My Losing Battle with Enterprise Sales

He well describes the team of people that need to be involved in actually sending you a PO and payment(s): someone from purchasing, someone in middle management, possibly someone from legal, and the hapless folks who actually have to use your product. You never get them all in one room, which is probably a good thing.

The coach is the person who will get the deal done: they know the product is needed, they know who needs to be convinced, they can make the case, and they will sherpa you around to the appropriate stakeholders so you can make your pitch. Typically they are middle management for the people who will use the product, but they can also end up being someone who reports to the CTO or whomever.

Another key thing is go in at the right level. You might get an intro to the CEO, and she may end up convinced that your product is the greatest thing since sliced bread. That's unlikely to help: she'll come back from the week end and tell the GM of some division "hey, we should really be using that Foobartronix cloud solution!" and the GM will say "Wow, thanks, that's gonna make a huge difference to us" and then nothing will happen. You'll want to pitch the highest person responsible and no higher.

I once pitched our product the CEO of the Sony Computer Entertainment (Playstation). He was really interested and asked good questions and I assume forgot about us almost completely as soon as we had left the room. The importance of that meeting was that the other people who had decided to work with us (which happened in the blink of an eye...like 9 months) wanted him to know they'd found a good solution to a big problem. We were crucial, yet in an odd way irrelevant to that meeting.

I love love love the enterprise sale. It's complicated, strategic, psychological, time intensive, stressful and so many other things. Cunning, patience and integrity are key attributes that lead to success here and when you win, you win big. The key is to ensure this type of sale aligns with your temperament.

Years ago, a mentor gave me some advice (which I believe to be true): the key to selling to the enterprise is that you need to be known, liked and trusted.

To be known, you need to be getting in front of the key decision makers and influencers and build a real relationship with the long term in mind. There are no short cuts and salesman should not be writing an intro email or going into meeting 1 or 2 thinking (and pitching) like they will get the commitment on the spot. Skip steps and you lose the sale. It's a relationship that must be cultivated even after initial rejections. I can't count how many customers said "not at this time" that eventually came around to become large accounts.

To be liked, you need to be respectful, genuine and interested in them (not yourself). Find out who they are as people, what they value, what their goals are, their kids names. Ego is your enemy here. Read Dale Carnegie.

Trust is about integrity. You must believe in the product and the benefits you market must be realizable (that's not to say the customer will necessary place much value on those benefits). The moment trust is compromised, it's over (and not just for you, the company). It takes a sentence (perhaps just a word) to destroy a personal and company reputation.

Which goes back to the ultimate prerequisite (as mentioned in this article) of all enterprise solutions IMO - solve a problem that people care about.

Because the model is recurring revenue, elastic with workforce, and up/cross-sell, there's huge focus on account management, service levels, and delivering actual value.

If those aren't getting to the customer, it's likely they didn't actually need your product, or … their product didn't need _you_.

That's really the crux of the challenge. Vendors like Atlassian can win over an enterprise one seat at a time, and co-exist with competing tools in other departments.

But a solution close the hardware, like Puppet, is a company-wide cultural decision. There's a propensity for the enterprise to choose one winner.

There are some sales processes/books that get into this (Insight Selling, Let's Get Real, Ninety-Five-Five etc.) and really can open your eyes as an engineer that there is an ethical, effective way to manage enterprise sales to solve user problems.

Luke mentions Bladelogic. I worked for BMC for a while, and it rings true to me that there was a night-and-day cultural split between sales and R&D. Sales at Bladelogic under John McMahon were maniacally customer focused, similar to Mark Cranney's approach at Opsware (he's now at Andreesen Horowitz). BMC was run by Bob Beauchamp for many years, the ultimate salesman, and for all the flaws of that company, for many, they really cared about customer success, which explained how they could maintain $2B in revenue with aging, middling products. They just never seemed to be able to reconcile the cultural divide between R&D (which did whatever it wanted), consulting (which also did what ever it wanted), and sales.

The difference between a consultant and sales is that the consultant gets paid by the hour, the sales person gets paid by the success of the customer, assuming the incentives are properly structured. These incentives are, for example: subscription software commission, with an emphasis on renewals (i.e. lower pay on 1 year bullshit deals), maintaining customer satisfaction, and consumption, i.e. customer actually using the software, not it sitting on the shelf, is a good proxy for "they're getting value out of it".

I also find that enterprise sales generally requires a fairly intensive free consulting engagement called a "proof of concept" (POC) usually 1-3 weeks of intense work and commitment of time from both the company and customer to enumerate all the technical risks/benefits of the software, and to run through every single one of them until the customer (a) feels the product does what it says on the tin (b) can work in their political and technical legacy environment.

Getting to a POC as the last step before negotiation & deal close is a major theme in large enterprise sales motions, as it forces a crucible: users (not just buyers) have to learn the software, and their concerns are directly aired.

Sometimes POCs are poorly scoped and drag on forever, or worse, are inconclusive leaving the deal in limbo for months or years. This is where the better enterprise sales teams shine, as they focus on what will make the customer successful and address the concerns from the administration team and users.

I wouldn't underestimate the cost/benefit of sales. Sales execs make $250k+ OTE and the best ones top $500k to $1M or more with accelerators, because they have to coordinate across customer teams AND internal teams (support, consulting, R&D, sales engineering, sales desk, legal, procurement, etc.). AND they have to be personable and social. It's a tough gig. Sales engineers OTOH have to be a bit of a sales person in soft skills but also know 20+ years of legacy technology and IT culture along with the deep technical innards of a product to properly sell, demo, and POC it. On top of that, a POC takes several of them them out of other customers for 1-3 weeks, which is like $50k or more of investment alone. And after the first deal, they're often continuing to demo, teach, make friends, provide white glove support, etc., to make sure the customer stays happy with the solution.

This is why enterprise software gets expensive, into the millions, all of this high-touch time adds up.

Enterprise sales isn't something to avoid, it's still the nature of engaging with a large complicated company, or the government, where most of the users or technical folks aren't necessarily focused on the market, or upleveling their skills, they're focused on their internal problems. They need someone from the outside to expose them to the new ideas.

We keep thinking some next generation of knowledge workers will fix this, that everyone will be self-starting, self-educating, and will buy things transactionally with low-medium touch... we thought it might be the case with Open Source, and it hasn't (the biggest OSS companies have large enterprise sales teams). we also thought it might be the case with SaaS companies (but they too have large teams).

I empathize with his part on gear that sat there for years after the sale. Welcome to business, it happens everywhere. I've been on both the purchasing side and the selling side of it. Things just happen, just like we all mean to change the world or pick up a hobby but something else shiny gets in the way. But it's not a reason to give up on sales.

Politics are a part of everything. Engineers (or anyone) that refuse to accept this are just cutting their eyes out to spite their brain. If, on the sales side, you ignore the politics of the organization it is no wonder you struggle. The same is true for people in their own organization that can't get anything done, don't get promoted, or can't make friends.

Sales sucks. When you spend days, weeks, months, even years on a deal and you don't win you get nothing. Sometimes you even lose your job. Sales is expensive in more ways than just money or time and it is not for everyone.

I enjoyed reading your piece but the negativity in it is from frustration at lack of understanding. Just because you are not good at something does not mean it is bad or evil. I love basketball, but I am horrible at it, so I know realistically I will never be in the NBA. But because I do know what goes in to it I can truly respect those people that do. You can learn from others for things you are not good it, but why kid yourself? Focus what you are good at and become even better.

Michael Jordan was an amazing athlete, totally dominating basketball. He tried his hand at baseball and did decently but realized being just "decent" at it was all he would probably be and went back to what he excelled in, basketball.

I need to finish my book on sales and consulting geared towards engineers.

If you look around the younger generation succeeding in enterprise sales, you'll find that many come from a far more technical background. Maybe they transitioned via sales engineering roles first, but the next generation of field sales reps often have real world experience to apply in a consultative sales process.

The days of closing deals over steak dinners or on the golf course are over. Providing real business value in the short term during a quick POC is a must-have. Delivering on real business objectives over the first 6-12 months to ensure the expansion is too.

Some of the old guard, at least the ones that are any good, have adapted. A lot of the old skills are still useful for building relationships and trust. Being able to manage complex organizational challenges that getting more and more complex is an asset as well.

Great line.

It's a draining and frustrating experience.

The problem - as the author mentions - is that it can be so incredibly lucrative.

The author lost a lot of credibility to me when I read that part, because it’s often critical for the life and success of a product to be skeptical of customer requests or feedback, especially bespoke custom work requests that come up all the time in enterprise sales. Your company wants to grow and needs the revenue, but accepting custom requests takes you off-strategy and often wastes resources on things that won’t generate value beyond one isolated sale / renewal.

The Recurly founder had a great quote about this, related to why Dropbox succeeded (by ignoring feature requests from customers and imposing their own vision if a simple interface, and only adding features later). It’s discussed here: < https://zurb.com/blog/don-t-add-features-to-make-customers-h... >.

Anyway, this author’s rants actually strike me like someone who doesn’t have a good sense about product design or product management.

I simply don't have the moral fibre in me to fuck someone out of their money like a "b2b" guy does, or car salesman does.