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      7 Tips for Selling to Enterprise Businesses

      Enterprise Sales to large and enterprise-sized businesses requires a different approach compared to small and medium-sized businesses. Why? Due to deal size and level of sophistication.  

      Only 0.32% out of 6,064,000 businesses in the U.S. qualify as large or enterprise sized businesses, according to the United States Census Bureau. They will also have more resources and money to spend, which allows them to be more selective.

      Every organization is different and understanding the process of how decisions are made and who is making them is crucial. In a large company, there could be multiple decision makers who may influence the approval of your deal. So, how do you get to the right decision maker?

      Chief Revenue Officer Interview Questions Here

      Here are 7 tips you can apply to get in front of the right decision maker and successfully sell to enterprise-sized businesses.

      Ash Wendt, Executive Recuiter
      Ash Wendt, Executive Recruiter

      1. Start with who you know

      Take inventory of the relationships you already have. Turn to your industry contacts, those you’ve sold to or tried to sell to in the past and let them know what your new venture is.

      If you have not sold to anyone yet, your goal is to get a warm referral to the organization you want to get into.

      2. Obtain your first customer

      Your first happy customers can serve as an advocate for your business. This is especially important for start-ups to prove that you are a real business to gain credibility and attract future clients and investors.

      Start smaller with small or medium-sized businesses. They will likely be your first paying customer to get your feet wet to eventually move up to larger and enterprise-sized businesses.

      3. Make meaningful connections

      Remember that real people are behind all businesses. Your goal is to make mutually beneficial and quality connections with these contacts to build trust. Be open and practice making introductions with vendors, partners, and even competitors. Find out how you can serve one another.

      A great way to do this is to participate in industry functions such as associations and trade organizations. You will get to learn about your industry and the people in it while becoming a regular contributor. Start by picking a few and plan on attending them in the years to come.

      4. Be the solution

      Instead of selling your product, sell a solution to the problem. You ultimately want to be the solution to the problems these large companies have. Be that trusted expert they call on when issues arise.

      5. Reach your audience through industry publications and media

      You can speak directly to your target audience through a variety of media outlets, such as industry publications, press, email, cold calling, white papers, and LinkedIn.

      Pitch to the right editorial teamsto get features in industry specific publications and become a content contributor to showcase your industry expertise. If people can learn from you, they will eventually start to see your company as a solution. Publishing white papers are also a great way to showcase your solutions through industry knowledge and real-world customer use cases to back it all up.

      Email is one of the best ways to connect with your target audience. Use your own list or rent lists from industry associations to ensure your emails get to the eyes of the decision makers you want to talk to.

      Furthermore, LinkedIn advertisements are a smart way to boost your digital marketing strategy. LinkedIn is made to target B2B companies so you can use it to identify specific regions, groups, and titles in your target demographic.

      6. Hire the right sales reps

      Sales reps are crucial to help find clients and mine new business from existing customers. To attract top quality salespeople, you need to support their growth.

      7. Prep a standard request for proposal document

      A request for proposal (RFP) is a document that is essentially an advertisement to sell to potential vendors on your services. Save time and effort by putting together a standard RFP package and update it quarterly. Then, you can easily reformat it to fit the entity’s requirements.


      There are many ways to approach selling to large and enterprise-sized businesses. In the end, it all boils down to connecting with humans and nurturing relationships.

      Need help identifying and recruiting exceptional sales talent with established Fortune 500 C-Suite contacts and histories of generating millions in revenue for their employers? Cowen Partners is a national executive search firm and has been featured in Forbes, Inc., IPOHub, Bizjournals, SHRM’s HR Today, Recruiter, and GatedTalent. Contact Us.

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