Two Truths of Enterprise Sales

Posted on October 27, 2023 Updated on July 19, 2025

I have been selling products and services to large enterprise organizations for most of my career. I like to tell people, “Everyone is in sales,” because one way or another, they are. 

Early in my career, I was a Systems Analyst for a Marketing company. I created what I’ve been told was the first custom coupon system for Subaru, as well as several systems for Mitsubishi Motors and Mitsubishi Electric. We would devise several ideas to pitch to the customer and then have follow-up meetings to flesh out the idea and help sell an extensive, multi-faceted program. It was a great learning experience in understanding what mattered and how to effectively upsell deals.

Standard sales advice is to sell to a known problem or a project. The thinking behind finding projects is that a tactical or strategic need has already been identified, with executive support and funding to address it. Most companies have some degree of dysfunction (which is why Patrick Lencioni’s books are so popular) that tends to affect projects negatively.

Focusing on problems is the way to go, but a business rarely comes to you to disclose those problems and their impact. A Consultative Selling approach is helpful in this situation. The upfront preparation can be time-consuming, but the results are often bigger deals that close in less time.

The process I use involves understanding the business, its customers, and competition, as well as potential changes to that business or industry. I will search for clues that indicate potential problems (from financial reports and filings to product-specific forum posts). I will then hypothesize about a few potential problems and reach out to the highest-level individuals in the organization likely to be responsible for these issues.

When you do speak with someone, you need to demonstrate your understanding and potential value add to learn more and begin gaining their trust while listening for validation or other information to refine your hypothesis. People buy from people they like and trust, and this approach becomes the foundation. From here, you can guide the process and expand your reach to other areas and layers of the organization. As a seller, your focus is on proposing real solutions that are mutually beneficial and have a high probability of success.

So, back to the two truths –

1. Companies and teams are often biased toward the status quo and the familiar. Problems are rarely solved using the same people, products, and processes that got them into this position in the first place. Your focus as a seller needs to be on outcomes. Help them visualize what success looks like and how it feels. Overcome negative emotions of fear using positive emotions and envisioning a better future.
2. Change can be expensive at first. It is an investment in the future that should yield both short-term benefits and long-term savings. Your focus as a seller should be on delivering value.

This approach and understanding can lead to new customer acquisition and ongoing account growth. You are continually demonstrating your value and commitment to your customers’ success, and that pays off.

Here’s a bonus third truth. If you cannot quickly gain consensus on the root cause problem(s) or traction with your proposed solution, qualifying out is often the best next step. Nurturing the prospect may lead to a future deal, but leveraging that 3-6 months on another prospect will likely result in more deals closed. Qualify out quickly and move on – that is better for everyone involved.

Remember, hope is not a strategy.