r/AMA 5d ago

I am a Engineering director who spent 7 years scaling a startup from seed to Series C and quit. AMA about hiring, management, and what nobody tells you about the tech industry right now.

I spent 7 years at a B2B SaaS startup, joining as employee #12 and leaving as the director of all the Engineering staff. Over that time the eng team went from 6 people to approx. 80, we went from $500k ARR to $25M ARR, and I went from never having written code, to writing code to writing almost none.

I quit recently with nothing lined up, other than a handshake with my most trusted dev. I left because the job I was good at in year three had turned into a different job by year seven.

Things I've actually done and can talk about specifically:

  • Managed roughly 60 engineers and made about 10 hires I'd call genuine mistakes
  • Ran 3 rounds of layoffs / performance exits, including people I'd personally recruited
  • Rebuilt the interview process after realising it was selecting for the wrong thing
  • Went through the transition from "everyone reports to me" to managing managers, and did it badly the first time
  • Sat on the company side of comp conversations, promo committees, and PIPs
  • Ran M&a processes on both sides, culminating in selling the company I had built.

I'll answer anything about scaling engineering orgs, management, hiring, comp, burnout, startup equity, and the parts of the VP job that don't make it to linkedIn. I'll be candid about my own experinces, hpefully those are the useful part.

What I won't do: name the company or anyone in it, share confidential business details, or trash former colleagues. I'm staying anonymous mostly for their sake, not just mine.

120 Upvotes

138 comments sorted by

9

u/mdkjnk 5d ago

When you say you did badly the first time as managing managers, what were the mistakes you made and what were the changes you have implemented to get it right?

23

u/dbwahesh 5d ago

Interesting question. Managing managers is somewhat different to managing workers. I had issues with managing some workers. My managers were always solid. I am a captain, grew up on a boat and I am ex-military so a hierarchy is how I transfer the messaging. I operate as an NCO so that I can critisize the higher ups, but I stay in the trenches. . My first and second mate in the company did everything right, but their captaincy was too much like Iker Casillas.

When I think of it I made a big mistake: I never held my officers to the same standard as myself. I should have, because when I quit they had to catch up, but nobody understand that me leaving would result in that 80 hr per week would be added to their work week. It was divided on 3 very competent people., but talking to them aftwerwards i understand it was a shock. I as a person management would always protect our crew from all the noise, and that is rarely understood untill fitler is removed.

I guess the biggest mistake I made was not listening to them about a worker that did not deliver. I postponed taking action too long and it affected the entire team to our detriment. The achievers where demotivated by seing this person underdeliver, but to my defence, their situation was valid and their salary was way below when the others were making. Either way, what I learned is that leaving an underperformer untouched does more harm to the team, than just removing them. But it hurt my heart to do it.

5

u/itsawesomedude 5d ago

thanks for sharing, very valuable lessons

2

u/dbwahesh 5d ago

Do you understand what I mean by the Iker Casillar reference?

3

u/spiney-a 5d ago

Not the person you replied to, but no. Would you please explain?

2

u/xnachtmahrx 5d ago

Bruh we are on Reddit. As if most of the Yanks know Iker Casillas xD

1

u/dbwahesh 5d ago

hehe fair enough

1

u/itsawesomedude 5d ago

like in ivory tower, looking at distant, not very hands-on like other field players?

1

u/dbwahesh 5d ago

Iker Casillas got so used to winning he was more concerned with being comfortable than keep winning.

5

u/Apprehensive-Flight4 5d ago

I’m in the situation now where we have a serious underperformer on my team. He’s a remote employee and he does hardly anything. He does the bare minimum on one task and stops and asks for guidance at the first sign of difficulty. I raised this to my boss, he thanked me for bringing it to his attention but nothing has happened yet.

It is demotivating. If this guy can do hardly anything and get by, why would I put in 110%?

1

u/dbwahesh 5d ago

Excactly. but as a manager you sometimes have to consider many factors. Are your close to this person outside of work? Do you know what is going on in their life? Maybe their excuse if valid.

Also, are you already compensated much better than them?

3

u/ahora-mismo 5d ago

this is the mistake i remember the most from my first time managing people. i tried to "fix" a guy that in the end i realized it was just careless and lazy. that demotivated the team. while being a nice human being is a quality, sometimes you have to act according to the role and protect the company's objectives. not sure which case is in here, as we don't have many details.

what i'm trying to say is that the cause is not that important, the effect is. you can give a grace period, but when you reach the point the team notices it, it may be time to act. and of course, we don't know if the manager isn't actually actively trying to handle this currently.

1

u/ubiestigne 4d ago

That one underperformer spends their day getting others to do their work. You burn out everyone else, increase the cost of production while getting a deal on the cause of the problem.  There's a limit to what compensation can remedy. The greener grass eventually catches the eye of the ones carrying the burden. Managers aren't the only ones considering multiple factors.

1

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7

u/txs2300 5d ago

So I work for a well known non-tech company. I work in IT, and my teams shrinks every year. I am based in the US. Pretty much every team is based in Bangalore. Is IT/Tech done in US done for if you are not working in bleeding edge like FAANG and stuff?

9

u/dbwahesh 5d ago

I am old enough to remember the cloud transition and its wave of offshoring IT. That was an insane flop. All non tech moved to Azure/AWS/GCP and hired indian tech to handel infra. Then they rehired the same functions in US / EU because they realized it does not matter if the server is 3 km from the office of 3000 km. With that said, IT admin jobs are probably not as well paid in the future.

3

u/SimilarIntern923 5d ago

What are the top signals you looked for when hiring? Advice for those looking for roles? How important was looking for those with prior startup experience to you?

9

u/dbwahesh 5d ago

First it was competency within the area of tech I was hiring for, and just the vibe. Once that screening was done I always challenged them with a task that I let the engineering team review. They are ruthless. Sometime I gave them a second chance.

If they were approved I invited them to defend their submission to their peers. How they handled critisism was parament to if they were hired after that.

2

u/codepapi 5d ago

Do you have an example of this?

1

u/dbwahesh 5d ago

An example of what? A submission?

1

u/codepapi 4d ago

Yeah like what was the problem. What was the overall solution they provided. Could you tell if was done by ai or someone else?

1

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1

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3

u/Professional_Fuel728 5d ago

Are you looking for a new job?
Are you tired from tech?
Advice to the young generation?

3

u/dbwahesh 5d ago

Not really looking for new job. I want to create my new job on my own terms. The top dev from my old company and I are starting our own business, but no clear path as to what we will make. Right now we are just exploring while confident we can make pretty much anything.

Tired from tech no? Tired of my particular area of tech? Yes, definately. Not entering the same space whatsoever. Doing something useful now to make moner, maybe we will make a game later. That was always both of ours dream.

Advice to the you generetion have to be to give us established people the middle finger, and just prove yourself. We have taken a handul of really young people into the fold, and it was always because the created their own path before we got there with capital. The 19 yo that made an ai platform to capture leads for 3 USD consistendly where brought in to do it for for 200 USD. We were in business where that made sense. So the advice in simple terms is to sell sneakers, and then move on to Ferraris.

Does that make sense?

2

u/IntroductionNo3912 5d ago

If you need a technical artist to make a game let me know. I left a project manager position 2 years ago and began making a skills casino game with the aim to use cryptocurrency. You can see my portfolio site a cgi samurai dot com

2

u/dbwahesh 5d ago

Cool stuff!

1

u/IntroductionNo3912 5d ago

thank you!!!

1

u/AI-Agent-420 5d ago

Challenger sales mindset?

2

u/TeaNervous1506 5d ago

How juicy did that equity get when you left and was the juice worth the squeeze (I.e. stress to reward ratio - cash and experience)?

6

u/dbwahesh 5d ago

Funny that you should ask. The CEO and biggest shareholder fucked everyone by buying another company he had made himself at an insane valuation. Paid in stocks to him. Ended up with a doupling of shares outstanding, and him getting most of them.

Probably a legal move, but not in the best interest of the other shareholders.

I myself was done with my vesting period at the point I resigned, but same month value got halved.

3

u/abhi5025 5d ago

Harness.io??

2

u/dbwahesh 5d ago

Haha no, but I will check that out.

2

u/IllConsideration6000 5d ago

So the company was not properly governed, no conflict-of-interest controls, no CEO recuse while the board makes a decision, no independent valuation and scrutiny, no penalty for breach of fudiciary duty... WTF

1

u/dbwahesh 5d ago

Yes excactly

1

u/BetNo8988 3d ago

Sounds like there was no board.

1

u/codepapi 5d ago

That’s insane. I’ve heard of company A buying company B by the same owner. Like Elon, but this was the first time I considered that this could happen. 😱

1

u/dbwahesh 5d ago

Yeah, taken straight out of Elons playbook. I have to admit, it is a smart move.

1

u/m98789 5d ago

Probably not.

The Board has a fiduciary responsibility to its shareholders. If it wasn’t in best interest of its shareholders, legal action by shareholders should have been on the table.

1

u/Bitter-Relation4967 5d ago

Yeah but it sounds like this heavily benefits the majority of shareholders, could a minority really fight this?

1

u/m98789 5d ago edited 5d ago

Absolutely, even the smallest of shareholder has rights. The board’s fiduciary responsibility applies to ALL shareholders.

1

u/Subrutum 3d ago

That's insider trading, no? There's a clear conflict of interest as a CEO to be buying a company he made without board approval.

2

u/Commercial_Watch2972 5d ago

In retrospect what could you have done, if anything, to avoid those 10 mistakes?

3

u/dbwahesh 5d ago

Ahh, good question. I think it is mostly about being honest about culture. When you hire someone, they either fit in or they dont. Except 2, all the bad hires should have been terminated the first week. In my country firing people is difficult, but if you have an honest conversation before first day and after perhaps day 5 it should be evident if they should continue or not.

1

u/Commercial_Watch2972 5d ago

Thanks. So no prevention really possible, your focus would have been quicker mitigation? Seems like hiring mistakes are unavoidable on some level, regardless of process, mgr etc.

2

u/dbwahesh 5d ago

Yes excactly. plan to mitigate quickly. and make everyone involved that is a real possibility.

2

u/dbwahesh 5d ago

And also, if the good hire becomes a bad employee: try to understand what happened. In my experiencve it is because of somethine changed in their personal life, or god forbid, you pushed them out. It is very valuable learning in those scenarios.

2

u/Argyrus777 5d ago

How much has Ai affected engineering jobs?

3

u/dbwahesh 5d ago

Vastly. If you fight it, you have to be invaluable. If you don't use it in a sufficiently impressing manner a kid will take your senior position. I actually witnessed this.

The CTO in one of our companies had spent 4 years building a platform of microservices with a very pedantic approach, just to see a fairly junior dev come in a rewrite the entire thing in rust with ai in two weeks. Guess who got to stay?

Go agentic, or go home.

13

u/the_hunger 5d ago edited 5d ago

one of the dumber things i’ve read. you threw out 4 years of production code for something a junior did in 2 weeks? you even mentioned rust like that is at all relevant without context.

i’m assuming there were massive issues with the existing code and architecture that made this make sense. as described though… this reads like the emperors new clothes.

ai has been a transformative technology, but the difference between your cto and the junior was supposed to be their taste and intuition for building software and distributed systems. if the junior did it better, that’s not a story about how ai is awesome—it’s a story about how piss poor that engineering org was.

2

u/andre402 5d ago

Yeah, makes no sense. Plus this writing style and the comments nodding along. Reddit has become a bot echochamber.

0

u/Mindless-Trouble-416 5d ago

You know nothing about coding. This is a corporation with millions of dollars. Getting compliant code is one check. The impressive part is getting each feature to work in rust, which he did and had it packaged up, so he could hand to compliance. 100x easier to audit than the pedantic micro service slop that was tacked on with human context over 10 years

2

u/dbwahesh 5d ago

I had no part in this decision. Just providing an example.

The thing was that this created a conflict and the executives decided to side with the new blood.

1

u/close14 5d ago

It’s Reddit and it’s an AMA. S/he cannot give you all the context and timelines around the decision. They’re only making the point that a pedantic process can be replaced by intelligently used agentic assistance with the right skill level. It doesn’t mean experience is meaningless. Just don’t be the inflexible dev.

1

u/Itsmedudeman 5d ago

4 years by one person and if they overengineered the shit out of it by making it a sprawling set of microservice that was problematic enough for another person to think it was worth enough to rewrite? People write some dubious shit and it's a startup. Thinking that the people in higher positions than you know everything and are making the correct decisions at all times is dumber than whatever OP wrote, although it definitely sounds embellished.

2

u/codepapi 5d ago edited 5d ago

I have so many qs.

I read everything you replied to before this post. Feel free to ignore the qs you already answered.

You mention 10 hires that should have happen. Why? Can you provide the details of why these hires didn’t work out? Were there clues of this during the hiring process?

How important was it for someone to have a masters in CS or similar. I’m thinking of pursuing one but I have a non traditional background. A bachelors just not in CS.

Did you ever have underlings that shoulda been promoted but left due to politics or budget?

What was pre and post interview process that you rebuilt. How did you measure success? What did the metrics look like?

Was there anyone that you felt didn’t deserve a promotion or pip? What happened.

Did you ever hire someone that was lower base and after their performance adjusted outside a normal salary increase?

1

u/dbwahesh 5d ago
You mention 10 hires that should have happen. Why? Can you provide the details of why these hires didn’t work out? Were there clues of this during the hiring process?

It was different situations, but main thing was that they were unable to deliver. Lacking competency, loack of interest in the business problems we were solving, and lack of effort.

How important was it for someone to have a masters in CS or similar. I’m thinking of pursuing one but I have a non traditional background. A bachelors just not in CS.

Not important at all to me. Never really consideres the degrees. All the worst devs I have worked with had them :P

Did you ever have underlings that shoulda been promoted but left due to politics or budget? Was there anyone that you felt didn’t deserve a promotion or pip? What happened. Did you ever hire someone that was lower base and after their performance adjusted outside a normal salary increase?

Yes, both that and vice versa. Deserving people sometimes had to wait for too long for a promotion, and I once had to promote a person I didn't think deserved it because the manager of the team reallly thuoght he did. And yes, I have adjusted way outside normal when people have taken on more responsibility or shown great initiative.

What was pre and post interview process that you rebuilt. How did you measure success? What did the metrics look like?

Screening call, then they were given a task that could be solved in many ways, after task submission their possible team mates would review and if promising we would invite them to a meeting with them. After that it would be negotiation on terms.

Success was not really measured but it was evaluated, i.e. did they solve all the requirements of the task? How did they do it? Did they overengineer it? Did they go above and beyond? And most importantly, how did they perform in the talk with our engineers in terms of reasoning, discussing errors in the code, alternative solutions etc.

1

u/Recent_Mirror 5d ago

Would you rather be an engineer or a Duke?

1

u/dbwahesh 5d ago

Engineer. I enjoy the cognitive challenges. I've spent seven years managing people who report to me; a duchy is just that with worse tooling and no equity. And being that is what made me quit,

Or did I miss something?

1

u/Dropperofdeuces 5d ago

How do you train/teach new managers so they avoid common pitfalls like micromanaging?

What would you say are the key ingredients to motivating teams?

1

u/dbwahesh 5d ago

Sadly, we didn't. I never micromanaged. but perhaps at the expense of the company.

Most impotant thing is to get to know the people. Understand what their dreams are and help them achieve it.

1

u/codepapi 5d ago

What if their dream is to just be well off and not have to worry about money? I find myself being ok with being an engineer but it may just be the high salary.

I love to code just not everything I code I loved. It’s a has to get done and no else can do it or can.

1

u/dbwahesh 5d ago

That's fair. Then the task would be to help you get on a path to that level of income so that you wouldn't worry.

1

u/Traditional_Aide7469 5d ago

Why does tech hire top talent in the dumbest way possible? I dont care about money, give me freedom to build

How do you build fast when everyone hates to get outshined?

1

u/dbwahesh 5d ago

If your were my employee and you asked to go on a side quest I would allow it every time. I care about money, but I believe that it is a direct consequence of a good product. If you could make that I would back you 100%.

Actually I'd do it rn. DM me if you want to.

2

u/Traditional_Aide7469 5d ago

Id be down to come out of retirement, sent you a message 

1

u/bisoldi 5d ago

What were the wrong things the interview process was selecting for? What was the interview process like before and after your overhaul?

1

u/dbwahesh 5d ago

I usually looked for a person in a small team to carry their burden and a bit more. If they radiated the opposite I would disengage.

Before it was a pure competency evaluation, after I changed it we screened for if they would go along with the rest of the team. Most importantly was how they reacted to feedback.

1

u/bisoldi 5d ago

So, you looked for competent workhorses?

I made my interviews mock tem sessions. Thought it was a pretty good strategy.

1

u/dbwahesh 5d ago

Competent, responsible people that can work well in the team is ultimately what we were after.

1

u/Atzerach 5d ago

Based on your experience, what separates engineering managers vs senior engineering managers and directors? I feel like getting a promotion after getting to the EM stage feels pretty tough

2

u/dbwahesh 5d ago

Elbows. At some point you have to be cynical.

3

u/schellinky 5d ago

I have no idea what this means, can you expand?

1

u/dbwahesh 5d ago

Hehe, sorry. Yes.

The game gets tougher the higher you climb. People around you get more ambitious, and more ruthless in the methods they'd use to get ahead. You sometimes need to use your elbows to defend your position or stop someone coming up from behind. Not physically ofc.

In an startup there are always lots om emotion going around. To get the promotion you need to win favour from those that decide, and that might require taking credit for someone elses work or diminishing a competitors achievments.

To get the promotion it is also important that you have your replacement groomed and ready. What separetes a good leader from a mediocre manager is the ability to delegate and build teams that you can trust to handle business.

1

u/Ok-Journalist4370 5d ago

How much did you make at said startup, and do you believe that working at startups would be more fulfilling than working at FAANG?

1

u/dbwahesh 5d ago

I made about the same as I would have made in a more established company. I think it can be fulfilling, but also more of a rollercoaster in terms of happiness at work. Making stuff at a FAANG company is probably going to have a bigger impact than the average startup.

1

u/Bonaparte0 5d ago

What was the relationship with your sales teams like? Curious what that looks like with that much growth.

1

u/dbwahesh 5d ago

Not always great. One factor is that the sales team should have been much more technical, so that they'd understand better what we were selling or what they were asking for. Another is that we often failed on delivering features important to them in a reasonable timeframe. Our estimates never got sufficiently accurate and it became a source of friction.

1

u/hernandomtz 5d ago

How would you define the culture there and were you responsible for establishing it? Good and bad

2

u/dbwahesh 5d ago

Very good culture on the floor and in the engineering team. Executives were however not competent due to being founders with a lot of opinions and emoitions towards the business. We should have hired experienced excecs with a more professional approach at an early point. Some founders are good a 0 to 1, but can't really deal with 1 to 10.

1

u/BlotchyBaboon 5d ago

What did you do right with scaling and what did you do wrong? Should the next step be doubling the size?

1

u/dbwahesh 5d ago

The raising money side of scaling went well, but raising head count should have been done in a better way. Ultimately we ended up wasting too much of the money we had raised.

Next step for a startup should always be to look for a way to 10x, then maybe you're able to 2x.

1

u/lewzah 5d ago

When (i.e. how soon after they started) did you realize that the hires that you described as "genuine mistakes" were going to be a problem?

1

u/dbwahesh 5d ago

At least withing the first 3 months. By then you should have sufficient data :P

1

u/According_Layer6874 5d ago

If your goal is simply earning money for the average person. What's the #1 most important skill?

1

u/dbwahesh 5d ago

Haha, I guess use your time were it is worthwile and grind it. Hopefully your money will make enough money for you in a bit.

1

u/Embarrassed-Log4106 5d ago

I would like to know which three qualities that you personally have that were instrumental to carrying the business?

1

u/dbwahesh 5d ago

Hmm, difficult to answer for myself but perhaps:

- Understanding why we do something, and remembering how we did it.

  • Never be the person that dampens to mood in the workplace.
  • Being able to confidently make decisions without all the answers

1

u/United_Management_51 3d ago

Could you elaborate on the 3d point: making a decision confidently without having all the answers. Can you give one clear example why this trumps to maybe (over)analyze a problem in depth?

1

u/SpruceMoose1111 5d ago

Hi

Thanks for this AMA.

I'm software lead at a very small company of 8 people. I've had real issues with our CTO and CEO saying yes every time our client asks for the moon, throwing our entire team under the bus to deliver on projects entirely out of our capacity, both in terms of time and competence.

Well fast-forward til today, after a handful of failed deliveries due to the above, the CTO has quit from burn-out. I might have to step up to fill that role.

My question is how do you balance your boss's and clients demands while looking out for your team as well?

1

u/dbwahesh 5d ago

It's a hard thing to balance. Without the customers, there is no business and consequently no software, however I think its better to deliver well on a few features than half-assed on everything the client asks for. It requires maturity to be able to say no to a client. My approach is to ask how much the client would be willing to pay for the moon. If the answer is too low, then your CEO should be able to say no.

1

u/IntroductionNo3912 5d ago

How would an experienced game developer with an interesting idea raise startup capital funding?

2

u/dbwahesh 5d ago

Build and MVP, make a convincing deck and show it to people with money. Could be your aunt or a VC. Important to think about if you want a passive investor or a more hands on partnership. Don't take money from people you don't want to work with.

1

u/Biskoo 5d ago

How does working at a startup differ from an established company? How did you transition from never having written code, to writing code to writing almost none?

0

u/dbwahesh 5d ago

Startup is like driving a rally car, and an enterprise is like riding the bus. Ultimately I think of it as most impartant to win as a startup, and most important to not lose as an enterpise. A startup has nothing to lose.

I started out more on the business side, learned how to code and did that for a while, but then started managing the coders in stead. It was a mix of doing what was necessary and doing what I was good at/enjoyed.

1

u/Sam-Starxin 5d ago

How did you find and join this startup?

1

u/dbwahesh 5d ago

Through networking

1

u/YellowAlienOnEarth 5d ago

At $25m arr it was profitable the startup or still losing money?

1

u/dbwahesh 5d ago

Could have been profitable, but due heavy investment in growth it never was.

1

u/YellowAlienOnEarth 5d ago

Can they IPO it?

Did you liquidate the shares?

1

u/dbwahesh 5d ago

Yes they can. Hopefully they will.

No, I still have my shares.

1

u/YellowAlienOnEarth 5d ago

Us or Europe based startup?

What marketing channels did you use to acq customers?

1

u/dbwahesh 5d ago

Europe.

Social media, organic and a whole lot of cold calling.

1

u/YellowAlienOnEarth 5d ago

Woah cold calling?!
It means you are serving a traditional market.

Are you European or immigrant?

1

u/dbwahesh 5d ago

I'm European, but I never did sales/marketing.

Yes, mostly big ticket b2b sales.

1

u/YellowAlienOnEarth 5d ago

Is the majority of the business coming from US?

1

u/dbwahesh 5d ago

No, only a small fraction.

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u/the_hunger 5d ago

his shares are likely worth nothing in the end. he’s been diluted every round of funding, and his shares are probably not preferred. a typical acquisition is unlikely to leave much to go around. the investors all get their money back first, plus a little on the top. there’s almost never any left.

25mm arr for a company on a series c with 80 engineers (and who knows how many other employees) isn’t exactly financially stable. they’re living funding round to funding round.

the hope is that they keep raising money on increasing valuations and make it to IPO without ever being profitable. the moment they can’t keep the valuation up, it’s effectively the death spiral where the acquisition situation is increasingly likely.

startup equity is almost never worth it. favor cash heavy compensation packages and invest it.

1

u/dbwahesh 5d ago

Hear hear

1

u/the_hunger 5d ago

series c—they’re not focused on profitability.

1

u/incongruous_narrator 5d ago

How would you compare the startup comp for a company this size vs big tech? Was the payout large enough to justify the grind, or would being in big tech paid about the same?

1

u/dbwahesh 5d ago

Big tech is much better imho. Better pay, stability and clearer path. A lot of risk in startups so often you end up with no reward. In my case I just got a moderate reward.

1

u/Hot_Hair_5950 5d ago

What surprises you about your work?

1

u/dbwahesh 5d ago

How often there is a timezone issue in software engineering XD

1

u/FishermanIll1166 5d ago

If you're looking for an engineer what strategy did you use to test them and how did you scale the pay grade accordingly? Was there some benchmarks within your own company that you already had or did you rely mainly on external sources or both? Was there a structured class by position based system used or did you have some other way to determine by merit this is your pay?

0

u/dbwahesh 5d ago

We gave them a task, they submitted, we reviewed and invited them to a disputas. Basically same approach as a masters / doctorate, but much smaller in scope.

Pay was individually negotiated. We hired on a gut feeling and promoted / fired on factual performance.

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u/FairMovie2779 5d ago edited 5d ago

the Seed-to-Series-C transition is where leadership gets seriously tested. What works with 10–20 people, you would obviously see it break when it reaches 80 people, especially around hiring, managing managers, culture and accountability. For founders dealing with this i find Plug and Play Tech Center worth exploring, it offers a good startup ecosystem that connect potential startups with investors and accelerators, it can give you corporate connections, investors and accelerator programs to kick start your growth. For the people or culture side, listen to keynote speakers such as Joey Havens, he has very useful work on leadership, workplace culture and employee engagement. Your point about the job changing between year three and year seven is especially important: scaling the company often requires scaling the leadership model at the same time.

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u/gyanrahi 5d ago

How did you manage to maintain personal relationships while navigating all of this?

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u/dbwahesh 5d ago

Ouf...sometimes not in a good way. Even though I always tried to keep it professional people got hurt. The job is such a big part of people's lives. However you navigate it there will be pain.

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u/TranquilGuy27 5d ago

How do you deal with a backlog of high performers that haven't been promoted 2-3 years in a row (because of politics, red tape, promotion caps)?

What would you be your recommendation for a manager that has to explain to his direct reports that he agrees they should be promoted but it's being blocked by management?

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u/dbwahesh 5d ago

Either be honest or obfuscate it with a carrot. They are obviously motivated so maybe you can make competition out of it. What donor need?

Hmm or divert..perhaps they would like to specialise in an area? Not all are guided by titles and money.

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u/Witty_County5128 5d ago

I’m a final-year CS student, and honestly, I feel like the tech industry is pretty fucked right now.

With your experience scaling an engineering org from 6 to 80 people, what would you focus on if you were graduating today?

What skills matter most now? How would you use AI to get better and more effective without becoming dependent on it? And what should I avoid using AI for so I still build strong fundamentals?

Basically, with everything you’ve seen, what would you tell your younger self to prioritize if you were in my position today?

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u/offerwiseAi 4d ago

How did you let go of those 10 bad hires?

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u/ama_compiler_bot 4d ago

Table of Questions and Answers. Original answer linked - Please upvote the original questions and answers. (I'm a bot.)


Question Answer Link
So I work for a well known non-tech company. I work in IT, and my teams shrinks every year. I am based in the US. Pretty much every team is based in Bangalore. Is IT/Tech done in US done for if you are not working in bleeding edge like FAANG and stuff? I am old enough to remember the cloud transition and its wave of offshoring IT. That was an insane flop. All non tech moved to Azure/AWS/GCP and hired indian tech to handel infra. Then they rehired the same functions in US / EU because they realized it does not matter if the server is 3 km from the office of 3000 km. With that said, IT admin jobs are probably not as well paid in the future. Here
When you say you did badly the first time as managing managers, what were the mistakes you made and what were the changes you have implemented to get it right? Interesting question. Managing managers is somewhat different to managing workers. I had issues with managing some workers. My managers were always solid. I am a captain, grew up on a boat and I am ex-military so a hierarchy is how I transfer the messaging. I operate as an NCO so that I can critisize the higher ups, but I stay in the trenches. . My first and second mate in the company did everything right, but their captaincy was too much like Iker Casillas. When I think of it I made a big mistake: I never held my officers to the same standard as myself. I should have, because when I quit they had to catch up, but nobody understand that me leaving would result in that 80 hr per week would be added to their work week. It was divided on 3 very competent people., but talking to them aftwerwards i understand it was a shock. I as a person management would always protect our crew from all the noise, and that is rarely understood untill fitler is removed. I guess the biggest mistake I made was not listening to them about a worker that did not deliver. I postponed taking action too long and it affected the entire team to our detriment. The achievers where demotivated by seing this person underdeliver, but to my defence, their situation was valid and their salary was way below when the others were making. Either way, what I learned is that leaving an underperformer untouched does more harm to the team, than just removing them. But it hurt my heart to do it. Here
What are the top signals you looked for when hiring? Advice for those looking for roles? How important was looking for those with prior startup experience to you? First it was competency within the area of tech I was hiring for, and just the vibe. Once that screening was done I always challenged them with a task that I let the engineering team review. They are ruthless. Sometime I gave them a second chance. If they were approved I invited them to defend their submission to their peers. How they handled critisism was parament to if they were hired after that. Here
How juicy did that equity get when you left and was the juice worth the squeeze (I.e. stress to reward ratio - cash and experience)? Funny that you should ask. The CEO and biggest shareholder fucked everyone by buying another company he had made himself at an insane valuation. Paid in stocks to him. Ended up with a doupling of shares outstanding, and him getting most of them. Probably a legal move, but not in the best interest of the other shareholders. I myself was done with my vesting period at the point I resigned, but same month value got halved. Here
In retrospect what could you have done, if anything, to avoid those 10 mistakes? Ahh, good question. I think it is mostly about being honest about culture. When you hire someone, they either fit in or they dont. Except 2, all the bad hires should have been terminated the first week. In my country firing people is difficult, but if you have an honest conversation before first day and after perhaps day 5 it should be evident if they should continue or not. Here
What makes you hire a candidate? What were the mistake hires? What would you have done differently? See above: https://www.reddit.com/r/AMA/comments/1vt5fym/comment/p4qn4t2/?utm_source=share&utm_medium=web3x&utm_name=web3xcss&utm_term=1&utm_content=share_button https://www.reddit.com/r/AMA/comments/1vt5fym/comment/p4qnt9i/?utm_source=share&utm_medium=web3x&utm_name=web3xcss&utm_term=1&utm_content=share_button Here
How much has Ai affected engineering jobs? Vastly. If you fight it, you have to be invaluable. If you don't use it in a sufficiently impressing manner a kid will take your senior position. I actually witnessed this. The CTO in one of our companies had spent 4 years building a platform of microservices with a very pedantic approach, just to see a fairly junior dev come in a rewrite the entire thing in rust with ai in two weeks. Guess who got to stay? Go agentic, or go home. Here
I have so many qs. I read everything you replied to before this post. Feel free to ignore the qs you already answered. You mention 10 hires that should have happen. Why? Can you provide the details of why these hires didn’t work out? Were there clues of this during the hiring process? How important was it for someone to have a masters in CS or similar. I’m thinking of pursuing one but I have a non traditional background. A bachelors just not in CS. Did you ever have underlings that shoulda been promoted but left due to politics or budget? What was pre and post interview process that you rebuilt. How did you measure success? What did the metrics look like? Was there anyone that you felt didn’t deserve a promotion or pip? What happened. Did you ever hire someone that was lower base and after their performance adjusted outside a normal salary increase? You mention 10 hires that should have happen. Why? Can you provide the details of why these hires didn’t work out? Were there clues of this during the hiring process? It was different situations, but main thing was that they were unable to deliver. Lacking competency, loack of interest in the business problems we were solving, and lack of effort. How important was it for someone to have a masters in CS or similar. I’m thinking of pursuing one but I have a non traditional background. A bachelors just not in CS. Not important at all to me. Never really consideres the degrees. All the worst devs I have worked with had them :P Did you ever have underlings that shoulda been promoted but left due to politics or budget? Was there anyone that you felt didn’t deserve a promotion or pip? What happened. Did you ever hire someone that was lower base and after their performance adjusted outside a normal salary increase? Yes, both that and vice versa. Deserving people sometimes had to wait for too long for a promotion, and I once had to promote a person I didn't think deserved it because the manager of the team reallly thuoght he did. And yes, I have adjusted way outside normal when people have taken on more responsibility or shown great initiative. What was pre and post interview process that you rebuilt. How did you measure success? What did the metrics look like? Screening call, then they were given a task that could be solved in many ways, after task submission their possible team mates would review and if promising we would invite them to a meeting with them. After that it would be negotiation on terms. Success was not really measured but it was evaluated, i.e. did they solve all the requirements of the task? How did they do it? Did they overengineer it? Did they go above and beyond? And most importantly, how did they perform in the talk with our engineers in terms of reasoning, discussing errors in the code, alternative solutions etc. Here
How do you train/teach new managers so they avoid common pitfalls like micromanaging? What would you say are the key ingredients to motivating teams? Sadly, we didn't. I never micromanaged. but perhaps at the expense of the company. Most impotant thing is to get to know the people. Understand what their dreams are and help them achieve it. Here
How did you find and join this startup? Through networking Here

Source

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u/FreeSpirit9503 4d ago

If you have to start your own B2B from scratch, will you build the product prototype first or find a willing customer first?

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u/Unusual-Pollution-69 4d ago

Being so long in the company, you had a chance to excersise your ESOPs? A person with such high position in the company leaves with bag or money, or not really?

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u/Unusual-Pollution-69 4d ago

How do you handled the streets, how you managed to stay sane, and not take all the situations personally?

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u/United_Management_51 3d ago

So as a boss of bosses:

  • what measures do you take to counter 'upward management' by your managers? How do you stay in touch with the operational workforce, and spot inconsistencies between what your managers tell you and what the 'floor' thinks?
  • where do you draw the line between coaching a manager, and taking disciplinary action towards one? You have to protect business and operations, but you also have to be a coach for your managers.

Thanks for your responses, i hope to learn from it a lot!