I am considering applying for a position at a large nonprofit organization, and I noticed that the Vice President of the department I would be joining is connected to me on LinkedIn. We connected about a year and a half ago after attending a CRM webinar together, where she impressed me with her knowledge. I did message her back then, and she responded kindly, but it's been a while since we last interacted. I'm aware that having a reference can significantly boost my chances of landing a job. I'm debating whether I should reach out to her on LinkedIn to let her know that I've applied for the position, even though she would be my boss's boss. It feels a bit awkward since we haven't spoken in so long, but I really need a reference to strengthen my application.