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Enterprise Sales Guide: The Process of Selling Enterprise Software Demystified (enterprisesales.nyc)
257 points by mickeygraham 933 days ago | hide | past | web | favorite | 66 comments

I'm in technical presales and have been in and out for about 10 years. It's a very rewarding career, if you like socializing and are particularly interested in tying your individual/team efforts with your pay (vs. the RSU/option lottery).

These are all good articles, though I'd particularly point to the a16z articles and Ben Horowitz' book "The Hard thing about Hard Things" for an appreciation of what sales brings to a company that needs enterprise customers.

Also, sales can be learned by anyone. Some of the best sales people I know (earning $400k most years to upwards of $1m in a year if they hit a home run) are deeply technical.

Do you have any suggestions for what approach someone who's "deeply technical" should take to move into something like technical presales or enterprise sales in general?

It's a potential career transition that definitely interests me, I'm just not sure where to start. Getting to talk (& teach?) potential customers along with tying pay directly to performance are both very appealing elements of the field. Any additional advice appreciated! Thanks!

I was a developer for 17 years and switched into enterprise sales a couple of years ago (with a short stint as a technical account manager in between). The upside of the transition is that sales is still a job for problem-solvers, although you'll be much less hands on. The downside is that there are expectations for performance that come along with the upsides of being paid based on that performance. I still hack on stuff in my spare time, but that time seems much less abundant now (certainly less time to surf HN, for example ;)).

If this is something you're interested in, many organizations are in need of sales engineers (pre-sales technical folks) who have real experience from the trenches. If you are comfortable talking with technical and non-technical people alike, sales engineering is probably the best place to start. The challenge with getting into a purely sales role is that many places expect a level of experience before hiring people. Negotiations and proposal building can be surprisingly complex, and there aren't many organizations interested in training-up sales people. Sales engineering would serve the purpose of giving you exposure to the pre-negotiation piece of the sales process, as well as introducing you to a lot of people with deep experience in the negotiation / closing process.

I'd be happy to chat with you offline about my experiences as well -- my email is in my profile.

I've done pre-sales despite not being on pre-sales pay before for a short time after all our pre-sales guys quit pretty much (long story). But the biggest thing I did to get to that position is to be involved and care about what your customers are doing with your product. Be indispensable to your sales demos and POCs. If you become the go-to guy in your engineering team, you have an edge already because most sales and engineering orgs are so divided from each other you'll be in the know rather soon.

I started down this way because while I love technology, I was getting pretty bored with the typical engineer personality types in every company I went to, and I was starting to get a little heat for being too customer focused. This makes sense when your company is at risk because they're drowning in features while engineering is light years ahead and into YAGNI territory. But simply caring beyond your engineering duties of ship stuff on a schedule is a huge step in mentality.

> I was getting pretty bored with the typical engineer personality types in every company I went to

I know what you mean, but I haven't given up yet. I still can't believe that a field this dynamic and intellectually challenging is so devoid of... personality and wit?

Its probably different in the valley, but this has been my experience in Europe. After 7 years, I still don't get it.

From my experience, engineering is intelectually challenging in a very narrow sense - you tend to use a few core skills over and over. Even when you learn a new paradigm, like functional programming, it's still within your comfort zone. It takes serious psychological effort to peek out of your hole and be willing to learn about a truly foreign subject, such as sales.

Besides that, I'd bet that a lot of programmers suffer from social anxiety (I used to be one of them), which severely limits your ability to express any personality that you might have.

Yeah, but! You could say most of these things about sysadmins, and some of them were the funniest guys I've ever met.

I think the fact that these stereotypes even exist means that there could be a biological reason behind it. Levels of dopamine and serotonine in the brain, the amount of muscles, a lean or a broad frame, social anxiety,...

These things interest me a lot, mainly because they affect me as well of course, so if there is a place to discuss them I'd love to hear about it. Actually I'm surprised this isn't a regular HN topic .

To be an effective sysadmin, you have to be able to work well under pressure. If you have anxiety, you will definitely not work well under pressure, so programmers and sysadmins have different personality traits, methinks.

Regarding biological reasons, you might be interested in the Human Behavioral Biology course [1]. I'm half way through it and it's jam packed with knowledge.

[1] https://www.youtube.com/playlist?list=PL848F2368C90DDC3D

Programmers have to program under stress on occasion for fixing or shipping stuff rather quickly before, say, a meeting with VCs. But this is where the sysadmin / execution-focused folks will perform better on what would seem to be menial tasks because most programmers are so used to controlling their work environment while sysadmins and network admins are oftentimes running under tight "get it done right now" situations.

I've hired a couple guys for my ops team that are primarily developers because I want a more forward-thinking and feature development pace for the work we do, and just plain better forethought would cut these stressful scenarios down to maybe half an hour of troubleshooting instead of hours and days.

Well this will consume some of my evenings, thx!

It depends very much from company to country and so forth, but I've worked in the U.S. for over a decade now across both massive and tiny companies and the best way I can put it is that if your engineering team can fairly neatly fit into the different engineer stereotypes that are in the show Silicon Valley or the IT Crowd at least 80% of the time, you probably have selected for a rather narrow spectrum of people.

There are a great deal of very intelligent people that cross so many different ranges across humanity and IT / software seems to select for just a small slice of the possibilities and the richness that exists. Even among companies you are biased for certain personality traits (big companies tend to attract those that are less risk averse or with children due to the 9-to-5 culture as stereotype and vice versa with smaller companies).

The European immigrants I worked with certainly had a different sense of all sorts of things as well as the Middle Eastern and African immigrants. But gosh do they all share some strange similarities despite all these differences.

Things do get rather boring potentially outside the usual nerd crowds. For example, I really don't care about following competitive sports - this is a huge, huge social handicap in the U.S. even among women in many regions. This becomes even more pervasive among sales folks for sure - I think most sales folks that are pretty good performers are actually pretty darn.... moderate if we tried to "average" personalities. It's clear among managers that engineers tend to be a rather specific group of people that doesn't necessarily need to be accounted for among other types of organizations.

Another recent convert from Dev to Sale Engineer here...

The thing about bonding over sports is one of the first major differences outside the tech social circle.

I would agree on the statement that it is an advantage to be following sports. But a recent trend in companies is a more diverse hiring pool because decision makers are become more diverse as well.

I also think the end goal of bonding over sports is being relatable and likable. If you have other traits that compensate for lack of sports knowledge, you can still be successful.

> Things do get rather boring potentially outside the usual nerd crowds

Yeah that seems to be the case - or at least the challenges are on a different level.

The thing about competitive sports: I've found a good way to handle it is to be very firm and confident about not being interested in it at all, thankyouverymuch. Just brush it off in a non-awkward, humorous way.

Here's the thing, you might be able to side-step the issue, but when your competition's sales guys chat about the NCAA finals hopefuls, team composition, coach histories, and certain rivalries and you can only comment a little bit at the dinner after your demos, the customer will remember more levity and just plain fun about the other guy than you when it comes to the emotional side of "which company has reps I will have more rapport with?" Think of it similar to dating and trying to impress a few girls - without a sense of humor you are at an immediate disadvantage. This is what most engineers outside sales would think of that golf course meeting or something, but it's all about establishing something more than just a one-time transaction relationship - it's going to continue, so it's not far off from the dynamics of dating aside sexual part. But consider for a moment that everyone is on even footing in a dating pool - the one that is most memorable and associated with good feelings where you let yourself be vulnerable will win.

Enterprise sales is complex but still fundamentally rather emotional among the decision-makers. The kinds of companies that buy $10MM of software in a year from one vendor are only so many, so there tends to be reputations that follow people, and many sales persons simply follow along a few friends that are executives at organizations across their careers and sell whatever software they're peddling every time they switch companies.

Yes that is of course very true. Sports is a helpful topic (just like the weather), but there are so many other things to talk about, and ways to be a memorable and entertaining business partner.

My experience is that sales people are not actually liked all that much, as their efforts to socialize sometimes seem forced and creepy. You can turn that into your advantage.

I simply am genuine in that I do like to talk about all sorts of things by nature - sports included, but because I'm not the most versed in sports history and just don't follow (I care about baseball and basketball about as much as I do Star Wars and Star Trek, so I have to pick carefully). However, I've managed to learn while giving a bit of an ego boost to people I meet just asking for their opinions on stuff (I do care, I'm just looking for data constantly, especially ones combed through by SMEs of any sort). Ask some sports nut to explain a few simple things and they'll react a bit like someone that humbly asks a developer "So I don't know much but could you explain REST to me?" Nothing wrong with enjoying some company that might be a lead, it usually doesn't hurt, so why not have a good time and possibly lead to a ton of money?

> I still can't believe that a field this dynamic and intellectually challenging is so devoid of... personality and wit?

The stereotypes, as usual, do seem to have some truth behind them.

I've lived with, worked with and hired engineers who behaved like machines, treated conversation and pleasantries as a waste of time, and some who existed in their own subculture. Perhaps they were full of personality and wit in their subculture, but in my experience... no.

This is Europe too.

Sales engineering is definitely the place to start, the requirements are (a) technical ability balanced by (b) an ability to communicate clearly and (c) listen to customers and/or get them to talk about their problems, and be able to map them to your software's capabilities (or to know right away it isn't a fit and point them elsewhere).

A good sales engineer is a "glue player", in that they do a combination of: - Presenting the company, or products, or concepts/architectures to prospects customers and partners

- Demoing products and concepts that illustrate some kind of meaningful benefit for the audience rather than just "this button does X"

- building technical champions in your accounts - taking people out for tea/coffee/libations , lunch and learns, listening to them, white boarding with them, basically teaching them to sell on your behalf at their companies because their jobs are easier if they have your product

- Qualifying and scoping opportunities with your wingman, the account manager. This is figuring out what the customer needs, if you can fill that need with your software, and what is missing.

- Scoping and executing a proof of concept, which is half engineering , half performance art. Basically it's about validating to a customer in a time boxed project that they can achieve their goals with your software

- On site customer support, when the support line isn't enough

- On site architecture / solution support, when post sales consulting isn't enough

- Sometimes crafting quotes, deals, and proposals though often this is in the account manager's wheelhouse

Good books on solution selling (ie. Focusing on customer success rather than "dumping the license keys and running") include "Let's Get Real or Let's not play" by Khalsa and Illig or "Insight Selling" by Schulz and Doerr. I also recommend a course or book on building good presentations such as from Mandel Communications.

If you can demonstrate technical and presentation skills in an interview and give a good demo (record yourself to practice), you'll likely get an SE job. Your comp will usually be 70/30 or 60/40 fixed/variable and you'll be comped based on your region's sales performance.

From there, the next step after a few years is to sales specialists (basically a sales account manager specialized in a product area) or account manager (general sales rep). These pay more variable comp (60/40 or 50/50), lower base pay, but strong accelerators after you hit your quota (this is where you hit $400k+). This requires knowing sales processes and building relationships with sales management that you'll gain as an SE. Some companies aren't great at growing their SEs into reps, some are - jump elsewhere after a couple of years if you're stuck in a "hey geek give us a demo" transactional relationship with your sales team.

Once you get into pure sales, it is way more about deal structuring , relationship building , managing your support network (SEs, consulting, support, proposal building, field marketing) to focus on your accounts, and relentless repetitive discovery and qualification of needs - and being able to be rejected a lot without getting depressed. Technical stuff takes a back seat though still is helpful for credibility and bullshit detection. It's not for everyone (I don't think I can do it, but never say never). But the upside if you're good at it or at a growth company can be high.

As someone on the implementation side I have a sour taste for Sales and Sales Engineers. Always selling features we do not have or things we cannot do. Then they mock it up and leave and I have to break the news to the customer.

You may wish to consider your sour taste to be less targeted at Sales and SEs and more around (broken) company-wide processes and (lack of) clout the implementation teams wield.

I'm also on the implementation side (sometimes referred to as professional services), and two immediate thoughts jump to mind:

1) Unless you're a practice manager directly responsible for maintaining a targeted book-to-bill ratio or other quota metric (which usually entails account and long-term customer relationship management), your management should not be throwing you under the bus and exposing you to break that news to the customer. Nothing destroys a booking pipeline faster than customers with mismanaged expectations.

2) This type of behaviour from Sales teams is usually indicative of misaligned incentives. A concrete example of this type of situation could be company in an early "hyper-growth" phase where they only comp on new bookings, and don't comp Sales on contract renewals.

Much of the time sales' over-promising comes as a result of some management or client services functionary that's not a technical product manager but thinks they are insisting that $requirement definitely will be possible once $feature is in place, which definitely will be on time, so no need to communicate with the dev team at all on that.

(It's often the same middle management that omits to let the dev team know the system is supposed to work on IE8 until the client complains.)

Sales commmonly direct their sour taste towards the developers...

Is it common for managers to actually get involved in projects in other organizations?

I had a long response written out but my browser barfed. Short answer is "yes". Longer answer is "it depends" on the size of the budget/deal, the business function that the manager fulfills, and the size of your organization as a whole:

* Business function: If you're customer facing, most [project|practice|field|support]managers should be sticking their nose into day-to-day projects, especially when a bad message needs to be delivered (e.g. the product we sold you will fall short of your expectations). This is not only because the customer will be incensed, but because there may also be commercial repercussions (e.g. SLA penalties) that you may not be aware of in umbrella master [service|support|license] agreements.

* Deal/budget size: Typically, the larger a manager's deal or budget, the more headcount they have. And the more headcount on a project|team|division, the more intermediate managers there will be to layer the manager in question. Hence, if the deal size is rather large, in most cases managers will not get involved on a day-to-day basis, but should be available for escalations (presuming an account management role for larger deal sizes). If the deal size is usually smaller, more than likely the manager will be more involved (e.g. as a project manager).

* Org size: BDC - not usually. Startup - usually yes.

A lot of it is cultural. Is sales job to hit the number, or is it customer success? It has to be the latter if you want to grow a reputation and in turn increase the level of relationship with your customer. This is the difference between selling a $400k one off, a $2m "mail the CDs and run", or a long term relationship that nets you $10m or more and multiples of that in benefits for the customer themself.

Also, some (most) places do not have very good lines of communication between sales and R&D, while others do. I'm lucky to be in a place where I can submit a PR on Github if I need something yesterday, or can file feature requests / fixes that will get looked at within the week.

My view is generally that the relationship with a customer is where you make most of your money over 5+ years, selling them an opportunity once by promising the moon and delivering a paper plate is in no one's interest. Lots of sales people act that way but that's not going generally going to be your leaders.

I'm a Sales Engineer and I work mostly on the post-sale implementation side of things, which is not really a common approach - so I completely understand why people feel this way. One of my main jobs is to keep our Sales team informed of exactly what is and isn't possible, because most of them just don't know better when it comes to deep technical topics. Having somebody on the Sales team who is willing say no is really important.

I've been on break/fix and on the Sales Engineer side and know both - there's never a single side to these things.

Sales Engineers in particular don't want to sell something dishonestly - it opens the company up to risk and it hurts their credibility, particularly if you sell multiple products.

There are a few reasons I can think of:

1. The technical people that run the current implementation didn't put their requirements into the sales process.

2. Some of those features really don't matter to the business and were fodder.

3. The requirements were listed, but not accurately or with enough depth.

4. The Sales team didn't have enough knowledge (or training) to know the difference - or inaccurate documentation.

5. It was roadmapped close enough to implementation and including delays to go ahead anyway.

6. The competitor claims to have this feature but theirs is broken also, so it's a race to who can sell broken stuff faster - because nobody can truly do it.

The people and the companies that support this exist certainly - just not for very long.

I see different incentives within my own organization. Sales and sales engineers makes commission so they want to close the deal no matter what. I deliver a specific product so I just want to get it done and stay under budget. Another consulting group handles the long term customer relationship so they are more inclined to give away free work for future relationship building that I am not incentivized to want to do.

Interestingly, one of the A16Z articles in this collection cites the need to sell "future potential"; not what's available today.

> Always selling features we do not have or things we cannot do.

Oh, hey VMware! What's up?

I'm sure you could insert any of the big software companies

Working in an enterprise and having bought enterprise software, my suggestion to the sales staff would be: Learn to say "no"!

If we send you twenty pages of requirements, we do not expect your product to cover each and every one of them (especially not those labeled as "nice to have", and also not those that were inserted just to please some internal egos and will be ignored in the decision-making altogether... although I grant you that this will be hard to judge from the outside). Nevertheless, I have experienced time and time again that sales agents waste 45 minutes of their two hour presentation to try to explain some clumsy workaround for something their software cannot do instead of spending that time to focus on what their software can do. Also, a software that supposedly can do everything makes me wonder if it can do these things well... or if we might end up with a solution so customized that every upgrade turns into a nightmare.

I was absolutely expecting this site to be satire. In my experience, enterprise sales involves building a great demo, lying through your teeth and cashing the checks.

It's gotten better. Standards are better now.

But a big chunk of enterprise sales is just learning to understand the customer's organization, how it works, how it makes decisions, and what problems the customer is experiencing. Part of the reason things are so expensive is that the sales cycle is so long and arduous, and that's because it's just really, really hard to communicate and make decisions within large enterprises - even when they really, really need the product and have strong internal champions.

> It's gotten better. Standards are better now.

> learning to understand the customer's organization

I wish this was the case all around, clearly it happens at least occasionally or you would not have your personal experience, but I have yet to see it in mine. If I have seen it, it was so well executed I didn't even notice, but even then from my experience that is the minority of cases.


I went from performance work / data science tools at Facebook to PM at MemSQL. A big part of my job is enterprise sales engineering (SE) work, pairing with account executives (AEs) around the country as we fill out our SE team.

The funny thing is that I'm doing much of the same things here as I was doing at Facebook: understanding the team's core problem, understanding their systems, designing benchmarks, explaining possible solutions, walking through operations scenarios, etc.

There is more PowerPoint time, as we are from a separate company and need to establish our credentials first, but the bulk is deeply technical and the standards are high. I couldn't bullshit these people even if I wanted to.

Younger people who were more technical in the early 00's are not moving up into management and decision making positions in companies (buyers). It's requiring a more technically savvy sales force in return.

The market is providing.

Agree completely, although this does seem to be changing depending upon which verticals a company is in.

this is an antiquated point of view.

I have seen it with my eyes in the last 6 months and it seems to be a model that never stops working. I'll specifically name Adobe, HP and Oracle as offenders. There is only 1 sales model I'll accept. A 30-day limited developer license to install/access and tinker with your product. Maybe companies exist that are "doing it right" but the old way is still alive and kicking and raking in millions.

EDIT: Exhibit A-Z is the current $240M lawsuit by the State of Oregon v Oracle: http://www.bizjournals.com/portland/blog/health-care-inc/201...

Any sufficiently advanced technology takes more than 30 days to customise, never mind decide it's the optimum solution...

It's not a matter of building out your entire project, it's just to get a feel for the quality and decide if it's complete bullshit. If you think 30 days isn't enough time, then a vendor demo is worth less than zero.

As an enterprise software developer, who gets pitches constantly from stuff we "need" I'd love to hear this elaboration

I have first hand experience that says it still happens.

Go on.

I was expecting an actual article.

Haha me too, I was like geez I hate those guys, they come in in teams of 4, the only reason we're listening to them is because they partied with my boss,

Grill them, a year later sign up for something we 10% need lol

it must be frustrating for you to be so much smarter than everyone, yet still be unable to make any decisions.

The reality is that folks like "the_falcon" are the main reason why the sales cycles are longer. If they wield any amount of technical sway, it becomes orders of magnitude tougher to close a sale when they lay down deliberate & contrived (test) barriers. Oh, and they love using the POC technique to waste your time either solving their problem for free or finding out that they didn't really have their requirements fully understood.

Coming from the other side, the reason the POC is so important is because the reality is that we need to get the tech into the hands of the engineers so they can implement it, break it, and then run it for 6 months and troubleshoot it before they know if it's A) any good to begin with and B) a good fit for the problem they want to solve, and they have to do that with your product and whatever competitors are nearby in the Gartner MQ.

I know the sales guys work for their money, but I don't think the above is alot to ask for what could potentially be a quarter of a million dollars in recurring annual revenue.

By the way: The Sales subreddit has some very good information regarding sales. A good amount of knowledgeable people visit it. They've helped me before to get over my self-inflicted sale issues (due to my introverted nature).


Do you mind linking to the thread where they helped you? Sounds like it'd be very useful to me too.

I'm afraid of asking questions publicly, so all is done through PMs. Most people will gladly answer and help. I find helpful people by combing the most commented on threads and reading the answers. Thoughtful answers tend to be written by people with a sincere desire to help. I don't usually ask the same person for more feedback to respect their time. To get the best advice ask actionable questions. Like "I'm using this this email script to land cold leads from small businesses. People are not replying much. What call to action can I include to get replies?"

I'd like to hear about that too.

There's a lot of SaaS articles in an Enterprise selling article list. I'm curious how many SaaS products have broken the Enterprise market that people know of? And by Enterprise, I mean at least 6 figure annual price tag, not a few sales to 10 person teams that happen to work within an Enterprise. I guess Google for Work and Salesforce are two...

ServiceNow - ITSM / ITOM Workday - HCM / ERP NetSuite - ERP, Commerce, CRM


The incumbents they've displaced are insanely horrendous pieces of crap (I will name none of them) and as a technical person they are all light years ahead. People that badly implemented a previous technology stack are likely to mess it up again though (see CMDB implementations). SOAP services that at least kind of work are even a god-send in this market let alone something resembling REST. The sales cycles for these stacks previously were so long that entire generations of software came and went along with architectural patterns.

The list is very long. HR applications across the board are generally very expensive, so you'll easily hit six figures for a business with just hundreds, not thousands, of employees.

This is why the exciting new breed of start-ups in this space (payroll, ATS, HRIS, etc) are making a killing—amazing profit margins, even when you dramatically undercut the established players.

Especially when the established players:

1. Have huge bloated software that is hard to add features to, support, or reason about

2. Are based on a decade or more old software (at best)

3. Are being undercut by software that does probably less than 10% of what they offer, because nobody needs the other 90% of shit they pack in (but did because they added some customization or "feature" to the product whenever a big client came online due to some slimy sales guy)

The beauty of all the macro trends in the enterprise right now (cloud, big data, BYOD, etc) are that they're not just buzz words. They've been forcing functions for large corporations to move off legacy incumbents who can't keep up and to leverage startup tech across all areas of their business and IT infrastructure.

Check out www.work-bench.com/startups for a list of a bunch of companies selling true enterprise-class deals and doing a great job at it.


This article by Steve Sinofsky provides a broader framework to understand Enterprise sales.

Very interesting.

lol, enterprise tech sales needs a guide?

1) Wear douchy leather shoes, slacks, look smart 2) BS and make stuff up on software you 20% understand until the client nods 3) Keep going 4) Call client, every, freaking, month, for 2 years 5) Do this enough - Sale!

ha ha! I get it! Cause the job title you have determines your personality and style and ethics and morals. And all sales guys are slimy, not like us pure, rational engineers.

1. Go to expensive golf course, 2. Propose large software purchase, 3. Large envelope stuffed with cash, 4. Profit! Rinse repeat.

haha I said almost the same thing above.

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