HOw I recruited
know thyself
The best thing I did during my last recruiting cycle was write a short document on what I wanted: my long-term goals, what drove my day-to-day happiness, what I had done previously that I did / didn’t enjoy, what I thought I might enjoy. I’ve included an example here.
Using AI to help me recruit
Claude can be an excellent helper during your job search. Broadly, the approach I found helpful was:
Write out a document outlining what you’re looking for (see above)
Build a list of companies that you’d be interested in. Use Claude both to add to that list and to subtract from the list: you might ask e.g., “What are some companies that I don’t have on this list that I might consider?” or “Read through the companies on this list, and give each one a score from 0-10 based on their trajectory over the next couple of years”. You can turn this into a Skill and re-run it on a monthly basis.
Have Claude scan every job board from the companies on the list, and identify job postings that you’re a good fit for (you’ll probably want to give Claude with your resume or LinkedIn). Have it output a list of roles for you to consider with 0-10 scores representing how good of a fit it thinks the role is. You’ll probably want to give feedback to Claude on where it was too optimistic / too pessimistic / where it nailed the recommendation. You can turn this into a Skill and re-run it on a ~weekly basis.
Apply to roles as you see fit. Automating the application itself doesn’t feel like the right call - I think the better move is to try and get a personal referral / intro at any company you’re interested in. It’s more effort (and therefore requires you to be more intentional about which opportunities you prioritize), but I think it leads to a much higher hit rate.
Here’s a folder with the whole system (you can point your Claude to the AGENTS.md file and it should be able to build the whole thing for you). As a caveat, while I was doing this, I was on a $200/month plan so that I wouldn’t get rate-limited or be forced into using a worse model.
So, you want to work at a startup
If working at a startup sounds like what you’re most interested in, I have a few thoughts:
Location
You should expect that you’re most likely going to live in San Francisco. That’s not to say that there aren’t other cities with startups (e.g., New York), but the concentration of high-growth startups is undoubtedly in Silicon Valley. I remember hearing all about the California transplants moving to Austin and the tech companies relocating there back at the beginning of COVID. After my stint at a VC firm, I can tell you that the S-tier and A-tier startup companies are by and large in Silicon Valley, and there doesn’t seem to be any sign of geographic dispersion. Perhaps this might change if you were interested in a startup tied to a very specific industry (e.g., fintech startups may have more presence in NYC), but you’ll probably end up in the Bay Area.
Building the top of your application funnel
The fastest and easiest way to compile a set of companies that are strong is to index to which companies are taking checks from S-tier and A-tier VCs. This is not a guarantee of success by any means, but the whole point of a VC firm is to identify the fastest growing startup companies and get into them early. VC firms don’t always get it right; the vast majority of early-stage investments go to zero! But at a minimum, “Sequoia Capital led the round” is a positive sign that smart people think that there’s something behind the team and the company that’s worth betting on. You can (and should!) invest your time and effort and energy to know a company later on, but I’d recommend using “top-tier VC-backed companies” as a good shortcut to identifying the companies worth focusing on.
Timing
I really like Dan Hock’s piece on When to Join a Startup. However, I distinctly disagree with his point on after a funding round being a bad time to join:
It’s common for candidates to flock to a startup that recently got a big new funding round and big new valuation. This is exactly the kind of thing to avoid, because the upside was just built into the value of your equity grant.
More important than optimizing the exact time you join a company is picking the right company in the first place. The people who joined Anthropic are surely happier than the people who joined some random company that ultimately went bust, but joined just prior to the company’s next funding round. From a financial perspective, most startup equity has a binary outcome; you should try to be on the right side of the binary! I’ve also influenced by the notion from investing that you shouldn’t try to beat the market - here, funding announcements are signals from the market on what’s working. Figure out what stage of company you want to work at, then build your top of funnel accordingly.
That said, I do agree with Dan’s point on not being one of the first few (single-digit) employees. The equity that you can receive for being Employee #1-9 isn’t meaningfully higher than the equity you’d receive for being Employee #10-99, but you’re taking far more risk. Put another way, if 90% of companies that raise a Series A die, then unless you’re getting an equity grant that’s 10x the size of the employees that join after Series B, you’re making a negative EV move.