Navigating Startup Growing Pains Situation

>>On the otherhand, I know I would resent the technical cofounder receiving an enormous financial benefit from developing a non-viable disaster from which the company needs to be rescued.

If the technical cofounder created a working prototype that allowed the company to achieve certain milestones (e.g. paying customers, seed funding) then I'm not sure why you'd be resentful because it seems the (initial) job was accomplished.

You rightly point out that you bring a valuable contribution to the table, but it seems you might (possibly) be underestimating how capable and determined the founders (and their investor network) will be able to source somebody else to rearchitect the platform.

If you're one of the few luminaries in your niche, then feel free to start negotiating for a large compensation package that includes serious equity or favourable provisions. If on the other hand you feel that there could be others that could rearchitect on a "good enough" basis at a (potentially) lower compensation price point, then perhaps you might want to lower your expectations walking into the initial negotiation.

Either way, it intuitively feels that your expected negative emotional resentment is not the right frame to start evaluating the possibilities around this opportunity.

I have been in similar shoes, and had a huge impact as a founding engineer (#2 employee) at a startup (now unicorn). I wouldn’t say I had tremendous niche skills, it’s more that I took so much direct ownership and accountability of so many problems that I was able to have outsized impact for the first few years until the company became too large for me to keep track of all of it (many years later). The founder knew my personality traits (we worked closely before) and chased me very hard in the hiring process.

Many new employees and customers would ask me, after seeing me operate: “Why aren’t you the CTO and the founder is, since you are the de-facto technical authority here of every system?”.

I had a successful career at that company but I never really brushed off the exact resentment you talk about, so if I were to do it again I don’t know if I would. It was a very hard emotion to deal with.

You build something great one day or enable a massive new customer deal, get a rush of endorphins because you single-handedly made it happen via heroic efforts, then you remember your financial outcome will be a tiny fraction of the founder’s. My equity will be valued at best ~$10M (or more likely the ~$2M I already cashed out and the rest $0, we’ll see if they survive this downturn), whereas the founder will easily take $1B+ from this (and has already cashed out $xyzM).

These days I’m generally “happier” at FAANG being a good team player and just helping everyone around without a “grandiose” mentality, I am at peace with being a small cog in a large machine. I don’t think I will ever do a startup as a non-founder again, I don’t want that feeling to surface ever again.

From a cursory read, it seems like you may be in for a similar path with similar inner demons.

The most challenging part about any startup is NOT the technology it's building but finding product market fit.

The company did all the work to discover that, and what's stopping them from finding someone else to build it? Why does it have to be you?

> How do I negotiate a situation where I can receive the value of what I provide?

This is a good question. But before you find the answer, you have to drop the resentment. Other commenters have covered why, but if you cannot get past that, this role is not for you.

You also need to accept two important truths:

1) The success of a business is about far more than the elegance of its tech stack.

2) Your ability to re-architect a platform is not unique.

Focus on your own correlated truths:

1) The operational optimization of a business is correlated to the elegance of its tech stack.

2) Your background will make it an easier road to walk to re-architect vs. people without your background.

In short, come in showing them that you offer value above others and can help them succeed. But do not walk in as a prima donna acting like you are their one and only savior. Ask for compensation that makes the work worth it to you, but don't begrudge them their own success.

You are potentially being hired to solve a different problem than the founder at a significantly lower personal and professional risk to do so. There's nothing to be resentful of.

But I say potentially because if they find this you will probably be rejected as an applicant. This is a major red flag to any hiring manager.

With your expertise and the fact that they're so early, you should be able to build a competing business with your superior product right?

Then you can keep all the rewards (and find out all they had to do to be in the position to be able to hire you).

Sounds like a win-win, you should be talking to startup accelerators not startups hiring.

Start your own company.