Advice for generalists who want to join startups
How to get hired as a generalist at a fast-growing company
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Most early-stage startups are focused on two things: building stuff and selling stuff. So where does someone with a more “generalist” background fit in?
We receive many emails from many current and former consultants, investors, and students about this topic.
Their questions tend to look something like this:
“Hi, my name is [Redacted]. My background is in finance, where I spent 2 years in Investment Banking and 2 years in Private Equity.
I’m looking to transition into tech and join a growing startup in a business operations or chief of staff or more generalist role. I’m the type of person who is open to doing any sort of role, really whatever it takes to add value.
I had a few questions that I would love your thoughts on:
How do you recommend positioning myself to employers?
What can I do to increase my odds of getting hired?
What is the specific type of role do you think I should go after?
What are the types of companies that you think I may be a good fit for?
Is there anything I should do now before joining a startup that would set me up for success?
Would love your thoughts!”
In the rest of this essay, we’ll attempt to answer these questions to the best of our abilities. Hopefully it’s helpful! If you have any more questions, feel free to send us an email: hi@nextplay.so.
How should you get a job as a generalist?
You may be looking for a concise phrase to summarize your skillset. Because when people ask you what you’re good at—be it during an interview or even while at dinner with your friends—what do you, the “generalist”, have to say?
People who code software call themselves software engineers. People who sell software call themselves salespeople. But what does someone who…is a “good problem solver, a strategic thinker, a creative hustler”…call themselves?
My quick answer for you: I do not think it really matters. I would stop wasting time thinking too much about the optics.
You can spend many many hours trying to come up with the perfect terminology. You may even convince yourself this’ll be the difference maker for your job search. I do not disagree that you could (and in certain circumstances maybe should) go about optimizing your resume and coming up with a creative bio for your Linkedin.
But, in talking about startups especially, I have rarely found these details to make much of a difference.
Instead, I have another approach that I think will lead you to materially better outcomes. I think it’s better as defined by: it’s more likely to help you get a job that really aligns with what you want (in a reasonable amount of time).
The approach is this: you should find a way to show, not just tell.
What does it mean to show not tell?
This whole “show not tell approach” will sound rather obvious but believe me when I tell you it’ll make a really big difference.
Here’s why: The default approach most candidates take when applying for a job is to simply apply in the portal and let their resume do the talking. The slightly more ambitious and effective version of this is sending a cold e-mail to the founder or hiring manager (ideally a good one!), letting them know you’re interested in joining their startup.
Where “show not tell” comes into play is in the contents of the outreach. Many people with a more generalist background reach out with a message that says something quite general about their interest. Like in the example I gave above, I commonly see people say something about “taking on any responsibilities” at the company.
While on the surface this sounds like it could be a great idea—being the type of person who will do “whatever it takes”—I find it’s actually not the most effective introductory framing.
Why?
Well there’s a big difference between hiring someone who needs to be told what to do and hiring someone who can figure out how to be valuable on their own.
If you put yourselves in the shoes of the founder or hiring manager, time is actually your scarcest resource. Because of this, there’s actually a big cost to onboarding a new teammate. That time spent is not always worthwhile. Especially when you take into account opportunity cost, many new employees actually contribute negative value, particularly in their first few months of the new job.
If you are hiring a software engineer, fine, it’s generally quite straightforward to figure out what sorts of projects they’ll be able to productively contribute to.
But if you are hiring someone with a more generalist skillset, it may be a lot less clear where they’re likely to really drive a lot of value. It is not obvious what context they need to be successful and where they are most likely to succeed.
And so I think my number one piece of advice is to find a way to prove that you can identify (and even do some!) useful work before you are even hired by the company. That’ll make you a candidate who really stands out and increase your odds of getting hired.
As mentioned, very few candidates take this part very seriously. They spray and pray as opposed to really honing in on a compelling reason for companies to hire them. I think that if you simply take this idea seriously, and actually apply it to let’s say five to ten fast-growing companies, you’ll be genuinely shocked by the results you’ll see.
Regardless of if you end up getting the job, it’s also a step in the process you can take that’ll help you answer a few questions for yourself like what type of work do you like doing and do you find the work at this company interesting? You don’t have to wait until you are actually working at the company to answer these types of questions. You can start now, before you are hired.
So how do you actually go about doing this whole “show not tell” approach?
Here are a few examples you can take as inspiration. But please note, we would highly suggest thinking for yourself to come up with the best answers for you and your situation.
Let’s imagine you wanted to try to land a job at Meter. Meter is a Sequoia backed internet infrastructure startup that somewhat recently raised a $170m Series C. They are hiring for 60 roles right now in SF and all over the world.
How can you as a generalist increase your odds of success when applying to the company? How can you apply this “show not tell” mentality to the application process?
Well it looks like (just looking at their careers page) they are hiring for many operations and project management roles. Those could be interesting to someone with a background in consulting or banking. But also, there may just be more opportunities that they are not currently listing on their website.
So here are some ideas (note that we did not write this post in collaboration with Meter and none of this is actually guaranteed to work—they are just our ideas :)):
It looks like they are hiring a technical evangelist, someone to promote their product within the IT and networking community. That probably means they are looking to grow a community of sorts. I would read Reddit threads, join Slack groups, and even talk to existing community leaders in the IT community. I would summarize my learnings in a google document, and highlight what I see as unique opportunities for Meter to build a brand of their own.
I would see that Meter is hiring for 60+ roles! I would imagine that one of the top priorities for the founder right now is hiring great people. I would look up the founder, Anil Varanasi, and email him creative answers as to how he could accelerate the hiring process. One example is I would send him a cold email offering to document their existing hiring process end to end for him, identify bottlenecks, and proposed solutions. I would come up with many more examples and even find sample candidates and describe you’re approach you’d take to quickly getting in front of them.
I would go on Linkedin and look at their employee team page. I would find one of their non-founder early employees, because I imagine this person would be influential at the company if they were still there. In this case, I would find Liam Weld, who looks to be a generalist who has taken on many roles at the company and is now working on “data centers.” I would then spend 30 minutes researching data centers + internet infrastructure, and compile my learnings in a report I send via cold email to Liam. In that report, I’d offer specific things I could do that would help Meter grow in that domain.
Let’s do another example. This time, let’s try for a much smaller company.
Alex Dees is the founder of Meridian. They are building a platform that helps companies track how they appear in AI search. They launched two months ago via a fairly viral Linkedin post that resulted in hundreds of new customers. They are still a small team (<10 people) and hiring for 6 roles.
How would I get a job at Meridian? (Again we did not write this post in collaboration with Meridian and none of this actually guaranteed to work—they are just our ideas :)):
The company recently launched. I would imagine the product and user experience is still very much a work in progress. Sign up for the product and document the user journey as you go, including any emails you receive from the company. Turn it into a presentation with all of the things you would do to improve the effectiveness of the funnel and email it to the founder.
Look at their customer page and find 10 potential customers who seem to be in their target profile. Two options from here: 1) write a strategy for getting in front of those customers and send it to Alex or 2) actually reach out to the potential customers and interview them. Ask them what they’d think of a product like this and share their insights with Alex.
Put yourselves in the shoes of a prospective customer. What questions do you have about a product like this? Write out those questions and then suggest a content marketing roadmap that’ll really resonate with the audience.
I would notice that Alex is posting often on Linkedin. I would wonder if he’s maximizing the efficiency of each post. Is he following up with every person who engages with the content? I would find a way to scrape the comments of some of his more popular posts and organize the responses in a Google Sheet. I would categorize the responders by persona and suggest a strategy for getting in touch with each person (perhaps that means setting up a drip campaign or a targeted email).
I hope you are starting to get the point. And to make it really clear, the point is this: if you are actually a generalist, if you are actually someone who can “plug in anywhere” and exercise your strategic thinking skills, then do it! Show, not tell.
If you’re looking for a more specific role like sales or engineering, you can also use this approach. It just works particularly well for generalists who want to join startups because it quickly helps you substantiate your rather abstract-sounding skillset.
Next up, you should try it out! Seriously. Let this essay be your excuse for getting started. There are loads of really interesting opportunities on Next Play. Take three of them and see what you can come up with.
Depending on how badly you want or need a job, I would not spend more than thirty minutes to an hour per company. If you find this process slow or you’re struggling to do it, send us an email: hi@nextplay.so, we would love to find a way to be helpful.
(You may also like Friends of Next Play. When you join you get invited to our Slack where you’ll meet loads of like-minded people)
This is very good advice , I joined my current nuclear startup because I cold emailed the ceo , did a similar thing and offered to do an internship to find my exact niche . It helped me pivot from SaaS founder to hardware R&D
This is a very useful article, and a great read.
I strongly agree that for generalists it’s incredibly difficult to achieve coherent positioning through terminology alone — whether on LinkedIn, in a resume, or in personal communication — simply because the language available to us is built for a world of specialization.
Speaking from outside the startup bubble (many years in nonprofits and cultural marketing), I’d say that the approaches you describe may sound naive at first, but are actually very effective. As a small real-world example: we recently hired a project coordinator who was a young generalist and who did almost exactly what you’re describing. Not fully, not perfectly, but the attempt itself made a difference.