Aakash Gupta is a product leader turned author and professional newsletter writer, with a huge following on LinkedIn and Twitter. He writes regularly on product management principles, and personal and career growth and recently put out an article about nailing the product leadership job search. We also recently collaborated on an article about fractional product leadership! In this interview, I spoke to Aakash about his journey into full-time content creation and some of the lessons he learned about the product leadership job search.

Episode highlights:

1. The product leadership job market is slowly coming back to life

It's been tough out there, and loads of amazing people have been laid off and struggled to find new roles. Some might doubt they'll ever get another job again! But there are good and great jobs available if you know where to look.

2. Many of the best jobs aren't advertised in public and relationshps are everything

There's a "dark web" of networking and personal relationships, without which you might struggle to get introduced to some of the jobs. At the highest level, the majority of jobs are not posted publicly. Whether you like it or not, you need to play the game and build strategic relationships with boutique recruiters and especially investors.

3. You need to prioritise the type of job you want and it's not all about money

Most people are trying to optimise for something in their new job. Maybe it's a big pay packet. Maybe it's a mission they believe in. Maybe it's the stage of company, influence and impact. There's no wrong answer, but make sure you know what you're getting yourself into and what success looks like.

4. Try to make your career look linear to land the role you want

Many of us have squiggly careers and we've bounced between industries or types of company. This is fine, but if you're looking to get a job in a particular niche then you need to optimise your career narrative to tell a story about why YOU are the person for that niche.

5. Many leaders are still biased towards Big Tech employees, but you can beat the odds

Some founders or business leaders will always prioritise someone with a stellar name on their CV, and this can leave people who have worked for lesser-known companies feeling adrift. However, you can take a strategic view of your job search, outwork and outsmart your competition.

Contact Aakash

You can catch up with Aakash on LinkedIn, or Twitter or check out his newsletter.

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