Should I leave my very flexible but slightly underpaying job?

I’ve been at my current role for 4 1/2 years. I started as an intern and received a full-time offer four months later. At the beginning of COVID, I had grown extremely unhappy with my company as well as my direct manager and had actively started looking for other jobs. I was making $48k at the time and received offers for $60k and $80k. After COVID, we went permanently remote and I also got a new manager who was a huge improvement from my previous one. Currently, I make about $63K, which after some research is about $5k under market value for my title and experience. We get an annual bonus ranging from $2k-$4k, and occasionally have received a Christmas bonus of $500-600. We receive unlimited PTO (I’ve taken about 3 weeks total vacation this year), we get an additional week-long vacation in June as well as December (Christmas-New Years Day). We have a company wellness program that offers rewards such as airline miles/plane tickets and hotel points/stays. My weekly schedule is extremely flexible and we typically take off early on Fridays.

The *only* negative is that each and every time I have broached the topic of a merit raise, I am met with instant and borderline angry pushback. This pushback has absolutely nothing to do with my performance, as other people have met with similar pushback. I have been told by a senior leadership member who owns several acres of land that I need to have a good, non-financial reason for wanting a raise. I’ve been told that asking for additional compensation based on being assigned more duties was “not a feasible conversation” due to leadership launching a salary evaluation software; when I asked what this had to do with getting compensated for extra duties being given to us, the person became visibly angry/uncomfortable, and changed the subject. Additionally, I’m friends with our controller, who has revealed that our company has made some concerning financial choices: a salesperson who’d been fired for several months was still receiving commission from past deals; another team member was being $20k underpaid in comparison to their other team members, and it took months to get the problem corrected; our CEO and CTO are resistant and often hostile to suggestions of raises or even title changes for members, on the basis that “it shouldn’t be about money” or “that’s just how we do things.”

As mentioned above, we are launching a salary evaluation software that’s supposed to help launch these conversations and bring us all up to rate. But I’m beginning to feel like upward mobility is simply never going to be a reality at my company, and I also know that the best way to boost salary is to jump companies. As much as I enjoy our flexibility, I’m also beginning to feel very unmotivated and uninterested by what I do. At the same time, I’m really scared of the unknown. My partner wants me to jump, and some of my coworkers have said I shouldn’t stay much longer. I struggle with what I value more – my personal time or increasing financial gain so I can start reaching some personal goals. I guess I would love to receive some third-party insight, if possible.

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