The Tech Generalist Dilemma – Are You a New or a True Generalist?

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With MBA graduation upon us and a number of other folks I know looking to make career / industry transitions, I’ve had a few folks ask my thoughts on how to approach new jobs in the tech industry. Many of my friends come from a generalist background. What makes someone a generalist? Well, the simple answer is that you’re not a specialist. In technology, I think there are a lot of people who fall into the generalist category – if you don’t write code, aren’t a finance expert, or don’t do sales, you are probably in the generalist pool. Most generalists I know are interested in a mix of business development, product management, and marketing in their ideal job. They also want some “general management experience”, which I take to be a euphemism for figuring out how to work with others to get stuff done.

At the end of the day, I don’t think all generalists are created equal. In fact, I think there are two distinct types. I’ll outline the basics below:

“True” generalist – Someone who has both the experience base and the personality type that lends itself to wearing many hats. This type of person has done a stint in most of the major non-engineering functions in technology companies (marketing, business development, product management, and perhaps finance) and has some grasp for how all of these functions fit together. The “true” generalist has probably had the opportunity to go deep in one of these fields but prefers the joy of being able to wear many hats and seeks out situations where they can exercise that tendency.

“New” generalist – The “new” generalist is in a different boat. Most “new” generalists are generalists because they haven’t had the kinds of experiences that would enable them to present themselves as a “true” generalist. If you’re new to the world of technology and aren’t in danger of writing code, it’s likely that you’ll get steered towards entering the industry in business development, marketing, or product management (only under certain circumstances, though). The “new” generalist might not end up being a generalist for long – they might end up becoming a specialist in one of the generalist functions above or they might find that they prefer life as a generalist.

The reason this distinction matters to me is that my observation is that “new” and “true” generalists seem to be happy in very different kinds of companies.

Most “true” generalists I know tend to gravitate toward small (and I mean really small) companies – something on the order of 20 people or fewer. These are the kinds of environments where a true generalist can shine – there’s enough work to be done across all of the generalist functions to keep someone of this background and temperament engaged. However, as companies grow, most jobs get smaller and become more functional. That’s not a good thing for a generalist interested in breadth unless he/she is the generalist CEO.

I’ve talked to a handful of really successful “serial generalists” in the last few weeks and most of them seem to agree that what interests them most is being able to do a little bit of a lot of different things during the founding or embryonic stage of a company. Most also admit that they’re not the best at any one specific thing, but they are great utility folks. Also, they’re not the same as the “inexperienced but can figure out how to get stuff done quickly and efficiently” crowd – that’s the domain of the new generalist. Most true generalists I’ve spoken to seem to have a pretty clear sense as to what they’re good at doing and why – many of them are also the non-technical co-founder in most of the ventures in which they get involved.

Life is a lot different for the “new generalist” in my view. I think the new generalist has a much more challenging task.

-0 to 20 employees – This is a tough place for a new generalist unless you really know the folks with whom you’re working. Companies of this size generally tend to look for folks who have “done it before” as generalists and can wear many hats.

-20 to 50 employees – At somewhere around 20-30 employees, specialization often starts to set in. In lieu of generalists, it’s often the case that companies add experienced folks who can carry the water already. For example, your first marketing hire at 20-30 people is more likely to be someone who’s done marketing before and can grow with the company than it is someone who can learn on the job. This is no accident – if you’ve reached this size you probably have raised some venture capital and have a plan that calls for becoming a much more substantive entity in short order.

-50 to 200 employees – I’m at a loss here. I’ve seen new generalists find great homes at companies of this size and I’ve seen it end terribly. This is an awkward size for any company. You’re too big to be small and too small to be big. Often times I’ve seen companies that can digest a small number of new generalists at this size, provided that they’re not concentrated in any one function / department and that you have strong leadership at the top.

-200 to 1,000 employees – I happen to think this is a great place for the “new generalist” to join. There’s enough management structure and momentum in place that a new person will have mentors from whom he / she can learn. Also, jobs are usually big enough to be meaningful and interesting to a new person. As the company grows, the new generalist can grow with them.

-1,000+ employees – Big companies are hard for “new generalists” to crack. By the time you get to this size, jobs tend to get more functional and it’s harder to operate in generalist fashion. The only real way a generalist can really grow in this kind of environment is by functional rotation – doing short stints within a company in a number of different functional roles.

This is my first blog post in a long time so I hope it’s coherent. I also know a lot of you have thoughts on these topics, so feel free to comment below.