Your career is not a ladder, it's a game. Those who treat it like ladder will make linear progress at best and let their fear hold them back. Those who treat it like a game will collect the resources, find the people, and build the skills that compound — and have fun doing it!
I still hold the strong opinion that every company should have a team that teaches new hires how to be experts in the primary tools used at the company (e.g. Gmail, Slack, Docs, Jira, Notion). And I'm not talking a few keyboard shortcuts here and there. I'm talking top 1%.
Timing is everything.
I ran a 100-person product team at Square and believe fintech was the best place to be in the last decade.
When I decided to leave, I evaluated 20+ industries.
To my surprise, I landed in martech.
Here's why martech is about to have its "fintech moment":
Learned the new "status" job for college grads is VC. This is wild to me. Call me old-fashioned, but have always recommended building something first to understand the fundamentals. Then move into PM if the next level of abstraction is interesting. Investing is level after that.
A simple mistake many PMs make is thinking the product = the UI. Every touchpoint matters — website, emails, ads, reviews, support calls. You need to care about everything that impacts how your customer perceives or interacts with your product (even when you aren't responsible).
Today marks 4 years at Square. It is absolutely wild to think it's been that long and that this company took a bet on me back then. I often get asked why I'm still here. There are a lot of reasons. But it comes back to our sellers. Here's a story from this year that sums it up...
Life update: I'm joining
@stripe
as Head of Product for Merchant Experiences!
That just means if you have feedback about Stripe Dashboard (or the mobile apps), you can complain directly to me now :)
Beyond excited to level up the craft, beauty, and quality with this crazy team.
Wife: can I say something?
Me: okay...
Wife: our gov is failing us. we need the next president to be a product manager.
Me: are you saying I should run?
Wife: no, like a good product manager.
My favorite original
@Square
value was "Give it soul" — I'll never forget it. Square gave me everything. And I gave it everything.
After 5 years of building soulful products and teams, it's time for me to go back to square one.
Jensen's fireside chat at Stripe Sessions is a rare instance where it feels like he's just telling stories about how he views things. A few standout points:
This is such a good example of paying it forward. The CTO of Shopify saw a tweet from an up and coming founder (
@Austen
), wanted to help him, and decided to post his response online for everyone to see. Wish more people did this.
Observations after week 1 at Stripe:
- mission is palpable
- people are ambitious yet humble
- onboarding is impressive
- internal tooling is insane
- there’s so much to do!!
New life achievement unlocked!
Wife is an engineer. PM at her company said they should start using this PRD template other teams have been using.
It was my PRD template.
I rarely get to see her that annoyed. I have successfully infiltrated her work life 😂
My PRD template is getting a lot of share requests all of a sudden. Curious if it was featured somewhere recently?
If anyone knows, let me know. I have some updates to it.
Product managers often ask for more time for "strategic thinking". The reality I've come to is that no one will give you that time. You need to proactively set time aside (literally on your calendar). You need multi hour blocks that you won't cheat on.
Common complaint: "My team isn't moving fast enough!"
Common response: "We need a better tool to track our work."
It's almost never the tool. It's almost always the process. The pace of development will match the clarity of the priorities.
The reaction someone has when you share something you worked on says a lot about the culture
1/ wait...why wasn't I included earlier? who told you to work on this?
2/ woah...this is awesome! thanks for tackling. can i help?
So many of my calls with students revolve around breaking into PM. I know three ways that work for different types of people:
🏢 join APM program
🚀 join startup and hustle (me)
🦎 switch from adjacent role
There is surprisingly little online - might write something
This excerpt from
@patio11
on Dwarkesh can explain most confusing things in life.
The person who does something (but not everything) to help is blamed, while the person who does nothing is not.
Contraversial take (?): most interfaces should be analog / hardware instead of touch
Key offenders:
- refrigerators
- microwaves
- toasters
- remotes
- watches
- safes
Give me real buttons, knobs, switches, and levers!
1/ The old Reid Hofffman saying is "if you aren't embarrassed by the first version of your product, you've launched too late". It still holds today but I want clarify some things I've learned over the years.
As a product organization grows, the scope of a PM or designer tends to become more isolated. This is natural. But there is a dangerous tendency to let that isolation impact how you build product.
This is the Perfect Frame Problem and it stinks 🧵
I don't know what's in the water at AngelList, but I like it:
• Rolling Funds (Feb'20)
• Access Fund (Mar'20)
• Transfers (Sep'20)
• Recurring Transfers (Dec'20)
• Roll Up Vehicles (Mar'21)
• Venture Edu Center (Jun'21)
• No Fee RUVs (Jul'21)
• Deal Partners (Jul'21)
Announcing Deal Partners: Flexible partnerships for modern funds
Funds can now share carry on individual deals with anyone, for identifying great companies & securing an allocation.
It’s a flexible way to add partners to a fund, on a deal-by-deal basis.
I came up with a simple framework to think through this question.
It came down to 3 things:
1. Uneven playing field
2. Neglected user experience
3. Proprietary and valuable data set
Let's break each down.
This framework helped me decide to join Mutiny.
It also convinced the best design leader I knew in fintech to join Mutiny — 👋 🧢
@maccormier
Now we're looking for impact-focused designers and PMs to build an iconic product and team together.
Counterintuitive observation: building something on your own (e.g. site, app) makes you a better product manager more than a better engineer or designer
Wish it was more common for PMs to "pair" like engineers (and increasingly designers). Seeing how someone else thinks and breaks down a problem (in real-time) can be an extremely efficient format of osmosis.
Stripe has built *a lot* in the last few years. But the Dashboard nav didn't keep up. So we did some spring cleaning and I gotta say, it feels nice (especially the lil bounce in the dropdowns).
Much more to come across the Dashboard but if you have any feedback, shoot me a DM.
So that's why I love working at Square. That's why I've worked so hard the past 4 years. And why I will continue to pour my heart into this company.
Small businesses are perfect.
2015: i’m not ready for kids
2016: first kid, first girl
2019: second kid, second girl
2020: we're done
2021: we’re done…
2022: we're done…?
2023 (today): third kid, third girl
i’m one lucky dad 🥰
@shreyas
There are times for pragmatism. There are times for boldness. Don't let the pragmatic decisions of today deflate the boldness of your designs for tomorrow. We need design to always aim higher.
PRD template for those who haven't seen it before.
Caveats:
- I have a few updates planned later this year
- does not apply to every type of product
- should evolve with the project
- etc...
My path as a PM:
- McDs cashier @ 21 ($9.75/hr)
- PM intern @ 22 ($4.5K/mo)
- Math tutor @ 23 ($25/hr)
- Sold first co @ 24 (Got the 💰)
- First PM job @ 26 ($100K)
- Shopify PM @ 27 (📈)
- Snap PM @ 31
No such thing as timeline for life. Your journey is defined by only you.
Every time I see the Nike principles I think "I should hang those on my wall". Then I get too lazy to find a frame. So I finally decided to just print and tape it to my wall.
They are so good and somehow always timely.
at some point in time every b2b saas product is tempted to build a “dashboard” that is a feed of everything you need to do (a magical todo list if you will). this is a trap! users don’t want it and it’s a massive waste of your time. it’s just a nice ego stroke.
If I ever manage to start and grow a company beyond 100 people, I want to hire a Head of Learning. Unlike typical L&D, they will be responsible for teaching people *how to learn*, not what to learn. They will teach system, not content. They will be part of every onboarding.
litmus test: if you are a pm, and your design partner isn't the first person you want to jam with on a new problem / idea, you don't have the right relationship
Too many PMs are comfortable interacting with users through “bent glass”. Reading notes and research reports are great. But you need to talk to users yourself. Do both. People hear different things despite the same words being said.
Changelogs are an underused concept outside of engineering. I make one for every PRD. And they always save the day. Why did we make this decision? When did we change that behavior? Who knows more about it? Check the changelog.
The essential job of a PM is to drive clarity.
This applies to the problem, customer, solution, you name it. The common misconception is that the more senior you become, the less you focus on the details. The reality is that you simply get better at changing altitudes/contexts.
I moved (just north of) Austin, TX!
Having grown up in the Midwest, started a career in the Bay Area, and started a family in New York, I am pretty darn excited to plant my roots in a place that feels like it combines the best of each.
Google Tables will be an automatic smash hit
- teams default to G Suite tools today
- intentionally flexible to be "hacked" in diff ways
- no extra $ (bundling economics in action)
- already approved by IT
- familiar UI (even if a bit sterile)
People will dunk but it will work
I am over the moon with our launch of Square KDS today. Kitchen printers haven't evolved for decades. Now restaurants can seamlessly manage orders from anywhere — pickup, delivery, in-person. This couldn't have come at a more important time. So proud of this team.
It's such a weird time in to be a PM in B2B SaaS.
Everyone is expected to build AI into their product, even if the incremental value might be less than another non-AI feature. And everyone is doing variations of the same prompts (draft, summarize, analyze). Still so early.
the problem with caring about the details, is that you start to notice *all* the details, and how many you want to change, but you can't (bc you have limited time and attention), so you live among them, forever
0-1 work is overrated
Too many PMs claim to be good at (or enjoy) 0-1 work. Most haven't done actual 0-1 work or have but not successfully. The majority actually want to do 1-n work, but with more agency. And that's the majority of actual work to be done.
At a certain point in your career, you switch from looking for whatever you can get to you-shaped roles. It’s a privilege but an important transition. It's where your (specific) collective experiences can be applied in the most potent ways. It's where your best work happens.
There's a part of me that feels like the role of product management is undergoing a reshaping, and most leaders likely need to reacclimate themselves with the nuts and bolts of what's possible today to be relevant in a few years
List of "silly" things that make you better in remote cultures
- hyping work on behalf of others
- fixing typos while no one is looking
- witty slack emojis
- zingers in the zoom chat
- random dms to say “you did great”
Situation: This key metric has flatlined.
Bad PM: How can we get it to go back up? Emails?
Good PM: What is wrong with the product / experience?
Do not succumb to Goodhart's law. Focus on the customer.
The person responsible for your employment is not responsible for your career.
Said differently, learn what you can from your manager, but don't expect them to shape you into the person you want to become.
Part of the job as head of product that is never listed on the job description but ends up being crucial to the role is being an emotionally objective countermeasure to the founders (often related to sunken cost). This can be features, people, strategy, or positioning.
what caring about the details looks like
9:20am pm reports “bug” where element has focus ring when clicked that overlaps with hover state background
9:23am eng says “oo lmc — thanks!”
10:37am designer adds context and proposed fix for component
2:51pm eng deploys fix
"if you can see it then we can create an API for it"
This is a *really* powerful concept that is likely to change how a lot of software is thought about / built. It's a sibling to
@Altimor
's metaphor of the Industrial Revolution for software.
UIs as APIs — pay attention
this is thanks to wild work that
@Connor
,
@codeblue87
, &
@vivekgalatage
did at the unique position of the browser layer in the software stack.
we auto create APIs based on structured data from webpages and applications. "if you can see it then we can create an API for it."
One of the hardest (but most needed) parts of developing a good product strategy is the willingness to sit with extreme discomfort and anxiety for an undetermined amount of time
The next decade will be different for fintech.
The winners are named, the upside is capped, and the space has shifted from invention to iteration.
Yet the best talent is still pouring into this space.
Instead, the best talent should be looking for "the next fintech".
He wanted to tell me about the week. He pivoted his entire business to online pickup. He made payroll for all his staff. And he made more sales than the prior week. Then he said those magical words.
"Thank you"
When you start a new job, you're usually assigned an "onboarding buddy". One of the most overlooked values of this person is a behavioral barometer.
When the CEO says something, how serious are they? When a meeting has no agenda or action items, is that normal?
First, some context on what happened in fintech.
Let's rewind to 2010.
- No trust in financial institutions
- The space was fragmented
- Tools were antiquated
- Brands were bland
- Talent was sparse
Payments and banking were where innovation and creativity went to die.
Every PM needs to launch something without using any templates (e.g. PRD, launch plans).
I get why PMs early in their career want them. They think the structure is the secret. But you need to go through the raw shaping yourself to get any real value from a template.
ugh there are too many things about the website to like
figma tabs for other products
dock for other design apps (swoon)
drawing a button that becomes the actual cta
galaxy background swapping to cta on hover
share linking to twitter and careers page
Engineers learn how to navigate text editors using only the keyboard so the operation of the tool doesn't interfere with their thought process.
PMs should do the same with Google Docs (Cmd+1/2/3 for heading, Cmd+8 for list, Cmd+M for comment, Opt+Shift+<> to highlight).
1. Uneven playing field
OLD: Restrict growth eng to tech giants like Uber, leaving the rest to cobble 90+ tools to convert their marketing spend into revenue.
MUTINY: Bring the power of growth engineering to anyone with no-code tech.
Mutiny is making everyone good at growth.
The best product teams are on a road trip together 🚗💨 Everyone has a shared destination in mind. Everyone gets a chance to drive. Let's dig into what a great trip looks like ↓
An odd trend I've noticed is that we trained (and rewarded) people to "ask good questions" so much that many just stop there, and forget the job is to also answer the questions.
This is especially pronounced in managers / leaders.
building something people want and building a business that wins are different things at the end of the day. a lot of confusion and disappointment stems from thinking they are the same.
I have an increasingly different definition of product management than the norm.
The role of a PM is to maximize the potential of their team (in service of the customer and business).
The main problem I see with JTBD is teams using them to rephrase tasks. They are useful in framing what a team should solve, but detrimental at lower altitudes.
I promise you there is no JTBD to make a button easier to find.