Selling with Attitude

Oct 31, 2024

6 min read

Welcome to Selling with Attitude, a blog about complex, strategic, enterprise SaaS sales.

Over the last 10 to 15 years, maybe even more, I have noticed a distinct move away from large, enterprise, account selling. I am not really sure why, since these large deals are very valuable, sometime 50x the value of all those SMB and mid market deals I hear so much about. Probably because of the risk, uncertainty, and complexity. Starting my career in the 90's, the enterprise sale was all we had, and all we did, and all we were taught. Reps were properly trained and understood the risk reward of focusing on large accounts. I had my best year (400% of quota), in a year when I had 3 accounts, and closed 1. But now, with all the small SaaS solutions out there, everyone is talking about how to sell small deals faster and more efficiently.

So for anyone who wants to improve their ability to effectively focus and land large enterprise deals (> 200k ACV), I think you will appreciate this blog. Whether you are an investor, CEO, Founder, CRO, VP Sales, seasoned enterprise rep, or the up and coming sales rep who wants to enter into the big deal environment, I hope you will tune in. It is all about enterprise sales. If you are all into PLG (Product Led growth), or want to sell $10k deals faster, this is really not the place for you. Important topics, but not something I am focusing on here. I hope we will laugh, cry, and learn together. I know how freaking difficult it is to sell these big deals. I have lived it for the last 30 years.

To give you a taste of what we will do here, take a look at my favorite Dilbert of all time. If it resonates with you, keep reading, we will have fun.

I have certainly jumped through some hoops in my day, and now I want to help people take back some control in there accounts. Our prospects are not professional buyers of software. This is a nice way of saying they really do not know how to buy or evaluate a large purchase. Just take the RFP, a colossal waste of time for all concerned. We all intuitively know this, but time and time again, here we go. Answering 250 mundane questions that have nothing to do with value or selecting the right partner. Plus, I don't know the statistics, but I bet many more RFPs result in a no decision than a purchase.

So let's stop the hoop jumping and work with the prospect on a winning strategy. As we will learn and discuss in future posts, the most important part of the sales rep's role is to lead the prospect through a series of steps that will help both the prospect and the SaaS provider. This takes attitude. This takes a fearless approach. This takes credibility and rapport. Using the "walkaway" as a strategy to win deals, not to qualify out of them. (Oops, that will be a blog post in the future.)

So why do we do all these crazy things? Mainly, it is because enterprise sales is VERY HARD.

I have actually been in every role/function in a software company. I started in Development, moved to Product Management, to Marketing, then into Implementation Services, before getting into pre sales consulting and then direct sales. I even did a stint in accounting one year during my MBA. I mention all of this to make sure I let people know I respect and understand how hard all of these roles are. Every role has it's unique challenges and difficulties.

But seriously? The only people who do not agree that enterprise sales is the hardest thing to do are people who have never sold enterprise software! It is the least understood role in SaaS, as seen in comments like: those sales guys are so lazy, they just go out to dinners and win and dine folks, they don't understand how our software even works, sales is easy, just show them the ROI and they will buy, sales is a factory, you know, leads come in and ARR comes out.

Vista Equity is famous for some research that states there are 6-8 people involved in any buying decision. I learned this the hard way in 1994 when I lost 2 deals by thinking the department manager was the main player and decision maker in the deal. Turned out there were probably 5 other executives playing a significant role. I also think the 6-8 people rule is very low. For any deal over $300k in ARR, I bet there we get into the 15 people range, and that does not count the sponsors for the other projects that we are competing with for the budget.

The enterprise rep has to control the uncontrollable, figure out the agendas, personalities, and buying roles for all the people involved, and when asked a question, needs to understand the question, why they are asking the question, whether to even answer the question, and finally, how to answer, which is probably asking them a follow up question to their question. Tired yet?

Add to this the fact that corporations do not buy things, people do. And as we know, people are not rational. Or very forthcoming with difficult information. Ever try to get the real reason you lost a deal? Good luck with that. It is hard to get real feedback to the last demo you gave, much less feedback on how things are actually going in the sale. You will more than likely hear things like, you are doing fine, keep going (meaning we have some more hoops for you to jump through before we put this project on the shelf for another year).

OK, so you get it. Enterprise sales is hard.

To round out this introductory blog, I want to tease a few of my ideas for future blog posts. I have listed a few of the future posts below.

All the unhelpful (I did not say dumb) things I have heard and been told about enterprise sales. I alluded to a few of these above, but that just scratches the surface.

Why we underestimate how much pain has to exist for people to make a decision and buy software

Why you can't sell to a group

Why is it so hard to get to the truth

The 3 characteristics in every deal (people who know me will know this answer before the blog goes out)

Using the walkaway as a strategy for success, not qualification

Things we all do that puts us in the "sales schmuck" column

Having sexy indifference when selling

Putting the dead mule on the table (shout out to my friend David Craig for this one)

The lost art of the enterprise account strategy

There are about 50 more off the top of my head. I will shoot for weekly, but probably more like every other week, since this crazy hard world of enterprise sales has allowed me to raise 5 kids and now, go for a daily sunset walk on the beach.

The goal of all of this is to help and support the enterprise sales community. We all need support and understanding.

Who am I to write about enterprise sales?

As a 5x CRO and 1x CEO, I have supported or led 4 successful exits for close to $1B in enterprise value. All turnarounds with small to medium enterprise software companies. This was all hard work to figure out how to help that first group of enterprise sellers to succeed in tough, early adopter markets.

I have personally sold 7 and 8 figure deals in each of the last 4 decades, across different complex business applications (Supply Chain, Price Optimization, Asset Accounting, HR compliance, low code workflow, Revenue Management, and Fuel Asset Optimization), and different industries (manufacturing, retail, utilities, hospitality, convenience stores, finance, and others). The common theme was that they were all enterprise business applications that deliver very large ROI and transformational

I want to devote that next 5-10 years of my work life to help others sell better, smarter, and with attitude. Selling a million dollar deal is pretty damn hard, and most of the advice and information out there seems to go against most of what I have learned and experienced over the last 30 years. I would like to give back and help the enterprise sales professional and the companies that want to add large accounts to their target market.

Check out my profile on LinkedIn at John Huettel and my company at Lighthousesalessolutions.com. And you can subscribe to receive the blog directly to your email.