Achieving Sales Success in the Enterprise Space

By | April 4, 2019


February 11, 2019


Enterprise Sales Success:

Selling to/for large enterprises can be daunting, challenging and completely defeating. Enterprise sales can also be highly rewarding, lucrative and provide longevity to a successful and prosperous sales career. Perhaps, you are new to the Enterprise Sales role, or you find yourself with a new compensation plan that includes aggressive growth targets. Or you may find yourself in the middle of a merger or acquisition that is presenting uncertainty or lack of clear sales territories, targets, prospects or customers. Any and all the scenarios outlined above are commonplace in an Enterprise Sales career. Expecting the unexpected and embracing the ability to adapt to change is a critical success factor in any Enterprise Sales role.

Spending over two decades in various Enterprise Sales roles with a handful of different organizations, I have been presented with some valuable insights and wisdom, along with experiencing the battle scars, losses and pitfalls to avoid. The first and in my experience, the most important attribute to foster is Mindset.


Developing, building and fostering the right mindset is critical to successfully achieving and closing sales to meet or more importantly exceed the sales goals required to attain the income/recognition or job security ambitions of an Enterprise Sales representative. Find and seek out the personal tools that will help your individual self with building a positive mindset. There are almost unlimited amounts of resources and tools available to help you sharpen this immensely important success skill. One of my favorite tools, I have used quite often throughout my career is “Creating Affluence: The A to Z Steps to a Richer Life” by Deepak Chopra Having the single mindedness of purpose and calm inner confidence will lay the groundwork for building yourself a successful sales franchise within the Enterprise space your assigned or targeting. Neglecting or disregarding the mindset will oftentimes lead to inconsistency in your sales numbers.


Key to building upon the positive mindset is a keen focus on alignment. Goals and Strategies are set at the top-level of most all organizations and cascades to each level within an organization. You will be challenged with multiple aspects and objectives, some seemingly competing with one another that need to be completed or met. I found it very useful to divide my focus into two parts; internal alignment with my organization’s goals and objective’s/mission’s and external alignment with my customer’s objectives and goals. Oftentimes, you will see that many of your customers goals and objectives are similar to your organizations goals and objectives. Focus your strategy and activities on finding those goals and objectives that align and build solutions, actions, resources and value around those aligned objectives. When a customer or prospect understands that you are seeking to build value and bring resources to help with their individualized goals and objectives, the relationship transforms into one of cooperation instead of victor/vanquished or winner/loser. Once you achieve this alignment with your customer/prospect, you move from merely being a “vendor” to a “partner”. At the partner level, price is of less concern and the overall value of the relationship is measured objectively.

Targeted Motions:

Ensuring your activities and sales motions are directed for maximum benefit is also very important to maintaining consistent sales attainment. This involves evaluating each and every tool available for prospecting, measuring and improving key metrics and ratio’s. Evaluate your pipeline ratio; and determine if your sales pipeline is at the necessary level to meet your quota. Look for prospecting tools both conventional and unconventional. Look at historical or enterprise wide sales data to see if your targeted or assigned customer has done business with your organization or a legacy organization and research the products and players. Look for additional “buying” centers beyond your traditional vendor management and build activity and motions around developing relationships by bringing value to others within your customers organization. Spend the focused prospecting time to insure a steady stream of prospects and opportunities to build your sales funnel. Re-focus on those opportunities each prospecting session to advance opportunities throughout the sales phase from pure prospect to a committed sale.

Another area to develop and foster would be internal relationships with sales overlay or sales engineering. Scheduling and maintaining a cadence with these type of internal resources will help shape your knowledge of your own companies capabilities but it is also a tool to help network and review shared contacts and prospects to further develop a broader base of potential clients or referrals.

Embrace the Culture:

Commonplace to most organizations, various Sales methodologies, training and techniques will be thrust upon you as you enter into an Enterprise Sales Role. Embrace these tools and methodologies and resulting culture to maximize your efficiency and productivity. One large organization, I am familiar with uses the Sales Methodology provided by ValueSelling Associates. Each sales team member is expected to have fluency in this process and each deal is discussed using the methodology framework. At one particular organization, if you fail to embrace this type of culture, you will not be around long.

Understand your results:

As your sales grow and your results begin flowing in, be sure you have a solid understanding of your sales compensation plan, how you are measured against the plan and look to exploit any incentives or promotions. As you achieve success and the sales are closing, keep a sharp eye on your results and commission statements. Look at your compensation plan and see if there are promotions, spiffs, concessions, etc with certain products, or sales “buckets” or solutions. Oftentimes, a simple add-on of a particular product or service, that would be purchased at some point anyway, could be the key difference in making a quarterly bonus. Diligently reviewing and evaluating your compensation plan for maximum benefit might be the difference between just making quota or making “Winner’s Circle” or President’s Club, etc.

Know Your Marketplace:

Always keep an eye on the competitive landscape both externally and internally. Be nimble and agile and ready to move with the market. As a solid performer in the Enterprise Selling space, and a track record of successful sales results, you will become a sought after commodity and will find another similar role with ease. Again, know your non-compete agreements and NDA’s you are under and avoid any conflicts of interests in possible alternative employment pursuits.

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