How I transitioned from Recruiter to Product Manager

Annie Li
How to ACELR8
Published in
5 min readMar 9, 2022

The job title “Product Manager” never really crossed my mind when I pictured my future career. Product Managers have always seemed like these mysterious creatures that work between engineers and designers and other parts of the organization, and no one can really pin down what they do. Yet tech companies somehow can’t live without them.

A cartoon bear tapping a laptop keyboard repeatedly.
A product manager at work (probably).

Using my job to help the other side

In 2020 when the pandemic hit, I, a recruiter with not so many years of experience (1 to be exact) started getting a lot of messages asking for job search help. As so many people’s lives were impacted by the layoffs, I wanted to help them as much as I could. I opened up my Calendly link to anyone on the internet so they could book a 30 mins call with me for free job search advice.

A LinkedIn post by Annie offering free job search coaching with a Calendly link.
The LinkedIn post that started it all.

In the following month, I had almost one call with a jobseeker every single day. It turns out everyone faced the exact same challenge — everyone applied to way too many LinkedIn job ads and with little to no success (here’s why it doesn’t work). And I only realized a few weeks ago that what I did was essentially user research, an important part of product work.

Forward and honest career conversations

Working in the field of recruitment and HR, we always have a finger on the pulse of people trends in the startup business, and that includes countless horror stories of how startups can fail their employees. Needless to say the pandemic revealed even further their reluctance towards change. I heard stories of rampant sexism, racism, abuse, lying, belittlement, gaslighting, you name it. Many talented people were extremely hurt or burnt out and even forced out of jobs they used to love.

It shouldn’t have to be that way. These stories made me furious, and I thought to myself: if these are the companies that end up raising millions, then I can do it too, and do it much better.

I wanted to found my own startup.

Luckily, my CEO is a very down-to-earth and easygoing boss, and my manager was a very empathetic and supportive person too. They created a very open and safe space for me to be open in our 1-on-1 conversations. Don’t remember when exactly but I started telling them, “A few years into the future, I want to found my own startup.” Pretty sure I said this again and again and again in every single subsequent 1-on-1s whenever I was asked about my career plans.

A trigger for action

In the meantime, I kept myself busy on the side. I built my own website to offer more focused and structured job search coaching on a weekly basis. I spoke at three different online career events in the course of a few months. I started writing the first edition of my newsletter. Whenever I had a chat with my CEO, I’d casually bring up these activities.

One day in August 2020, I finished a free coaching call with someone that booked me via my public Calendly. A few hours later I glanced at my phone and saw a Paypal notification: “You received €15 from [Person I just coached].”

People actually thought my advice was valuable! My efforts meant something! €15 was not a big amount but I was over the moon. I posted a screenshot on social media and my CEO reacted to it.

A few days later, my CEO brought this up in our conversation. “Really cool to see what you’re doing with coaching.” He said. “You know, we’ve been thinking about building our own product in the company and I’d like you to be involved.”

Four people sitting around a table in an office space having a discussion.
Our first product workshop, summer 2021.

Changing paths within the same company is the easiest

A year and a bit later, my job title is now Product Manager. Of course, the change was not overnight. At first I was asked to try and give feedback to our MVP. Then a few months later I negotiated for an informal quarter-time (10 hours per week) role working on the product. In January 2022, I finally signed a new full-time contract as Product Manager.

And trust me, the new role was extremely difficult at the start. I had no Head of Product above me telling me what to do. I had no in-house engineering or design teams. My schedule went from an extremely structured calendar with interviews and hiring manager meetings to a blank canvas that my busy recruiter brain was very uncomfortable with.

I also had no idea how to be a product manager at all and had to carve my own path. I found 10 product articles to read every day, started Udemy courses, spoke to 4 mentors, watched YouTube videos, read tons of Tweets from Lenny Rachitsky and Shreyas Doshi. I’ve dreaded going to work many times and even cried after video meetings. But 3 months later the hard work did pay off. I no longer feel flustered and know what’s coming up every single week for our product.

For those of you reading and are thinking about a career shift from one discipline to another, consider shifting within your current company before looking for a new job. I’ve coached 100+ jobseekers and seen the competition from the recruiter side, and job searching is very difficult — especially for career changers. Most bootcamp graduates do not land their ideal jobs within 3 months (source: my partner went through a bootcamp, my friend worked at another bootcamp, I coached 5+ bootcamp grads).

Here’s what you can use as a plan instead:

  • Think very, very clearly about what you really want to do. I didn’t do this enough, but speak to people who work in your ideal job to understand what that job actually looks like beyond buzzwords.
  • Put out some feelers in your current company. If they have an open attitude towards their employees’ careers, share with them your plan. It doesn’t have to be detailed, simply “I’m interested in X and want to pursue X in 3–5 years”.
  • Your company doesn’t have to have this role yet. ACELR8 didn’t even have anything closely related to product, but it was forming at the back of the strategy.

Filling a position from an internal move is also hugely beneficial for the company: someone like you already know the company inside out, built solid work relationships with important stakeholders, and it saves lots of money and time that would have otherwise been spent on hiring from outside.

I’m not the only one who made a change within ACELR8. My colleague Aidos went from a client-side Talent Partner to being our inhouse Recruiter, Angela became our first Talent Manager building learning and development programs, and Ludo moved to sales and became our first Business Development Lead.

If we can do it, you can do it too! Your dream job could be much closer than you think.

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Annie Li
How to ACELR8

Startup recruiter, job search coach, public speaker. Breaking the wall between companies & job seekers.