I used to hate enterprise sales, until I learned the most successful sales motions and sales teams are all about successful outcomes. If the product mostly does something value-able, and customer is taken care of, the money will come.

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).