My last company is stonewalling on how to exercise shares

The answer to the question 'Is there anything I can do?' in our society is almost always 'You can get a specialized lawyer'

Sometimes just writing an email that is obviously written by/with legal counsel speeds things up immensely, in my experience.

I'm not qualified to give legal advice, but my life advice is: get legal advice if you can afford it.

Depending on how large the company is, how it is structured, and how long they have been around, it might be the first time they've had to facilitate this exact transaction. It is possible that they are dealing with their lawyers to guide them on how to proceed. My mind wouldn't go straight to foul play.

My advice here would be to collect all of the documentation you can and make the clearest, most complete communication of your intention that you can through a channel that can be stored for later (email or registered mail including a dated letter with an indication that there is a copy).

Give the benefit of the doubt: "I realize that you are busy and may be trying to figure out how to proceed."

But super clear about concern, intention, and desired outcome: "I would like to exercise my option holdings at this time. I want to make sure that we are able to conduct this transaction in advance of the XYZ timeline detailed in the option plan. If, for whatever reason, it is easier for me to make this request of some other individual, group, or firm, please do let me know.

If you know the corporate law firm that represents the company, you can also reach out to them directly or indicate to management that you are going to reach out to them (not in a threatening way, but in a I'm-looking-for-a-response-and-am-not-going-away way). The law firm may actually be the option plan administrator, and they are duty-bound to administer it per contract.

Good luck!

Send them a check for the total exercise price along with a letter (maybe a plus to have it drafted by a lawyer) and send it by certified mail.

If you've got shares, you can either hold them or find a private buyer. Often a private company will have first-right-of-refusal but would have to match a private buyer's price.

Since you're using the words exercise and vested, maybe you have vested options in which case the policy (by law depending on jurisdiction) should tell you how long you have to buy your shares, how the price is determined and when the company has to respond with the strike price. IANAL but giving you 90 days to exercise your options and waiting 91 days to tell you how seems illegal in several ways.

Your original stock option agreement should have a form that you can use to exercise the options. Fill it, attach a check for the exact amount and send it by certified mail. It doesn’t need to be more complicated than that.

Try calling them on the phone.

I'd definitely hang on to those, as they will massively increase in value if the restrooms run out of toilet paper.

Is it not your own responsibility to retain professional assistance to manage any transactions you may wish to perform?

Couple of important points I haven't seen mentioned yet.

1 - You should already have an option exercise form that you can fill out to actually exercise these options / notify the company you want to do so. It is important that you fill this out and have it in writing, email/certified mail/whatever, that you sent this in with a request to exercise because of 2.

2 - Depending on your employment agreement and your role, you should find out exactly what your Post-Termination Exercise Window is. This is the time period in which you have, after a certain condition, the ability to exercise your options. If you do not exercise them within this period, in most cases, the options will revert back to the company and you will not have the ability to exercise them in the future. This can often be as short as 30-90 days. While I would try to assume positive intent, you need to make sure they are not trying to wind the clock down against you.

3 - You should also be aware of the cost to exercise the options and the number of options that you have vested at the time you leave. In your grant, there will typically be several components, most importantly the strike price, the number of options and the vesting schedule (typically 4 years with a 1 year cliff). While there is much to work through with your lawyer, in general, Strike Price ($1.00) * # Options Vested (5,000/10,000) = Cost to Exercise ($5,000)

4 - Keep in mind that once exercised, if the shares turn out worthless, you can't get the funds back. The shares can end up worthless for any number of reasons including Investor Preferences, Debt Overhang, or a sale price that is too low. Overall, do your own risk/reward calculation here to make sure its worth the price of admission.

5 - I'd echo the points here in that they may never have had an employee exercise their options previously. Believe it or not, most employees do not exercise when they leave a company, and you may have been the first to do so here.

6 - Finally, document all of this thoroughly. If for whatever reason they are attempting to run out the clock on your Post-Termination Exercise Window, ensuring that you have documented you WANT to exercise them and the company didn't execute on your desire is critical in eventually getting the options.

(IANAL and you should find counsel to work through the specifics with you, this is not legal advice and there are unintended tax consequences that may occur if you don't consult a tax professional - Options are complicated!)

Did you check your original option grant? You would typically have a copy of the exercise form attached. It might look something like this.

https://slack-files.com/T02FQ9S94-F033ZGVFG6S-dc3480af16

Maybe give it some more time…? If they still refuse to help you I would get in touch with a lawyer.

I'm having similar experience at current company. In my case I'm still an employee and haven't said anything about leaving. Gone back and forth between 'red flag' and 'normal startup disfunction'.