The Product Leadership Job Search: Real Life Context and What One Product Leader Learned about Solopreneurship

So many product leaders want to pursue solopreneurship. Here's what one product leader (Eugene Segal) experienced and the reality of product leadership job searching in this market.

The product leadership job search is hard. The mid-level product leadership job search is even harder.

Mid-level product leaders have been crunched:

This phenomena is known as the ‘mid-level leadership trap’. And it is real.

Here’s what happened:

1. Many product leaders developed as the field grew quickly

2. Since then, the field has cut many of the early leadership positions (think Meta)

3. So, the demand of open mid-level PM leader roles is lower than the supply of high-quality candidates.

The result? As a Group PM, Head of, or Director… many are finding it challenging to stand out for leadership roles.

All the while, accepting IC positions can feel like a down-level—in title and compensation.

What’s a product leader to do in this market?

---

A Real Case Study

You all loved my real case studies of successful job searchers three weeks ago. Today, we’re going to break down the realities of an in-progress job searcher.

This is someone who is feeling the pains of the mid-level leadership trap.

And we’ll explain how he’s overcoming them.

---

Introducing Eugene

Eugene Segal led Miro’s Product Retention group (having worked with former newsletter guest Kate Syuma).

He also writes thegrowthloop.io newsletter and is on the lookout for new opportunities.

With >10 years in product, his job search mirrors what many product leaders are facing today.

---

Why are we writing this piece?

For anyone out there job hunting, it’s a sh*t journey—full of self-doubt, fear, and uncertainty.

That’s why we wanted to share Eugene’s real and raw experience—and the lessons he’s gathered along the way.

Lessons that we genuinely believe will help you make it to the other side. ❤️

---

Today’s Post

Words: 3,976 | Est. Reading Time: 18 mins

1. The Reality: Is Solopreneurship For You?

2. The Job Search Stats: How It’s Gone

3. Eugene’s Lessons:

   • The Importance of Candidate-Market Fit

   • What Job Search Timelines Look Like

   • The Importance of Overdelivery

   • How to Build Pipeline

   • Your Mental State

4. Market Intel on the Product Leadership Job Search:

   • 30 Questions Most Asked

   • The Common Process

5. Answers to Common Questions

---

1. The Reality: Is Solopreneurship For You?

After leaving Miro, Eugene was hungry to explore different career options within the Product realm:

I wanted to try teaching, writing, and advising to see how I felt about each. I felt that I owed it to myself, as I had been working 10+ years nonstop.

So, like many others, he treated this new phase as an experiment, giving himself a 12—to 18-month window to explore.

As he got closer to the 12-month mark, three hard facts became clear:

1. Solopreneurs have to produce content

2. Solopreneurship is lonely

3. Soloporeneurship ≠ PM

Truth 1 - As a solopreneur, you have to become a content production machine

To succeed as a solopreneur, you must build a pipeline.

That is done mainly through content plays at scale, whether it’s LinkedIn, YouTube, Substack, partnerships, or writing a book.

To make content at scale work, passion for content generation is key, as this task will consume most of your time and energy.

Posting a write-up once every two weeks won’t cut it to build a healthy pipeline.

Truth 2 - Solopreneurship is a lonely journey

You’re not part of a team, so there are no co-workers with whom to build deep, genuine relationships.

Most of the day, it’s just you and your Mac/PC.

If you thrive on solving problems in a team setting, you might find the solopreneur path challenging, isolating, and quite depressing.

Truth 3 - As a solopreneur, you are not building products.

PMs like Eugene tend be builders at heart.

While some might say that advising allows you to help others build, you’re still not building with your own hands.

That’s the part Eugene missed the most.

So after scratching the itch of solopreneurship, he was ready to return to the PM leadership job market…

---

2. The Job Search Stats

Eugene has seen stats that are very typical:

During the last four months, Eugene dropped 50 applications with:

• 30 non-responses

• 7 initial contact followed by ghosting

• 18 interviews

Of those interviews:

• 40% didn’t pass the early stages (e.g., Dynatrace)

• 20% hired someone else before Eugene reached the final stage (e.g., ZoomInfo)

• 20% stopped hiring for the role for internal reasons (e.g., Canva)

• 20% Felt were not fit for skill after a few initial chats (e.g., Viber, Monzo, Zalando)

• He reached the final stage at three companies: director-level roles at Monday.com and Autodesk and the first PLG hire at Deel (IC level), but they ultimately chose another candidate

As Eugene said:

These ‘almost got the job’ situations hurt the most, especially after investing significant time and effort, eg over three months… 😥

He got one offer, which he declined (VP Product role at a B2B SaaS startup).

Why did he decline? The total compensation at the offer stage didn’t match what had been discussed earlier. There was a 35% gap in the base salary and a significant difference in both the equity amount and terms.

So, he’s still on the job market.

Many of you will be able to empathize.

---

3. Eugene’s Lessons

So what has Eugene learned from this process?

Here’s all the juicy details.