I was frustrated. Beyond frustrated. Product management was my dream job; but no matter what I tried or how hard I tried, I could not break in. I just couldn’t get my foot in the door and land that first job.
Over the years, I tried landing that first job on several occasions, each sustained attempt ending in total rejection. I went to a good college and made good grades; but as a philosophy and business double major, I lacked the technical degree tech companies wanted on a resume.
So, I went into management consulting. Next, I tried enterprise software sales. Then sales operations. Then program management. By this point, I had worked in a tech company for years in various roles. But even with the network of people I built (including product managers and executives), I was no closer to landing a job in product management than before.
Before every career change, I applied to jobs in product management. Each time I applied to product management, several years had passed and; over those years, I gained more professional experience, a bigger network, more skills and further established a track record of success.
I did all the right things: followed all the best advice from blogs, mentors and people in tech and in product. I read up on the product skill sets. I went to networking events. I connected with product managers at my company as well as at other companies. I asked highly placed people in my network to refer me for product management roles. I even managed to get a meeting with the CEO of a large tech company I worked for to pick his brain about product management. He had worked his way up to the top job through product management.
I applied to giants such as Google, Apple and Microsoft down to small startups with only angel investors and everything in between. I researched each company before applying and carefully crafted a thoughtful cover letter explaining why I would be a great candidate for the role. I spent hours on some of those applications, making sure everything was perfect.
Everyone from consultants to product managers to CEOs of billion-dollar companies reviewed my resume a dozen times over. Despite all that, I was lucky to get even an automated rejection email.
At a few companies where I had strong network connections who referred me, my connections ferreted out the cause of rejection from the recruiter. It was the same every time: not enough product management experience. Incredibly, this included entry-level product management jobs or “associate product manager” positions, as they are frequently called.
So, there I was—smart, successful, hardworking and completely incapable of breaking into product management. I knew I could do the job. From talking with product managers, observing their work, and getting pulled into small projects with engineers and designers, I knew I already had many of the core skills successful product managers needed to have.
I reviewed my options. Product managers seemed to come mostly from engineering or design. I could try to retool for one of those professions. Not having a degree in computer science also seemed to be a deal breaker for those who might otherwise take a chance on me, despite the general insistence from product manages that a technical background was not a prerequisite.
I could go back to school. A master’s in engineering or an MBA (Master’s in Business Administration) both seemed like strong enough credentials to get me through the door. But those options ranged from one to two years of time commitment and $50,00 to $150,000 in tuition cost, depending on the school and program, not including the opportunity cost of forgone wages if I went to school full time.
Bootcamps were another option. They became popular in the tech world over the last few years (mostly teaching coding), and a few had product management tracks. I personally knew people who learned to code and landed a great job as a software engineer because of a bootcamp. But I also knew people who invested the three to six months and $3,000 to $10,000 in a bootcamp, only to gain some skills and a certificate and hit the same impenetrable barrier as before and failed to land a job, despite the employment stats and career services the bootcamps touted. Like colleges and universities, bootcamps’ business was selling people on their courses, and they only needed enough successful outcomes to advertise.
As unpalatable as going back to school or signing up for a bootcamp was, I was out of options. I needed to make a gamble or give up on product management because, clearly, the methods I employed didn’t work.
I was working as program manager at the time, and a number of companies recruited me for senior program manager roles. I didn’t love the job, but they offered a lot of money. And it seemed like product management was an unreachable a goal. I resolved that if I didn’t make any meaningful progress towards a job in product management by the time the company made me an offer for the program manager role, I would take the offer and give up on product management.
Two days after I made that decision, I stumbled across an advertisement for a workshop promising to teach people how to land their first job in product management. It cost $15 to attend the event; and while I wasn’t hopeful that I would learn anything new, I figured, “Why not – what did I have to lose?”
To my surprise, the workshop did not just repeat all the “best practices” for getting into product management that had failed me so many times before. Even more, the core thesis of the workshop resonated with me. It framed interviewing as an imperfect system where recruiters and hiring managers fall back on filters and biases (like job titles and prior product experience) in the absence of real means to evaluate a candidate’s skills. To me, this explained how I could be a great product manager yet never get a return email acknowledging my application. The answer, the workshop said, was to focus on interviewing.
I attended the workshop and left thinking about the application process in a new way. Slowly, and with a lot of trial and error, I changed how I applied for product management jobs. And then, unbelievably, I started getting interviews.
At first, I didn’t get far in the interviews, but I took a new approach to interviewing just as I had with applications. I continued getting interviews with new companies, and I began getting further in each interview process – and within months, to the final round of interviews – even getting flown to an onsite interview.
And then I got my first offer, with several other interviews at their final stages. That gave me the confidence to keep interviewing until I found a product management job that paid well, was with the right company and fit what I looked for. That was an amazingly long way to come from begging for scraps and being willing to take any job as long as it was in product.
Four months after I adopted this new approach to job hunting, I signed an offer for a mid-level product management position at a company I was excited about, with competitive compensation.
It still amazes me that all it took was a new approach to accomplish in a few months what I previously failed to achieve in years.
Product management turned out to be everything I hoped for in a career and is a natural fit for my skills and interests.
I decided to write this book for others in the position I was in – a great fit for a job you just can’t seem to land, no matter how hard you work. Whether you come from a role close to product or from a role and industry completely unrelated, I want to share with you the perspective and methodology that I found transformative in my journey to product management.