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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.




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