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Other answers are correct in that you should not handle this via HR or your company. First of all, it's not your company's responsibility, and secondly, it didn't even happen on company property (it was on a public lot).

However, I do not agree with the other answers that you should keep your head down and suck up the costs.
Warning: Depending on your culture, if there is little to no worker protection from being fired by a vindictive manager, and you want to guarantee keeping your job, you need to evaluate whether you want to avoid getting unjustly fired at all costs, or whether you'd rather have your repair costs covered by the person who caused the damage. The rest of this answer assumes you want the latter.

Simply address this like you would if you didn't know the person at all. Document the vehicle (take pictures of the dent/green paint/license plate) and go to your police station and ask them to look into it. Isn't that what you'd do if this car was driven by someone who is a complete stranger to you?

Whether they will do so and whether this will change the insurance company's response depends on your case and local culture. This is not something I can conclusively answer. I can imagine this turning out very differently, e.g. stereotypically comparing a metropolis (police are too busy) to a small town (police may have time to look into minor local matters).

Ask her directly and politely.

First of all deal with your anger, your anger is your own problem.

Approach her and explain what happened. Don't accuse, just explain your car was damaged, which day, you don't kow who did it. Say that you noticed the dent in her car that is kinda matching yours and ask her if she thinks she could have accidentally done it without noticing. Make sure this conversation takes place near both cars in the parking so the evidence will be in front of your eyes.

Accept that her dent might be from another incident and someone else might have hit your car. As a matter of fact, once I was in a cinema parking lot and a guy asked me if I bumped into his car because I had a dent in mine, but my dent was from another incident, I was not guilty of this. Maybe it's even YOU who bumped into hers, without noticing because your music was too loud or something.

When you will ask in the parking she will either:

1. She will aknowledge her responsibility. In that case, try to settle this friendly and without involving the police. She might offer that you deal with her insurance company, or she might only offer an apology, which is better than nothing and might give you peace. It's just a dent by the way, so it's only esthetic and it's normal that you be emotional, but you should let it go and accept that your car is not flawless anymore.




2. She will deny damaging your car (truthfully or not). In that case you should believe that she is honest and move on, that is for the best. Show her that you believe her and that you don't resent her, you just wanted to respectfully ask. She will not hate you for asking. A dent is not a big deal anyway.

In all cases don't get into an interpersonal conflict with your boss's boss. And remember, deal with your own emotions, your anger is only for yourself and it's not useful to dump it on someone else.

Just tank the costs of repairs. Unfortunate as it sounds.

Circumstantial evidence isn't strong enough to make an accusation and even if it were, the fact that this happened outside of work premises means that this would be better off discussed in private as opposed to involving HR.

HR have better things to do than worry about employees' cars getting hit in public lots, whether by another employee or not.

On the insurance side, I would inform both my insurance and the police that I suspect the car that hit me is -insert boss's car description and number- and that I saw that car in the same park a few days later, still showing signs of damage that are consistent with the incident I reported. If they decide to take action on this or not is on them, not you. I would also seek legal council in case my insurance or the police refuses to act on provided information.

On the personal side, I would try to email the boss person telling them I was involved in an incident that resulted in damage to my personal property (with detailed description of where and when, and what my car looks like) and I suspect her car was involved based on damage I observed in the parking lot. I would also ask her if she knows anything about it. Do not threaten, do not provide more information than what is required for her to identify your vehicle and time/location of incident, do not require anything else other than asking if she knows anything about this.

Unless you had a witness who saw the collision or CCTV footage of it then there is nothing you can do.

The person who damaged your car did not leave a note and therefore has no intention of owning up to it so if you confront them they will deny it.

Even if you can prove that they did it you'd need to decide whether the cost of repairing the damage is worth more to you than the aftermath of calling out your boss on it.

I'd take this one on the chin and put it down to experience personally, the juice is probably not worth the squeeze.

Let's consider the path you didn't take.

You have no earthly idea who owns the car that hit yours. So you snapped pictures of the car showing the damage and license plate, and took that to the cops, along with info of where the car tends to be parked. The cops decided how hot-n-heavy they wanted to get, and how exactly they wanted to take down this armed felon, if that's what he turned out to be.

Parallel to that, you also took this information to your insurance company, so they could send their adjuster out there and try to catch that car, and/or identify the owner and liase with that car's insurance company. This would have gotten your car fixed, obviously.

You did not choose that path, for reasons which are your own.

The path you did choose

Instead you chose to lay in wait, with an aim toward a confrontation. The problem with such things, is that they can go really sideways in a lot of unexpected ways. You know that, or reasonably should have known that.

And lucky you, it did go sideways in one of the more comical ways it could go, torn right out of a Jennifer Aniston movie about the workplace. Instead of one of the horrible ways it could go.

But as a result, your options are spent. Your actions had the effect of stalking your boss's boss, but not the intent and nothing more has come of this, so it can be dismissed as coincidence. You know the saying about odd misfortune:

Once is happenstance
Twice is coincidence
Three times is enemy action

This person is known to be cowardly, deceptive and manipulative. So if you press the matter further, she can be expected to try to disclaim the garage bump and use the weird garage encounter to twist your claim into an accusation against you.

Even if you now go to the police/insurance, she could claim you intentionally hit her so you could fabricate the claim as part of your stalking.

Have the courage to stick to your choice

The fact is, you decided that day to sit in your car and settle the matter with a confrontation instead of going via police or insurance. And let's be clear here: the police and insurance both want you handling inter-driver disputes through them precisely because driving incidents are so very personal and emotional. There's a very long history of people being swept away by their rage into true stupidity. The whole point of their services is to stop you from doing exactly what you did, which is get all torqued up about it and seek confrontation.

So you made your choice, confrontation instead of police/insurance. Now, you should sleep in the bed you made. You had your confrontation and it didn't go your way. Sometimes you get the bear, sometimes the bear gets you, doesn't make you a coward, just makes you a human. You have to swallow your pride and deal with it. That's part of picking fights, you lose about half the time.

Yes, I know it can itch at your brain. It feels like a lack of closure. That's just wounded pride. Losing a square fight, then jinking around looking for ways to re-fight it, (aka holding a grudge), that's the act of a coward. You made your choice, stay with it.

Matter settled.

Is it possible that the perp is unaware that they damaged their, and your property? It might not be the case, that it was an intentional hit-and-run.

If I were you, I would send an email to the entire company appealing for witnesses or information, including the time and precise location of the incident.

In the event that no information is offered, the extensively photographed damage on the suspect's car should be turned over to the cops for investigation.

Your property was damaged. You should be entitled to compensation, regardless of who caused the damage.

Report her to the police. Use the dent as evidence. See if the police can get camera footage from nearby establishments that might be recording the parking lot.

Her being your boss doesn't matter at all. She hit your car, and if you can prove it, she's going to pay damages. That's all their is to it.

The chain of command is there to aid in getting things done. It's not there for you to cower in fear of losing your job every time someone above you does something. Fight back, the same way you'd fight back against anyone else.

Not sure why "Yell at my boss's boss" and "eat the cost" is a strict dichotomy here. Why can't you be nice about it?

Hey, Jane, the other day I noticed my car had been hit in a public lot. I happened to see your car and I noticed it had paint on it and a dent similar to the one that was on my car. Do you happen to know anything about what may have happened to my car?

A reasonable person would own up to hitting your car in this case (if they did it) and work it out amicably with you. Especially since she's your boss's boss, I presume she probably has the money to cover it.

Here's the other thing: If she doesn't come clean about it, that speaks a lot to her character as a manager. Managers need to be honest with their subordinates, about things like performance reviews, salary increases/decreases, projects and tasks, personnel changes, and so on. If she's not honest with you now, what makes you think she'll be honest with you at performance review time? It's unlikely you can get her fired (or even disciplined) over this as it's really not a work matter, but if you truly believe it was her but she won't own up to it, I'd look for a transfer out of her chain of command ASAP.

Where I live in the US the police are overworked even in "good" neighborhoods.

Call the police back with your case number.

Tell them you have information about the car that you believe hit you.

Give the police the description of the car, the license plate number, the fact that there was green paint on the (her) car, and that it is regularly parked in the same lot.

Send them a photo of the damage to her car which includes the license plate if possible (you don't want to be seen doing this probably... so consider it optional).

Optional:

Send an email out to the company with a description of your car, the date it was hit, and that insurance won't pay for the repair. Ask people to call the police non-emergency phone number with the case# if they have any information.

Keeps her from suspecting you if the police approach her about it.

Also gives her a chance to come clean (maybe she didn't know, maybe she did but would be willing to come forward because it is you).

Call the non-emergency number you were given regularly, to ask for updates.

Let the police deal with revealing to your boss's boss that she might be the perp.

Automotive paint is actually a highly distinctive blend of resin, solvent and pigment. Police will be able to collect a sample of that evidence and verify that paint on each car's bumpers matches the unique qualities of pain on the other car. This paint transfer is direct evidence, not circumstantial evidence. If you take the car to an auto paint shop and show an interest in what they do, someone will be glad to explain the myriad details involved in determining a paint match.

However with that informative bit said, do not start a criminal investigation into a work superior unless you were already planning on leaving. Once the police are involved, you can't un-ring that bell. People's pride and fears can make situations like this messy. Paint transfer may be proof of the crime, but your being fired as retribution is nearly impossible to prove.

You might be able to approach this as a private conversation with her, but consider this: If your hunch is right then you know she's irresponsible and unethical enough to commit crimes. And if your hunch is wrong you've effectively accused an innocent person of committing crimes. It's one of those gray cases where the right thing to do isn't necessarily the best thing to do. If I were in your shoes, I would most likely fix it and forget it.

To be honest, I somewhat disagree with others recommending absolutely avoiding the HR. It depends on your course of action. I would approach that person first and ask if it was her perhaps and maybe an amicable solution can be achieved.

If she denies responsibility, then file a police report and give them facts, i.e. that you thought it was your boss, however she denies responsibility, so you do not really know - this may point them to her direction. In that case I would also mention your course of action to your boss to prepare her that someone may ask her about it. This is obviously very thin ice, but I would mention it was necessary to file report to the police e.g. for better possibility of getting something from the insurance and you did have to state all the facts.

If, in fact, it gets confirmed that it was your boss who damaged your car, now it does become a workplace issue and you should talk to the HR. You may have an open, potentially legal conflict with someone in your line of management, so the HR might consider taking action to stop it being a workplace issue, e.g. proposing to reassign either of you so that the company is not in this sticky position. There are typically HR policies forbidding fraternising / love relationships between managers and direct reports to avoid protectionism, but I guess the only reason they do not mention relationships based on personal/non-workplace hatred is that it would be somehow weird, but it is pretty much the same thing and it should be avoided.

IANAL, but I have some experience with this kind of situations.

On the side of damage coverage: Depending on your jurisdiction, the way to go with car incidents happening in lots is to document the damage and file a complaint to the owners/caretakers of the lot. Especially if it's a ticketed lot, it is their responsibility to cover the damages, as from the very moment you pay, this constitutes a binding agreement that they are taking care of your vehicle, so any damages not directly your fault (e.g. you scratching your car against a column would not qualify, but a random stranger scratching it with their keys or car would) should be covered by them. The problem here is that you did not document/file the complaint the moment it happened and instead drove away, only to get back later. You can still fill the complaint, but any hopes of getting your damage covered will entail an investigation on their behalf, probably involving surveillance footage revision so they can check that on the day of the events, your car entered the lot without the particular piece of damage.

On the bright side, such investigation may prove your boss to be the culprit (although I am unsure as to what access you may have to the recordings); but, if this is the case, it does not matter as per the explained above: in the case of a parking lot, damages shall be covered by the caretakers, not the actual authors (if any) of the damages; so I would not address the situation with your boss in any case. Of course you can argue that she could have told you and then make ends meet with the parking caretakers, but that's beyond the point as far as workpplace relationships go.