Take leadership opportunity and fix current mid-size company or join early stage start up?

Posted by m4sterbuild3r@reddit | ExperiencedDevs | View on Reddit | 13 comments

Got opportunity to lead the entire engineering function in current company. Will be reporting to the CEO and I’ve got a lot of respect and influence.

It’s a scale up B2C fintech (50k customers, 50 employees) - have PMF, but tech is still lacking a little.

My dilemma is many bad choices were made by my predecessors, so there’s a good chunk of tech and ppl debt. But I do now have ability to fire the bad engineers and replace without question.

CEO is interested in pursuing interesting tech too - but realistically probs a little while longer of rewrites/stabilisation and fixing team. Plus side I have hired my friend who’s a great engineer and willing to help me fix this.

Money is good, room for growth.

BUT I can’t decide if I’m wasting my time given a lot if it will be getting the basics right and I have opportunity to move to a much smaller applied AI start up with a really smart team, engineering founders and good tech already (clearly won’t make the same mistakes my current company made to begin with).

I can’t decide what’s better for my growth - take leadership opp in current company and improve the eng team/product then pursue some interesting tech OR just jump to this v early stage start up that clearly are good engineers but won’t have as much influence/leadership - although I imagine i’ll learn a lot from the team.

I’m still quite young (late 20’s)

[-]

llanginger@reddit

I guess I have a couple of thoughts;

Late 20s seems very young to have a CEO telling you you’ll be in line for CTO. Maybe you’re totally ready (as much as anyone could be) and maybe this works out great. The simple fact of my experience (totally anecdotal!) is that the majority of young engineers who get promoted too quickly have landed themselves in a position where they feel out of their depth, and haven’t had enough high level experience to support them as their imposter syndrome flares, and end up making consequential decisions that don’t go great.

If you do go this route (which I’m NOT suggesting you shouldn’t), I would strongly recommend that you get your company to fund some executive coaching. I would also suggest investing in your own therapy / professional coaching as a way of preemptively squaring up to the new pressure you WILL be under.

Imo you’re far more likely to get an opportunity to join an early stage startup again than you are to be on a fast track to CTO, and in your shoes I would take that option!

[-]

PragmaticBoredom@reddit

I’ve interviewed a surprisingly large number of young people who had CTO titles on their resumes. There’s a lot of truth to this comment.

It’s very important to understand that the “CTO” title is relative to the size of the company, size of the engineering team, and scale of the technology product. Many of the ex-CTOs I interviewed had responsibilities on the level of a Director, Engineering Manager, or even Tech Lead or Team Lead in their jobs. A lot of the candidates were honest about it, but some of them had resistance to the idea of going back to not being in charge of all of the tech decisions in their next job.

Being the CTO of a rapidly growing fintech with successful exit could set someone on a great career trajectory. The difficult part about this post is that I don’t see any of the signs of that they might be on that course. That could all change, but it’s a hard turnaround for the company and a turnaround probably is not going to be lead by the tech stack but the business side.

The difficult signs in the post are that the previous CTO was fired, they have had no CTO at all, and the tech stack does not appear to be in good condition. All of this adds up to suggest that tech is both not critically important to the company and they don’t value it much in hiring and organization structure.

Which brings me to the biggest risk I see: That the promise of a CTO title is being dangled as a carrot to get someone to work disproportionately hard. It’s a pattern I’ve seen a lot in the ex-CTOs of small startups that I’ve interviewed: They worked very hard to make the tech work for the promise of a CTO career, but the company was using the title to extract more commitment out of someone who was basically an EM or even tech lead who would otherwise bail on the company if not for the title.

I could be misreading it, but that’s the concern I’d be watching out for. Executive coaching could be helpful if the position turns into a real executive role, but in many situations like this it’s less of an executive role and more of an aspirational title.

HalcyonHaylon1@reddit

Dont go the startup route. Its filled with risk, and politics.

08148694@reddit

A C-suite (which the stay option essentially is) level role is political and managerial in nature

This really boils down to if OP wants to be hands on techy or management

A CTO deep in the weeds of programming isn’t going to be an effective CTO

Both options the op is communicating are fairly high risk, but also agreed.

snoogans235@reddit

Personally, I’d go startup. It’s a risk, but you have 30+ years to gain more experience in leadership roles. Which it sounds like you’ll get at either position. On the flip side, the manager promising to promote you is a huge red flag. If he wants to promote you, then he should hire you into that role. Don’t take a job on a promise made in an interview. Or do, but make sure there’s a clear path to that promise.

PerspectiveLower7266@reddit

So I never trust promises. A promise is a great way of manipulating someone to do work without the pay. Something doesn't pass the smell test with your current company based on what you've said.

vansterdam_city@reddit

I’ve taken the leadership opportunity to drive a large org (150+ engineers). It takes years to develop the organizational trust and depth of understanding to get an opportunity like that. I think you will learn a lot.

Startups are a dime a dozen. If that one doesn’t work out there will surely be another opportunity later. But you probably won’t get such a leadership opportunity again without growing into it somewhere else for a few years.

rayfrankenstein@reddit

Here’s another a simplistic litmus test to find out if your employer is serious.

Don’t fire anyone. Yet.

Instead, ask to upgrade every developers’ work laptop to a maxed-out macbook pro (maybe M4, 128 GB RAM).

Add licenses GitKraken, Cursor, other useful dev tools to request.

Add O’Reilly subscriptions for each dev to request.

See how quickly it’s implemented vs how much hemming and hawing and word salad and accounting mumbo-jumbo is thrown at you.

If they say no, if they’re unwilling to make 100-200k in changes that don’t involve headcount, you may be dealing with systems’ problems that your predecessors weren’t allowed to fix but were scapegoated for not fixing. And in that case you’re walking into a trap.

above_the_weather@reddit

What the fuck? This is crazy advice

just_testing_things@reddit

Get on the leadership track earlier than later.

nickisfractured@reddit

Level up your team, so much more low hanging fruit and the stick to enact change with trust is amazing especially after a few years. Code is good and it’s a good skill but if you can motivate a team, get them to be their best and make them care about what they’re doing everything they touch will be great. Creating a team and raising there bar requires a whole different set of skills but with both your unstoppable

m4sterbuild3r@reddit (OP)

good way to put it man, thanks.