Enterprise Sales 101
Lessons learned from Kevin O’Brien, CEO/Founder of GreatHorn
One of the best sessions during the Techstars program was the Enterprise Sales crash-course provided by Kevin O’Brien, founder and CEO of GreatHorn, a cloud-native email security company for the Fortune 500.
Here are some of my key takeaways.
First, it’s worth clarifying exactly what type of sales process we’re talking about. In B2B sales, there’s predominantly two camps: the SMB sale and the Enterprise sale.
SMB sales are generally volume/transaction based. Companies pursuing this strategy are likely trying to build a process that is somewhat self-serve or automated, as the ultimate user tends to be the buyer, so they can easily just punch in their credit card to sign up. A good example of this is the increasingly popular service Calendly, as anyone can basically just sign up and get started (i.e. there is no lengthy evaluation process).
Enterprise sales, which Kevin’s presentation predominantly focused on, are a different animal. They revolve around larger organizations with multiple points of contact. Sales conversations where you never really know who’s on your side and who’s not. Most often there is a proof-of-concept or proof-of-value phase that you must go through with an enterprise, during which the enterprise will demo your product before making any form of financial commitment. Sometimes the team tasked with qualifying software vendors are completely siloed from the ultimate buyers by design (in some instances, they may not even be permitted to know key details such as pricing to avoid bias). Further, enterprises may have strict policies on engaging vendors, such as soliciting multiple bids and engaging multiple providers.
Obviously, these sales processes are longer and harder, so why go through them? In the end, they tend to be where the most value is, so they’re almost always worth the pain.
With this background in mind, Kevin laid out 3 key questions at the core of a sale that every seller needs to answer for their enterprise customer:
- Why should I do anything?
- Why should I do it now?
- Why should I do it with you?
If you can answer all three questions, typically you have a good shot at a sale.
Why should I do anything?
This is probably going to be the easiest question to answer. Typically the reason is that your product will either 1) make the customer money or 2) save the customer money. In other scenarios, there might be regulatory or compliance reasons that oblige the customer to purchase software like yours.
Why should I do it now?
Ideally there is some cultural moment that plays to your product (e.g., the virtualization of the workforce due to COVID-19), but if not, answering this question will be somewhat of a function of your customer discovery process. As a salesperson, you are trying to ask questions that help the customer realize the “why” behind a particular pain point they’re currently experiencing. Show them something that might intrigue them — you’re trying to elicit a “tell me more” response.
Why should I do it with you?
This question is probably the toughest of the three, as your customer will most likely have a variety of options at their disposal. Presuming you’ve advanced the conversation sufficiently, that you’ve peaked their interest towards doing a serious trial or pilot of the product, Kevin recommends that a great way to sell the “why us” answer is through a highly detailed pilot management plan. AKA “Show, don’t Tell.” Through showing the customer exactly how a pilot process will run — such as what stage of the process you’re currently in, what are the next steps, what are the next steps after that — you immediately convey that you are a knowledgeable, reliable, organized company that will be a truly value-add partner throughout an important process wracked with several unknown’s.
Best Practices
One of the key takeaways that Kevin stressed is the importance of implementing a simple, but rigorous process when it comes to tracking sales pipeline progression.
For starters, the sales team should be beholden to a formalized process and be able to answer key questions about the deal prospect. Kevin uses the mnemonic MEDIC (Metrics, Economic Buyer, Decision Criteria, Decision Process, Implicate Pain and Champion), but there are of course others. Without answers to these questions, it is likely an unwise investment of time and resources to pursue this sale much further.
Second, it is essential to log all sales and marketing information in the right systems. Salesforce is the gold standard for a Sales CRM, and any good salesperson you’re seeking to hire will expect you to use it. Hubspot and Marketo are similarly the go-to systems for Marketing. As Kevin said in his presentation, “If it’s not in Salesforce, it doesn’t exist!”
Sales teams should have weekly pipeline review meetings to assess and re-assess what’s in their Salesforce system. As Kevin noted, “You should continue talking about accounts, why they’re in the system, and how they’re developing.”
Finding a Champion
One of the key points in Kevin’s presentation was the idea of finding a “Champion,” or someone who will help the sale succeed internally at the client. There are three key personas to be aware of in an enterprise sale:
- Champion — someone with direct access to the buyer
- Coach — someone who can connect you to a Champion
- Blocker — someone who doesn’t care/doesn’t want the deal to happen
It is rare that the Champion and the buyer are the same person; more commonly, the champion will report to the buyer in some capacity. Another salient piece of advice Kevin offered, is that if someone in the room hasn’t said anything throughout the course of a presentation or pitch, it’s highly likely that they are the blocker!
Final Word
Overall, I thought Kevin’s presentation was a highly illuminating discussion of how to sell to enterprises and build a culture of success internally at your company. It is clear that diligent record keeping and a methodical, systematic progression of client relationships are key to winning large enterprise deals.
For more information, Kevin’ has offered various forms of advice across a series of podcasts — go check ’em out!
