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How ACTUAL Job Seekers Have Succeeded in this Market
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Getting a PM Job

How ACTUAL Job Seekers Have Succeeded in this Market

I've connected with 5 job seekers who successfully get jobs in this tough market. Here are the key lessons from their stories.

Aakash Gupta
Apr 02, 2025
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One of the things is no short supply these days is advice. But what is in short supply is actual case studies.

So that’s what today’s post is: stories of successful job seekers - not theory on what works.


The Market Is As Bad As Ever

Every 3 months, we check in on the job market in this newsletter. And the news is in: Q1 2025 was a return to the lows we saw in 2023.

2025 layoffs in Q1 had already exceeded the totals in 2023 and 2024 by the end of February:

Fueled by DOGE and companies like Meta emphasizing efficiency, more people are landing themselves on the market than ever. So that’s the supply side of job seekers: way up.

On the demand side, things aren’t any better. Things are flat. January started off on a high note with AI companies and teams hiring like crazy, but February and March took a turn for the worse.

Now, the number of PM jobs open is just the same as last year, still way below the highs:

And you see a similar trend broadly across technology. This means that candidates are still in a very employer-favorable market.


Proven Strategies » Advice

In employer-favorable markets, the advice you receive in books or older sources just doesn’t work. That’s why I wanted to get you proven strategies from people who are finding jobs in this market.

Spoiler alert:

  • No one used a standard framework for case studies from books

  • Not one of the five got a job offer from spraying and praying their resume

Yet, every single one of these 5 managed to get a job that they love.


Continue Reading Online


Today’s Post

I’m profiling 5 folks who have successfully gotten jobs in today’s insane market:

  1. 5 profiles:

    • Mid-Career Growth PM

    • 🔒 Director of Demand Gen

    • 🔒 Aspiring PM (Student)

    • 🔒 Eng to PM

    • 🔒 VP of PM

  2. 🔒 Key lessons for 2025 job searches

  3. 🔒 Most common mistakes I see in people I advise


Profile 1 - Mid-Career Growth PM

Let’s begin with Alex Wald, now a senior PM who is loving life at Optimizely.

I was sick of spraying and praying my application. You have this post ‘how to get interviews,’ and I really liked how tactically it laid out what I should do everyday.

Profile photo of Alex Wald

Here’s his story…

When Alex lived in Denver, Colorado, he grew from an Analyst at Ovative to Product Manager at Artifact Uprising.

He then joined Signpost as a Senior PM of Growth, but the company unfortunately dissolved.

Left without a job, he travelled the world and conducted two job searches. First, he searched in Singapore.

There, he mastered getting a job in Singapore:

  1. He would go to meetups, meet people, and get referrals

  2. He would help people in his network get referrals using his network, which led to referrals in return

He landed a growth PM job in Singapore.

But he was going to earn 1/2 has much as he did in the US.

So he decided to move to Minneapolis.

There, he tried the Singapore approach, he even tried the spray and pray approach with customized resumes.

But he wasn’t getting results.

Job searching in Minneapolis was not like Singapore.

In particular, Alex really wanted to work at certain awesome companies (the ‘small market’ strategy).

Not rely on what job opportunities might come available via job boards and networks.

So Alex decided to take up my advice and started building work products.

He used Apollo.io to find someone’s email, then emailed them a video.

He would introduce himself, make a recommendation for onboarding process or talk about a time he tackled a similar problem in the past.

He would send one out per day. Each. And. Every. Day. And it worked!

He ended up getting 2 job offers. He negotiated them and chose Optimizely, a company that was in his target list of awesome options.

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Key Takeaways

  1. Adopt your job search to your market - referrals might work in one, and work products in another

  2. You can get a job at your next dream employer even after a career break - just put in the time for work products

  3. Make a little bit of progress every day - Alex built systems to keep him moving forward everyday


Profile 2 - Director of Demand Gen

Even though I often label things for PMs, let’s move into a growth candidate who used my advice to land herself 2 offers.

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