In 2021 my career was a Toyota Camry. Reliable, not particularly flashy, and my butt-shape comfortably embedded in the seat. I was doing software development on the mobile apps at RxSaver. Nothing wrong with the Camry club, but I decided to trade in for a 4-wheeler and steer onto the dirt path of sales by joining Bitrise as a sales engineer (SE). Three years later, I’ve got no regrets, but I do see that my technology skills might be receding in the rear view mirror. And that is a threat to my survival as a sales engineer.

What actually sells

I’ve learned that the best way to win business is to be an expert in the technical domain of my buyers.

Bitrise is a continuous integration product. The purchasing decision is rarely made by the CTO or CIO, and the key selling event is not a slick presentation or a steak dinner. Instead, leadership at the buying org is usually looking for a senior engineer (or group of them) to give them a thumbs up or down on the technical merits of the product.

In an engineer-led evaluation, I’ve observed two primary hurdles that the sales engineer’s got to get past without falling on their face. First is earning the proof of concept (POC), and second is successfully executing the POC.

Usually, before ever talking to sales, the evaluator has already read the docs and even secretly tinkered with it by opening an account using their personal email. If I’m delivering a demo to a prospect, a good signal is when an audience-member takes me totally off script by asking hard, specific questions. They already know the basics, and they are checking that we can handle their esoteric requirements.

Jumping this hurdle doesn’t require I have an answer to every question. However, it does require that I am knowledgeable enough to pass the “Is this guy bullshitting me? Can this actually do what he says it can do?” test. That test is only passed by proving strong knowledge of the technology domain. Doing so indicates that the POC will probably work and is worth the time that will be spent.

At POC stage, the evaluator is going to put the product through its paces, and they will find gaps (no product is perfect). My goal is to score as high as possible on the evaluation metrics. This often involves creative workarounds like opening PRs to fix/improve a small piece of the product, writing a custom integration, or deep-diving into the prospect’s app’s build process to fix errors or eliminate performance bottlenecks.

Prior to doing sales engineering, I spent 10 years doing iOS, Android, plus a bit of SRE type stuff. Without knowing the first thing about MEDDPICC, setting landmines for competitors, Command of the Message, or other sales tactics, I enjoyed immediate success. Knowing the technology domain eclipsed knowing how to sell (I had other tailwinds like fantastic account executives, a ridiculously good product, buyers flush with VC money, etc.).

The two sales engineers archetypes

Things have been going great! I’ve worked on some huge deals! Yay commission checks. But I recently started becoming concerned that having not worked as a software developer for over 3 years, I might begin to lose my advantage, and that is a direct threat to my viability as a sales engineer. I asked a director of sales engineering at a different company, a person with more years of this work under their belt than I have, to meet up and talk about it. He confirmed my assessment that there are two archetypes in this job:

The first is the technical expert. They win in engineer-led evaluations. They don’t need to be salesy. That’s me. The other relies on their sales chops. Theoretically, they are best deployed in more complex sales engagements where running an efficient sales process, delivering a lot of presentations, and consensus building across multiple departments. They can pull in the technical expert to assist as needed.

That second profile is so not what I strive to be. This seems like an incredibly boring workday. I like getting strategic on a deal with my AEs. I like improving my presentation skills, being smart about how I do discovery, etc. Those are good skills to have. I am motivated by marrying that with interesting technology projects.

In my view, these salesy SEs are really just veering into account executive territory. Being strategic in a deal is really not that complicated, and your account executive sucks (many do) if you think this is where you need provide value. In reality, I think most SEs who bill themselves as less technical but great at selling are just hoodwinking their leadership.

I’ve worked with SEs who have years of experience and simply got lazy about mastering their technology domain. I can cite a specific, large deal where they lost because they didn’t fully understand a custom, one-off solution provided to them by the RnD team, and it subsequently failed in POC due to misconfiguration. In other oppurtinities, prospects would ask tough questions like “how would I flip the frambulator through the tubulator?”, and the SE avoid the topic with the trick of asking “well how do you accomplish that today?” That question is a useful tool, but avoiding tough questions makes buyers think you and your product can’t solve their problem.

The honest path for the long-time SE whose technical skills diminish over time is to slide into progressively less demanding SE roles. I am thinking of one SE who interviewed for a job at Bitrise as an example. He was originally a developer. His start in sales engineering was with an application performance monitoring software company (selling to engineers). Ten years later, when I met him, he was selling a content management product (where the buyer is marketing, but there is some light integration work)–basically he found a product that was easier to master without deep engineering ability.

What do you do about it?

If you want to sell technical products to technical buyers, you must find a way to be seen as an engineering partner. As a self-taught developer, my instinct has been to find side projects, books to read, and online courses to retain and grow my skills. As I’ve gotten older, I’ve recognized that life makes this less realistic (for whatever reason - marriage, kids, energy levels, or just not wanting to give your whole life to the screen).

The technology industry also runs in waves–personal computing, the web, cloud, mobile, etc. My 10 years of mobile experience won’t earn me a lot of street cred if I want to get to into AI.

My conclusion is that a successful sales engineer has to be comfortable switching back and forth between the Camry and the four wheeler. A decades long sales engineering career is either overly salesy (i.e. just become an account executive if that’s what you want), or superficial in its enagement with technology. Personally I think there’s a chance that my next job will be as a software developer in whatever field interests me (web assembly???). Once I get the deep familiarity that comes from working on something professionally, every day, I can take that back into sales engineering. Whether I’ll want to or not is an open question.