Enterprise Sales 102 - beyond general sales

6 Apr 2023    

In Q1 2023, one of the scope of work is enterprise sales. While we perceive sales as a normal request for a favour from clients, that mindset will not set you up to succeed. In this article, as a way for me to merely articulate whatever i understood. Its not easy and its a learning process, you need to enjoy doing it.




  1. Listen to your customers

You need to listen to users in person. Even if it requires you to fly somewhere; even if you don’t really want to go.


  1. Learn your prospects’ business processes in details

Understand their process and understand how your product enhances their product.
If this is boring to you, you will fail.


You want to be perceived as a partner alongside them on the table, not opposite them.
Sitting opposite, you will always be kept at arm’s length, replaced when factors are not in your favor.


  1. Learn how your potential customer will excel in their companies through your product

How can you help the person buying your product’s career? While UIUX is important, you have to make sure the UX is providing value to your process’ champion


  1. Make, or don’t make, commitments to future development & features to meet their needs.

Your product will always be deficient in some fashion in the enterprise space. Always and forever.
Take a deep breath, understand (1) which customer persona are you talking to, (2) find the right bucket for this persona, (3) dig out whatever use-cases you understand from this bucket, (4) if this is new use-case, sit in and follow point (1), listen and understand how & why they are operating in this approach. Understand what constraints you have not previously considered before.


You will find yourself to be deep in understanding across the different buckets in no-time. First, you need to commit to understand their processes in point (2) & (3).


  1. You will learn how to not take no for an answer, how to beg for meeting, and how to ask for money and a check.

Its not intuitive if you have not done it before. It feels ‘bad’ when you have not tried to triple message someone across 3 different platforms: Email, WhatsApp, Linkedin.


  1. You will learn how to map out and sell to multiple stakeholders

The person you first talk to is rarely 100% in charge of the buying decision. Internally you need to manage and sales people, some great, some not, some won’t and will just take your money and prove to be extremely expensive


  1. You need to invest a lot of time here. From day 1 till ever.
    You cant just hire some magic “VP of sales” with 2-4 years of experience and have them scale your business without help. You need to first acknowledge the challenges & high level of context needed to execute in enterprise sales.

If you ever want to get deals above 3k Annual Contract Value (ACV), you need to learn to do most or all of the above.


  1. Learning how to pace yourself in your followups

You may not get an answer from your first message. You need to figure out how to pace your followup messages. See it as a structured relationship management. If there is no response, message them every 2 days.


  1. Learning how align your agenda along with theirs

Everyone is basically working for someone/something. If you are working, you highly likely have KPIs. If you have no KPIs set on you, you have interest you wish to further.


Find out what your stakeholders interest may be and you may see how you are more ‘interesting’ to speak with.




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