BayAreaSmayArea

I've got a good dilemma going. Background: I was first employee turned CTO at a startup that exited. We did ok. Not great, but not bad either. I left the acquirer after a year or so, making sure my team and our tech was taken care of and since then I've done some contract work while I looked for something permanent. COVID extended the contract work a bit but happily I'm now looking at two competing offers.

One is from a FAAMNG type company for a high level IC developer position. The total comp is good, and I can probably negotiate it up a little higher.

Two is from a Fortune 50 company that is trying to get part of their tech in order. Its for a 2nd level engineering manager supporting several teams and few dozen people. The total comp is in the same ballpark as the FAAMNG-type, but its less, and the RSU component is unlikely to have as much upside since its not directly tech.

I still have the chops to be an IC, and have cranked out a lot of good code while doing contract work, but I'm wary of taking on a full-time IC role and having to break the management barrier again (which feels like it could be especially difficult in our new remote-everything world).

"leadership" roles are definitely where I want to be going forward, and it is something I think I'm fairly good at. But I've found in my current search that FAAMNG-types don't seem to care much for startup experience in management roles. Maybe heading up larger teams at Fortune 50's look a little better and can demand better comp'd positions in the future because of it? It seems like promoted from IC to a 2nd level manager anywhere is a big challenge.

Have any of you been in a similar situation and care to share your thought process?

tldr: I realize the answer to this is "talk to a lawyer" but I'm curious of what the process looks like.

The long story is that I formed a corp using Stripe Atlas earlier in 2018. We were making plans and had done some prototyping, and it seems like a good step to solidify things. Following that my cofounder has had a lot of life changes going on, some negative some positive the are going to require them to move aboard. We realize that this isn't a great recipe for building a successful company so we're figuring out proper steps to close it down and maybe do something else in the future if we're ever living in the same city again.

We're on good terms so there is no current conflict and I don't anticipate any. We didn't issue stock, and didn't assign any of our work to the corp. But I'm unsure of what the process looks like to roll this down so that we don't have an unexpected tax bill or something like it come up later.

Specifically a software offering in the B2C space, but something more general works too. What books/articles do you recommend for a product and technology background person to get their heads around to-to-market?

How are non-solicitation agreements typically viewed for colleague leaving to start a business together?

For instance an engineer and product manager decide to leave a company that they’re both working for to create a startup in a non-competing space. Are they opening themselves up to liability for “soliciting” each other to leave their current job?

Disclaimer: not looking for legal advice, and if I actually needed it I would find an employment lawyer. I’m merely curious and my searches are coming up empty and tend to only focus on the customers/sales aspect on non-solicitation.

This weekend I spent some time going through Tren Griffin's new collection of essays "A Dozen Lessons for Entrepreneurs." There is some good advice and great content. I can't help but notice a big gap in the talking points of these VCs about partnering with founders and providing a network of resources vs my own experience.

At my last startup we had investments from some very big names that you'd all recognize. I think that they collectively provided one great enterprise lead and hosted a couple of meetings around that lead. The founders/founding team did key hiring with our own network and cold reach out.

I'm wondering, was our experience out of the ordinary. I assumed that the network effect of investors was largely about networking to other investors and the rest was just flowery language. But now I'm wondering if there is more to it and we didn't use or weren't offered all of what our investors had to give.

Have you gotten anything more from VC firms than a cash for equity transaction?

Background:

I joined on as one of the early employees at a startup a couple years ago. I liked the idea, had previously worked with one of the founders and took the lead developer role. Things have gone well, the development team has expanded, hiring a few really talented devs and many other quality contributors and along the way a VP of Engineering who is far better at the people-oriented parts of running and building a dev team.

As those people have come up to speed and the product solidified I've handled off more and more and now find myself mostly stepping back from development. I'm still in discussions about technical plans, but now I'm also spending time in conversations with PMs about new products/directions, timelines and planning of feature rollouts, and being brought into larger sales deals/partnerships as a bridge to the technology side of the house, speaking on behalf of the company at various events, serving as brand expert, and mentoring up younger devs.

Part of me feels like I've been put out to pasture, but the larger part seems that I've fallen into quite a great opportunity for growth and a perfect opportunity to train up for a CTO/technical founder type position in the future, and maybe just a bit of "reward" for being an early employee that went all in with the founders. I'm doing less, sleeping more and easier, cognitive load has been nicely reduced and creativity/ideas are flowing as well as ever.

Things are good, but I can't help but feel a little strange for not being more directly involved with development.

Foreground:

For those of you who have made a similar transition, how did you handle it? Did you do anything to scratch the itch or did it just go away over time? Do you worry about losing anything? How did you adjust to a role with much less direct "proof of work" but not in a management role?

I'm hearing more and more that VCs are asking for the removal of single trigger clauses for founders and key employees.

Have you every been asked to give it up? What did you get in return and how do you feel about your decision in retrospect?

I don't have enough insight into the larger startup world, but had this discussion with some coworkers and was curious of the HN opinion.

Are there any startups using Java, not the JVM, today? Say any in the last year or two of YC classes?

If so, and you're at one of the startups, do you feel it has affected your ability to bring in development talent for the better or worse?

Good evening all,

I'm currently doing the first engineer deal at a startup privy to a lot of things but very clearly not a founder and not in the financial conversations. Everything is going well we've got term sheet(s) in hand and it looks like we'll be taking on some investment in the next few months.

One thing that I've heard and don't really understand is that some conversations are leaning towards vesting being reset. Understandable for VCs to ask it of founders, but can/does this tend to affect employees, and does it require consent for the employees that have already signed grant/option agreements?

I've never been a huge fan of the 1 year cliff for early employees, myself being one. I've been looking over some terms of a new agreement, and it seemed to be that it would make sense for there to be a vesting trigger clause based around receiving investment, perhaps over a given criteria to move things a little more towards "fair" from the employees point of view.

Typical equity agreements have the 1 year cliff for 25% of the employees shares to be vested followed by 1/36 each month or 1/12 each quarter. It seems to me that the 1 year cliff doesn't make much sense for the earliest employees, if they've done enough after 6 months that the company takes in a round of funding (1M or more) that they should immediately vest to that point and start the standard vesting clock at that point.

Has anyone ever seen a clause like this in their agreements, or insisted on one? Am I far off base for thinking this shouldn't be unheard of?

I've been approached with an opportunity to work at a new startup. I've known the founders for several years, working with them at one point or another. They understand both the business and technology side and have had several successful exits.

They're self funding, offering competitive, but reduced from my current, salary of 100k and 2% grant. My risk is essentially nil with how good the job market is, and my upside will be nice if we're successful. The position is first employee and lead architect. It seems like a favorable offer and it seems like the numbers line up fairly well for what I see for post series A startups.

Theres always talk here about not working yourself to death for minimal equity and not getting blinded by it, but being new to the startup side of things I don't really have a clue about what "significant equity" means and the self funded nature of the business makes things more confusing. I don't expect to get rich from it, but I think we've got a good plan and history of executing well so we've got a good shot at turning time into a good payoff.

So, HN, at what point in the ownership percentage do you go "all in" on? 2%, 5%, 10%, 25+?