Enterprise Sales Strategy: Top 3 Tips

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Now is the time to set your enterprise sales strategy for the next year.  For many B2B software companies, this means looking at how you can transition from selling to small businesses or the mass market, to enterprise sales. The right enterprise sales strategy is critical for software companies that want to hit aggressive growth goals. While it is easy to grow a sales team that sells five $30k contracts per month to twenty $30k contracts per month, selling one $250k enterprise contract is a different league, if not an entirely different sport. Enterprise sales strategy is made even more challenging by the length of the sales cycles, you could be waiting 10 months or longer just to see if your strategy worked.


Although it may be complex, it’s important to take a methodical approach and do your homework first. Here are my top three tips based on my experiences working in a small company selling disruptive software to some of the biggest financial services companies in the world.


Marketing Drives Enterprise Sales: Content is King

Content Marketing and more precisely Thought Leadership, instill a sense of trust in enterprise buyers because it looks like your know what you’re talking about.


Drafting exceptional content is time-consuming and expensive, but it can make or break an enterprise sales initiative. Indeed, the biggest issue with enterprise sales is risk averseness. Any perceived risk can be a deal breaker. By drafting and marketing thought leadership content, your company will be perceived as a member of the elite, the “next big thing” and you will see readers both inside the target enterprise and outside analysts and consultants ready to become champions for you.


A Sales Process dedicated to failing fast

You need to build a sales process that qualifies leads very quickly up front and that adheres to a very narrow target. For example, if you want to sell in financial services to Chief Data Officers and you get CFO in Insurance on the phone, you need to say “no” and move on. You can’t afford to be distracted by “shiny objects” that don’t fit with your strategy.


You need a clear sales process where you qualify leads first and set aside leads that are not your target. It’s important to have the discipline to follow your process and strategy because it is only by following your strategy that you can test it to see if it works or not.


Enterprise Sales Strategy: Hire in Pairs

Always hire in two’s, as it allows the company to understand, if the results are not conclusive, whether the performance issues are due to messaging and process, or rather a problem with the individual employee. This is especially critical due to the length of enterprise sales cycles. If your sales cycles are 9 months long, you can’t afford to wait 9 months to see if your salespeople are good. Instead, you need interim objectives and at least two people working on the same thing to compare to each other. If they are both failing, then you need to look at your marketing, sales process, and message but if one is succeeding and the other isn’t then you have an HR issue.


There is no doubt that enterprise sales take time, effort, and investment. But the payoff for software companies is huge. Once you start signing big names to large multiyear contracts, you enter a different league of software companies and your valuations will rise massively. So as you look at your plans for the next year, take some time to reflect on a clear enterprise sales strategy and be prepared, at least at first, for the majority of enterprise deals to be managed by the leadership team and for those deals to take at least 6 to 9 months to close.    

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