It was painful going through the enterprise focus transition along with a nonsensical reorg imposed by the aforementioned Big Tech VP. One day we had focused platform-specific teams working on satisfying customers, the next we were moved to cross-functional feature teams and focused on enterprise features that (from our perspective) no one ever asked for.
I also felt the sting from mediocre engineering managers. I remember sitting down with Tracy and Ralph at Uptown Bar and giving them both barrels on what I thought of several managers. To their credit those managers weren't working there very long after that conversation.
IIRC Ralph asked if I wanted to move to being a manager and I declined but in hindsight I think that was a mistake - we needed good management in engineering more than we needed my code.
Another thing that hurt us was hiring a bunch of PMs. Most of them were condescending, ignorant, or both... but suddenly they were telling the engineers who had built everything what to do? IIRC we could have cut that department down to two people with no loss.
The leader of this product team was a manager that just didn't seem to be doing his job, only pushing paperwork and giving scatterbrained presentations. I never did find out why he was kept on so long. I think I very cheekily asked Tracy one time which of his relatives worked at Y2K or Sequoia such that he couldn't be fired because it was clear everyone in engineering was fed up with his nonsense. I'm pretty sure at least several top engineers quit due to that guy specifically.
Either way I don't regret my time at PlanGrid. It was a great team and I'm proud of what the team did and what I did.
The best PMs I know operate like CEOs in the sense that it's someone's job to scrub the toilets, and until you figure out how to afford/hire someone to do that for you ... you're scrubbing the toilets yourself. Someone has too!
The 0% interest free capital environment distorted the PM role though, especially in land grab cultures. Imagine having enough budget to hire a 4-6 person squad of toilet scrubbers (and golden toilet) so why ever clean it yourself?
So sorry for the crappy metaphor, but that's why I believe PMs are on the chopping block right now. Not because there's something intrinsically not-valuable about the role. From the perspective of Tech Lead / Staff Eng in a Big Tech Co, good PMs created clarity and helped my team(s) execute. The worst PMs created ambiguity, and the worst of the worst pushed ambiguity+responsibility down as far as they could.
I think of them as basically glue. They just help make shit get done. That could be helping co-ordinate between eng and design, doing customer research, managing expectations, etc. Whole range of things that different PMs do.
but with that kind of role, contribution quality is rarely assed correctly, and at the same time, the sandwhich role between contributors, management, and customers, combined with a usually communication-savvy skillset can be extremely dangerous. even worse in impact than a highly visible „bad“ EVP/SVP.
If not for the PM, who will speak with the customers, gather, analyze and understand their needs and problems?
There should be a person that drives the product in the right direction based on customer conversations.
In the early stages founder is the product owner.
But as the company grows, the role of the founder/CEO changes. You now build the people, and people build the business.
Engineers or CEOs building features no one asked for is IMHO one of the major reasons lots of tech startups fail.
Awesome idea, cool product, but no one asked for that feature you were building for 2 months. (guilty here myself)
1. "Hey, I am picking up my kid from preschool, so cover (my only 15 minute meeting of the day)". This is a mandatory future present in 80% of scrum masters.
2. Team, good job, I am so proud of what you have accomplished - I, for one, am always looking for the approval of a random person who has little to do with the team.
3. "Well, what do YOU think we should do"? "Thank you for your input! Let's remove those blockers. Go ahead and reach out to whoever the relevant person is!"
4. Key knowledge required: Daily standup, retro, planning meeting run by dev.
Did I miss anything?
It's been a while - we should catch up soon :)
Their bathroom is fun
Most of us have been there in the painfull all-hands meeting falling asleep because the more people you have, the less they will care about the business. In a a team of 5, I have a lot of skin in the game and also a lot of influence. In a company with 100K employees, most of us are just a cog and some cogs don't even move anything!
PlanGrid is B2B SaaS.
Next is what I found most people doing differently from my ideal - abstract and refactor base on your existing implementation, not because of some framework doing it, nor because the previous project did it this way. Do you need a data access layer, a library, a folder, to talk to database where the first implementation was just storing things as a variable? You probably need a database and plain SQL. Do you need site reliability engineer to keep your site online while your traffic all comes from friends? Do you need a QA for testing? Or do you need a product manager where, as a founder, the value proposition has yet to be proven? How often do you see a code base spinning up all the folders/empty files because "we may need it". And how often when you hire someone, they spin up various incarnation people * time like teams, sprints, squad, function, BEFORE understanding the current implementation. This is why you hire the wrong people. And you know it only 1 year down the road. Wrong abstraction. Using framework has its appeal, where a cookie cutter solution mostly work. But it also has its limitation, bloat.
Once a wrong abstraction is in place, the more code/people depends on it, the more effort it takes to refactor
Theoretically applying all of those requirements to your product might make your product more secure, scalable, or reliable. It'll also make your product harder to maintain, harder to test, and harder to improve.
Many of those requirements are there because vendors put them there. If you're part of the RFP process (and you should be if you're actually selling to that sort of customer) you should be actively pushing back on requirements that you feel are pointless...making them optional instead of required, or at the very least providing a delivery date instead of delivering day 1.
In the enterprise space there's no guarantee you'll get the contract; to an extent the decision more political than technical. You should do a brutal assessment of your actual chances before engaging in any work implementing their requirements before the contract is signed. And since the sales cycle will be at least 6-9 months you'll have plenty of time to figure things out.
Lastly, if your product is highly desired the "requirements" can be bent or delayed. They're guidelines and can be overridden, if you have the right relationships.
In point one they list this. In point 3 he mentions his biggest mistake was hiring someone with starpower from a public company who didn't work.
Unless the founder is an A player in terms of recruiting everyone hired would be a C player or less. And in point 3 we learn he is not an A player.
How do B players ever get hired?
(Added: My Ph.D. in mathematics is useful for something.)
A player wants to hire A players so the A player can more effectively beat their rivals in the marketplace.
B player wants to hire C players so the B player can more effectively beat their rivals in the company.
An A player will still make hiring mistakes but they have the skills/ability/aura/whatever to convince other A players to come work with them.
Many A players won't want to work for/with a B or C player because they won't see this as a good opportunity.
Not sure if they actually meant that B players can't hire B players but maybe. This sort of framing is pretty high level though.
It’s not as easy as A and B and C people (or any other labels).
I’ve professionally led a team doing physical labor, and currently a team of teams doing intellectual labor (software development) and several between. They have been excellent, productive and profitable as well as respectful, ethical and honorable.
The reasons behind their success are complicated but always start on the same foundation: respect. Genuine, difficult to come by, and more difficult to maintain, respect. For the customer. For the user. For each other. For other departments. For the community. For the competition.
From there builds trust, and from trust comes ambition and the ability to focus on the purpose of the job (yes, it’s a job in most cases, not a mission or vision).
This is what I see some growth CEOs miss. They lack respect for people outside the “right” mold and don’t hire (or keep) them. Then to their surprise, their teams become dysfunctional.
Many tired anecdotes teach us about this (too many chefs, etc.) yet the same mistake is made with relentless repetition.
I'm currently knee-deep in the enterprise world, and trust me, the point about selling into these orgs is very true. My team just spent the last year moving our client off a Salesforce Lightning-based solution onto our custom-built one. No one in the org could tell us why they chose to build it in Lightning, but everyone now says they love our solution.
The lessons you learn building a startup are good and always usable, but you need to be ready to learn what it's like to work in and with an enterprise, to figure out how to adapt and sell your product to them. It's an arduous process, but worthwhile.
I have been lucky to work in a field where teams frequently work in parallel and success or failure is pretty clear cut. And teams are often stratified based on the priority of project. Many times-- not always -- the "B" team crushes the "A" team. Why? Some reasons include: the A team is performative and focused on the things that burnish the careers and reputation of its members. B teams have more of a sense of the wolf being at the door and that if they don't perform their task they will feel the consequence. Being underdogs promotes teamwork.
Obviously people have profound differences in their strengths and weaknesses and some people are completely inappropriate. But calling people stars or A player covers up a lot of lazy thinking that includes a lot of bias. I have worked at smaller startups that say "we only hire A players". Obviously that is delusional but worse it covered up the more profound questions. Why did you hire the wrong person? Why did that person or team fail?
Fit matters. You wouldn't hire Jim Carey for a DiCaprio role.
The corollary is: find out where you thrive and go there.
Don't beat yourself up if you get spun out of a FAANG, or a startup or a smallco or a bootstrap or a founding role or a mid-tier enterprise. Don't contort to a role or company that isn't a fit.
If you have solid skills, you can find a place.
I joined my current company when it was 40 people (and around 10 developers). Almost 6 years later we're ~1500 and the engineering org is something like 200-300. I think I was most comfortable around 20 or so developers but that doesn't mean I can't make continue to have meaningful impact now that there's an order of magnitude more people and the org has completely changed.
I've seen folks who were supposedly "A player"s from small start-ups and FAANG join the company at different stages. Some succeed and some fail but I never noticed any correlation between current size of the company they're currently thriving at and our size when they joined.
Fit is never going to be perfect so don't give up on something just because it might be a little uncomfortable. Give up if you've tried to make it work and it's clear you can't find a way to have impact.
It's clear you don't understand what A and B people are then. If the "B team" is crushing the "A Team", then they aren't the "B team". Also, notice how you switched "player" with "team"? The quote is "A players hire A players", not "team".
The point is that top tier individuals typically hire top tier individuals. The reason this notion isn't so clear cut is because its hard to identify A players before the fact. It's a retrospective truthism.
After spending multiple paragraphs about how they found that they had to dig much deeper into the background of every exec, getting 10+ references from reports, peers, and their managers, and developing specific lists of red flags . . .they end the section with: "Takeaway: Always trust your gut on people. "
Yes, for sure, if you 'gut' tells you something is off about someone, seriously consider and trust that also, but what was really effective was not gut-trusting, but gathering more hard data and observations to evaluate.
Just seems like the author didn't really think it through.
I'm also a bit surprised that she's throwing the "big company executive" under the bus here, given that it's very easy to identify who this is. She doesn't seem to be merely saying that the fit was the issue, given this:
> 1. They frequently use the wrong pronoun “I” followed by “[contribution to the company]”.
> 2. You dread having 1-1s with them.
> 3. They blame you or their peers.
> 4. They complain laterally and downwards.
If that is the case, how do the B people get jobs in the first place? Who hires them?
Additionally, people who are not so good tend to be threatened by good people. So they will rather hire someone that won't threaten or "find them out". B hires C.
Once you get large enough your ability to really selectively recruit gets a lot harder when natural attrition means you need to replace X amount of people just to continue operating as before.
Of course earlier on, the fewer the people the larger the impact each one will have so just like the article says about transitioning to enterprise, the focus and requirements of the HR team change as well.
https://tracy.posthaven.com/part-i-founder-led-enterprise-sa...
Again, I get that the VC-backed status doesn't allow this, but that's such an interesting distinction - this would be a successful $50mill ARR business if not VC-backed, but since it is, the panic button is pressed and that thus leads to decisions and scrambling that upend a lot of what was working.
Guess we all (as usual) need to make decisions about capital sources early and how we want to grow, as well as the real trade-offs between those choices.
I'd argue that ARR is still a good measure just not the growth at all costs, w/e it takes to get toe 100M ARR/Unicorn status anymore. After all, sales is sales and if you don't have repeatable sales you probably don't have much of anything.
> After all, sales is sales and if you don't have repeatable sales you probably don't have much of anything.
That's right, but you're missing the key that it's a necessary, but not sufficient requirement. When the pool of investments is 90% with ARR are honest and straightforward, then it's good to use ARR as a metric. But when the pool changes to 50% or less who are honest (as Goodhart would predict), the metric loses value.
> Being at a startup is hard in a way that is almost indescribable to anyone who hasn’t experienced it.
Being at a startup as an employee isn't necessarily hard. You hear this type of "startup is so hard" because running companies well is hard and successful startups will often grow faster than their founders are able to grow their own ability to run companies, which makes their own job challenging. And a lot of startups are poorly run in ways that are entirely avoidable (often as a result of their CEOs not being able to grow as quickly as their company) which can make life hard for the employees as well. But this isn't a necessary part of the startup experience.
Of course not - in many cases, things get drastically more difficult. Instead of being able to pursue a clear vision, you often have to deal with tons of inter-organizational politics. You have all these extra stakeholders that are trying to influence you, some with good intent, others not so much. More processes need to be imposed, there's more pressure for standardization/integration both in terms of the product features, implementation, not to mention processes.
And this is about apples to apples it gets.
Another way to think about this is that there's a reason why startups are successful despite the massive advantages incumbents and larger companies enjoy. It's because certain things are harder at bigger companies. Then how could it be that being at a startup is uniformly harder? Startups exist in large part because they are more efficient or make things easier. If you flip that around, it means trying to do some of those same things at a big established company can be objectively harder.
Contrast this with startup companies, where it's often required to explore and build completely new things from the thin air of the ether. I'm not saying other jobs don't also have elements of this, as new projects and opportunities do emerge, but being at a startup is definitely an extreme situation and arguably a different game. In the meta lens, it can be viewed as the act of mining the veins of market realities for golden ideas.
It's for the risk takers and adventurers. I've witnessed many a great engineer learn it's too undefined which can be uncomfortable, and is not a good fit for them.
It's nothing personal, along the exact same lines as some folks who can't stand working for a large company.
Different strokes and all that. This form of diversity is one of the beautiful things about the spectrum of humanity. In aggregate, it works!
A lot of these types of statements generally are made by founders whose relative role at the startup (C-level) is much senior than their past or would-be role at larger companies (entry-level or close). Or early employees who got to be much more senior within a startup than they had been at a larger company. This just isn't an accurate statement for the rank & file or when you compare people at similar levels across companies.
Seen it SO many times when startups decide they need "grownups" in big positions to be credible externally
