I originally had this on the blog section of my website, but moved it here as I didn’t feel like the quality of writing was high enough.
learn from my mistakes
I decided to leave BCG in order to move closer to my girlfriend in the San Francisco Bay Area, and since I was moving to Silicon Valley I thought I’d try to enter the field of Product Management (PM). BCG is insanely generous in giving folks that leave on good terms time to remain legally employed as they job hunt (the so-called “transition period”) - my plan was to use that time taking the GMAT (month 1), traveling a bit (months 1 and 2), and then prepping for interviews (month 3) and recruiting (month 4).
Hindsight is 20-20, but in retrospect this was insanely naïve – I planned to only spend one month (out of four available) on recruiting, but it took longer than that to land my next role which (1) created an employment gap and (2) tanked my leverage in negotiating my next role. An employment gap isn’t the end of the world, but it can certainly create unnecessary stress in your life (in my case – both from my parents giving me shit and from my own self-created stress). Furthermore, more transition runway allows you to walk away from suboptimal offers and continue the search for something you want more. Consider these scenarios: you’re 3 months post-transition and you get a C-tier job offer vs. you have 3 months left in transition and you get a C-tier job offer. Rule number one of negotiations is that your power is defined by your BATNA (Best Alternative To a Negotiated Agreement), in this case your next best job offer (including those you don’t have yet). The longer you’ve been unemployed, the more desperate you’ll be and the more you might consider taking a job you may be soft-committed to for the next year.
My intent with writing this is to walk you through what I wish I had heard (and done) the day before I went on transition.
WHAT ARE YOU LOOKING FOR?
I like to think about jobs as having 9 dimensions on which you can rate them — in no particular order, they’re (1) salary and benefits, (2) work-life balance, (3) location, (4) who you work with (people and culture), (5) learning and growth, (6) what you work on, (7) compatibility with future goals, (8) prestige, (9) social impact. It’s important to figure out what your objective function looks like – What’s critically important, and what’s flexible? What are the dimensions you want to optimize vs. the dimensions you’re just shooting for “good enough”? What does bad, okay, good, and great look like for each of those dimensions? Maybe you don’t care about earning more than $150k and would rather optimize for the best team you can find, or maybe you just want to make sure the vibes aren’t off while you seek the highest total compensation you can find.
As another example, here was my personal objective function:
Must-haves: Location (in the SF Bay Area), Salary ($125K+ Total Compensation, or TC), >30 and <60 hours/week, sets me up for B-school in 2-5 years if I choose to go down that path
Should haves: Salary ($150K+ TC), ~45-50 hours/week, good vibes from the team, PM / Business Operations / Strategy / Chief of Staff / Program Manager / other product-adjacent role title and responsibilities
Nice-to-haves: Salary ($200K+ TC), organizational prestige, social impact through the job itself, some travel (~25% of weeks), extra bonus points for being a PM
Understand the job market for what you’re trying to do
My main mistake was not understanding what the job market looked like for PMs. In short – terrible. Awful. I wasn’t going to be a PM no matter how hard I tried. Chime (perhaps you’ve heard of them, but perhaps not) got 1,200 applications in 48 hours for a PM opening. Microsoft is asking for X years of experience if you have a PhD, X+Y years of experience if you don’t, and getting people with PhDs and X+Y+Z years of experience applying to their roles. Had I figured this out before I spent a month prepping for PM interviews, I could have been in the interview pipeline for several companies a whole month earlier (and doubled the amount of time I gave myself to find a job).
Perhaps interview prepping before applying to roles was the problem, but I believe it depends on (1) your ability to interview and (2) how many shots you can fire. If you’re looking to go into a field where there’s only a handful of players, then you need to make your shots count. Likewise, if you’re so bad at interviewing that you’ll just be wasting your time by applying to roles, then you should spend the time on prepping for interviews first.
Once you pull the trigger…
This is a marathon, not a sprint. Pearly whites are not going to be achieved by brushing your teeth nonstop for 24 hours before you go to the dentist; finding a job is going to require daily searching, follow-ups, reach-outs, and (eventually) interviews until you sign on the dotted line. Interviewing is a skill that you’ll improve on naturally over time (though feedback is hard to come by). Finally, getting a sense of an A-tier job vs. a B-tier or C-tier job takes understanding what’s out there in the market – companies post new jobs on a daily basis; a point-in-time snapshot isn’t going to necessarily give you the context you need. For me, job hunting was a 5-day-a-week, 2-to-4-hour-a-day commitment.
In terms of searching, I found luck through reach outs on LinkedIn from recruiters and company job boards. Setting my LinkedIn location to the Bay Area and changing my headline to “Seeking biz ops, strategy roles in the Bay Area” did wonders for the number of recruiter reach outs I got. Tracking my submitted applications was useful for gauging where I was getting traction, and a bit of color coding was nice to highlight where I needed to follow-up with folks. I found it helpful to track (in a spreadsheet) a list of company job boards (i.e., careers pages for various companies) and the date I last checked them. If you need help thinking about which companies to include, LinkedIn is helpful for generating ideas, though apparently some of the jobs on LinkedIn are fake (not sure what that means, exactly – just avoid concerns by applying directly through company job boards). You’ll want to revisit company websites several times (if your search extends that long). Here’s a template you can use.
Employee referral are nice-to-haves before applying. At a minimum, talking to someone to understand the company culture is no-regrets; at best the referral can heavily influence your ability to get a first-round interview. That said, don’t wait too long on a referral – my rule of thumb is to apply with or without a referral within a week of finding a job, since older job postings are more likely to have candidates in the pipeline already (thereby lowering your odds of landing an interview), and I personally focused on job postings that were under a month old.
In any case, it’s important to have a “backup plan” – a sense of when and how you’ll allow yourself to start compromising on your job search. I spent about 2 weeks of searching for PM roles before I began applying to product-adjacent roles that would set me up to make a lateral move into PM later. As it turns out, I went from zero traction to actually landing interviews with Business Operations / Corporate Strategy roles.
Final words of wisdom?
Here are some links to things I’ve written about in the past which you may find helpful (or at least interesting):