guideline
Your role is to identify a friendly contact early in the process to start your journey. My advice is to start with someone that is involved in the subject matter and that is more accessible than senior leaders. Perhaps this individual is the legacy system owner. Or a subject matter expert. Trying to get in the door through the CFO or CIO, a Senior VP or VP of a department is an entire waste of your time if you are approaching the company for the first time as a sales representative. Talk to someone that wants to share some of their real-life day-to-day challenges in using the solutions you are targeting to improve.
Often the subject-matter folks at large companies attend trade shows, subscribe to industry newsletters, publish articles in trade magazines etc. so your marketing folks should have prepared you with that information. Alternatively, call and ask to speak to the relevant department. Here is an example of how you could speak to someone in the payroll department at a large company to get your sales process underway.
Rep: Dial the head-office or admin office for the company. Dial "0" to get the receptionist.
Rep: "Payroll Department please."
Receptionist: "Who do you need to speak to?"
Rep: "Sally Smith"
Receptionist: "What is this in regards to?" (Obviously, unsolicited calls are a huge problem for large companies - everyone wants to sell to them!)
Rep: "Sally is expecting my call - it's in regards to the payroll project she is working on. Thanks."
(If your company executed it's marketing strategies properly, Sally will take your call or she should expect that your company is relevant to them because your were given a lead that matches the prior situations that led to a deal before. Getting to talk to Sally the first time takes some creativity and persistence but you should never, ever lie. You do not want to start your relationship with a new contact or anyone else for that matter with a lie. Find an opening line that works for you and refine it. Remember, most large companies have some ongoing project activity - in just about any department.)
Rep: (once connected to Sally) "Hi Sally. I heard via the grapevine (could be one of the trade shows such as the APA we exhibited at) that your company is considering some changes to your payroll products. I am not quite sure to what extend you are making changes, but I want to let you know we have helped Company X and Y, who also uses SAP, to improve their payroll system performance. I am not selling you anything - I just want to make sure you know about us and will include us in discussions around the possible project. We are relevant, some call us "the next hot company", and knowing more about us can help you compile information that could be valuable down the line. Is this a good time for an intro or could I schedule another call when it's more convenient?"
Sally: "I have not heard about your company but I know Joey at Company X. I will ask him about your company." (Of course there are a multitude of different ways the conversation could go...this response illustrates the need to be ready for a call like this!)
Rep: "That's a great idea. Perhaps you want to ask him how our project manager, John, helped them cut 2 days per month off their processing time. Would you mind if I send you an email with some basic information our company though? In that way, you can have some more info when you talk to Joey. I am so glad you took my call - thank you. I promise not to bug you as you must be fielding hundreds of calls - but I do want to give you enough information so that we are included in any vendor evaluations."
That would work!
But only if some of the crucial elements were in place, such as a relevant lead from marketing, collateral, trade show presence, an actual reference at a large company, continuous exposure (mailers, webinars, trade publications.)
If you are a sales representative tasked to sell to large enterprises, you need to have the right environment established to enable you to succeed.