Aakash Gupta Profile picture
May 2 10 tweets 2 min read Read on X
The product leadership job search is completely unlike the IC PM search.

Here's what you need to know:

(That most people don't) Image
My collaborator (and 3x Sr Dir of Product) @xolin and I talked to:

• 7 external executive recruiters
• 2 internal big tech executive recruiters
• 2 VC talent teams
• And 10 CPOs and VPs

To learn these 5 things:
1. Less and less jobs get listed

At the Group PM and Principal PM level, 90%+ of jobs are still listed on job boards.

But as you move up, those numbers drop considerably:

• 50-70% of (Sr) Director and Head Of roles
• 20-50% of SVP and VP roles
• <20% of top exec roles
This means that your strategy has to change entirely.

FROM: Reaching out to listed jobs

TO: Finding unlisted jobs, and also becoming a magnet for one's you don't
2. There's a huge difference between early product leaders and top execs

One of the biggest misconceptions is all levels of the product leadership job search are the same.

But it's critical whether you are the top, number 2, number 3, or just nth product leader.
3. The process takes longer

While an average principal or Group PM role can get filled in 1 month, more senior roles take longer.

Companies might take up to 6 months to hire a top product executive, even with the help of executive search firms and VCs.
4. Retained search firms and VCs drive placement at the top

The two channels that drive the most placements for the most senior roles are not applications or internal recruiters.

They're personas most PMs aren't used to: retained search firms and VCs.
How do you engage these folks?

• Retained search firms: you want to build lifelong relationships with individuals at these firms, helping them before they help you

• VCs: you want to keep active relationships with top VC partners in your industry niche and the top VC firms
5. Compensation goes hyperbolic at the top

And it's worth going after these gated roles (if you're qualified). Because the compensation goes hyperbolic.

It's that equity part, especially. Top executives might have cash comp of 2x Group PMs but equity worth 20x.
SUMMARY:

1. Less and less jobs get unlisted
2. There's a huge difference between early product leader and top executive
3. The process takes longer
4. Retained search firms drive placement at the top
5. Compensation goes hyperbolic at the top

• • •

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More from @aakashg0

Apr 18
2 rules govern how much you can make:

Stage and success of company

Let me explain 🧵 Image
Factor 1 - Where You Work

At bigger companies, the same title earns a lot more. Take VPs:

• $10M rev/ Series A: TC $675K
• $100M rev/ Series E: TC: $750K
• $500M rev/ Series E: TC $750K
• $1B rev/ Small-Mid Cap: TC $950K
• $100B rev/ FAANG-like: TC > $2.15M
And there's a huge difference in how liquid the earnings are at these companies.

For most private companies, liquidity events are rare and capped.

Moreover, the outcomes are highly bi-modal: the equity could go to 1, or could be a multiple. It's hardly a certain thing.
Read 9 tweets
Mar 29
Remember the days of unlimited music skips on Spotify's free tier?

I bet you didn't know removing it increased paid subscribers 25%.

Here's the story: Image
Unlimited skips on the free plan was a golden age for music lovers.

But, for Spotify, they were losing money on each of those customers.

They needed them to upgrade.
So in 2014, Spotify limited skips on the free tier to six per hour.

The headlines were

• "Spotify’s free tier just got worse"
• "I’m quitting Spotify"
Read 6 tweets
Mar 27
I researched the pricing models of 50 leading consumer software companies.

These are my top 4 takeaways: Image
1 — Subscriptions have come to every industry

In every industry, it's worth considering if a subscription makes sense for you.

Recurring revenue, stable cash flow, and higher LTV are all potential prizes.

But, consumers might be annoyed.
2 — Subscriptions aren't the only game in town

Yes, subscription or “subscription-like” pricing is 56% of this list.

But options like one-time fee, ad-supported, and transaction-based also appear.

And consumers often prefer them.
Read 6 tweets
Mar 25
Companies kill their own messaging over time.

4 bad habits seep in as they grow.

Here's the breakdown: Image
@apierriPMM Bad Habit 1 - Speaking to multiple audiences at once

In the world of growth-focused companies, prioritization can be seen as weak.

But instead of effectively speaking to multiple audiences at once, you end up speaking to none.

In messaging, you must prioritize.
Bad Habit 2 — Choosing the Wrong Champion

Most commonly, people aim too senior. This has 2 problems:

1. There are exponentially fewer CEOs than VPs, directors, & managers
2. CEOs aren’t buying software

(There is one exception: if you’re targeting a small business.)
Read 7 tweets
Mar 9
You know ChatGPT. But you don't know the history of AI.

Here's the key events you need to know: Image
1956 -- Dartmouth Conference:

• Academics gathered at Dartmouth. They used the term AI for the first time
• The idea was to build a machine that mimicked human reasoning
• The first model was created
1958 -- Perceptron:

• Frank Rosenblatt's released the very first neural network, called Perceptron
• It was a single layer, but laid the foundation for architectures to come
• It was an early model of supervised learning
Read 15 tweets
Jan 18
Notion's $10B valuation isn't magic. It's a masterclass in PLG.

There's 7 key elements to this motion.

Here's a quick rundown of each ↓ Image
1. Core problem communication

Clear & cute messaging:

↳ Notion has its trademark cartoon style
↳ And it always pays close attention to the details of design

Community to get the word out:
↳ Notion's creators and users spread the word
↳ It adds fuel to the fire
2. Information for decision

Plans for all:

↳ Its freemium forever plan attracts the price sensitive
↳ But it has all the functionality a big enterprise would need

Differentiation:

↳ Notion has great templates
↳ Notion is structure free, so it can be anything
Read 9 tweets

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