Episode 49: Generalist or Specialist - what's better for your career?

Early in your career you don’t have a lot of skill sets, so best advice is try things until you find one you particularly enjoy and then spend the time repeating/learning how to do it better.

It may take a few rounds of experimentation (switching industries or roles or stage of company) until you find the function you want to own. Then you should think of yourself as a service provider. You can sell your service to companies and should be paid in exchange. They may do that by hiring you full-time, contractor, or something in between.

Either way - the better you are able to deliver the more you should get paid. If you aren’t being valued (i.e. your compensation doesn’t reflect the value you deliver), then you simply take your services elsewhere.

Note: Above advice assumes it’s time to leave your company — I wrote about the signs here. Above also assumes promotion isn’t possible — if it is, reference how to bring up promotion + promotion prep.  

At a certain maturity, you will hit a wall where you need to decide — should you become a specialist (double down on one aspect of your job) or generalist (continue finding new/better ways to do all aspects of your job)?

It’s a question I’ve been debating for the last 6 months. The doors within my job have opened because of a specialty gap. However, there have been interesting consulting opportunities that require a more generalist approach. My specialty is helpful but not the only requirement.

My perspective on this has been changing over the last 12 or so months, so sharing what’s informing my latest perspective:

Stage of company

Pro for specialist:

My world view working in tech (particularly early stage to high growth startups) is the life-changing money gets unlocked when you can scale with the company. Join early and stay until exit.

My specialty is in pricing (both from the product side of what should be free vs. paid and the sales side of explaining and defending the pricing). The larger a company is, the more complex and nuanced its products become, which makes things like pricing a harder job and, therefore, requires a dedicated human who has done it before to figure it out.

Hard job = higher willingness to pay (if you can truly solve the problem) = job security + get paid.

Con for specialist

At earlier stages of companies, pricing is still a major lever for the business, but with a single product and a single buyer, it is difficult to separate pricing out as a standalone function. It needs to be tied to something more general - e.g. manage the roadmap, decide on features that are valuable, price & position them all in one role.

Pricing as a specialty though is a clearly defined scope that makes perfect sense for a contractor/advisor to do part-time and have internal full-time folks focus on all the tangential parts of pricing (tying back to roadmap/selling to customers).

Takeaway(s)

1. If the goal is full-time role at early-stage company —> generalist is the choice with more options

2. If the goal is contract (at early or late stage company) —> specialist is the choice with more options

Reinvention

My career journey has been primarily in marketing - specifically product marketing. Here’s a quick overview:

• Marketing: sales development (1 year)

  • responsibilities included: positioning, competitive & market research, and unparalleled willpower

• Product: product marketing (1 year)

  • responsibilities included: product launches (pricing & positioning), sales enablement, and competitive intel for one specific product

• Marketing: product marketing (2 years)

  • responsibilities included: product launches (pricing & positioning), sales enablement, and competitive intel for one specific product

• Marketing: competitive (2 years)

  • responsibilities included: competitive enablement & win/loss program across all products and competitors

• Finance: competitive & pricing (1.5 years)

  • responsibilities included: product launches (pricing & positioning), competitive research & enablement, and win/loss program across all products & competitors

I’ve (unintentionally) become a more and more specialized function of marketing. I’ve also reported to different functions, worked in different industries in every role, and started/scaled functions at multiple company maturities.

When I first went down the path of competitive, I was concerned it would be a one-way door — once I branded myself as a “competitive guy” I would never be able to go back to product marketing or do anything else.

The reality is competitive often sits within the product marketing team and there is always more work than people, so picking up product launches or other product marketing projects was always an option.

Similarly, in finance (rare to see competitive there, but competitive + pricing makes so much sense), I have had to reinvent the scope of focus for the team, which has also allowed me to broaden the types of impact I have. It’s pushed me to further refine the service I offer.

Takeaway(s):

1. Honing in a specialty is a two-way door —> you can always go back to what you were doing before if you’d like

2. Going from generalist to specialist forces you to reinvent yourself which makes you a better generalist in addition to specialist

Part-time vs. Full-time

In the ZIRP (‘20-’22) era where capital was abundant, companies were hiring left and right. When I was searching for a role in Dec. 2019, I had 10 interviews and 4 offers in 7-weeks. It was insane.

Previous to that I had always thought about the gig economy — instead of one job that pays me $100k+, perhaps I should look for multiple gigs that could pay me $20-30k. They would be of varying difficulty but then my risk is also diversified as I’m not dependent on any one thing.

I looked into AirBnB, Turo, reselling on Amazon, paid surveys, and a host of other things like buying car washes or laundromats. In the end, I thought honing my services in tech would be worth the payoff in the long-run and that I could just become a consultant part-time after 1-2 IPOs.

Fast-forward to 2025, it’s clear that IPOs — the ones that come with life-changing money — are extremely rare so those side gigs would have to come into play much earlier than I thought.

So then I refocused my career on building a skillset in my main gig that I could easily monetize (widely needed / hard to do) which is how I happened to land on Pricing. Note: I actually really enjoy it - but knowing it had high utility made me even more excited to learn.

As an experiment, I’ve been pitching companies at different stages to bring me on in an advisory capacity. I offered concrete buckets of work like pricing consulting (specialist), product launch help (generalist), and competitive research & enablement (specialist).

Consistently, I find more opportunities for product launch help but a lower willingness to pay. While there are fewer (or at least I have found it harder to find viable opportunities) for pricing consulting, the willingness to pay has consistently been 2x more than product launch help.

The bucket of competitive research & enablement is almost table stakes (I get asked to add that into product / pricing consulting), which as a buyer I agree with. If you’re doing product/pricing work effectively it has to be informed by the market landscape.

If my goal is to do side gigs in addition to my main gig, then pricing is the obvious choice. I get paid 2x with ½ the clients - win/win. I’ve asked many founders why the willingness to pay has been so much higher on the pricing side and the tldr is it’s clearly understood the value pricing can bring when you get it right, but it’s very unclear on how to actually do it (or too easy to get it wrong).

Takeaway(s)

1. The specialiest generally has more value, but only if it’s something generally applicable enough (e.g. every company has a pricing lever they need to pull) and not many people know how to do it well enough / it’s hard to learn quickly without real experience.

As always, feedback is a gift and I welcome any/all feedback on this episode. See ya next week!

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