Might be getting an offer from an old boss I like. No bump in salary, more responsibility, more bonus, and equity, perhaps even a sign-on bonus. So why am I hesitating?

I’m in digital marketing and have been for more than 15 years. SEO, SEM, reputation management, social media, PPC, UX/UI, I’ve worked with brands you’ve probably heard of.

Years ago I had the chance to move to a new company where the work was OK but my boss was/is really dialed in to me as a person. Someone who knows this is just work, that we’re here to help our families, and is a bulldog when it comes to defending her people. I stayed there a year and a half before I was poached by a big brand. I’ll lay out the dollars and cents because transparency is important: I was at $165k w 20% bonus potential and this new company offered me $215k with a 20% bonus plus a jump in title to VP of digital marketing.

I worked in one state and lived in another, which is important to know. While the people were great, I was the face for this franchise and I was dealing with 500 franchisees who saw me as their personal help desk. 7 days a week I was working and had a boss who made my remote work situation (which I negotiated, 3 days in the office, 2 days at home) miserable by telling me I had to be in town for things that would pop up on her schedule. I would literally have to change flights and eat the change fee (I’m still burning over this) and my boss said, essentially, tough s&@$. She wasn’t mean, just matter of fact. I helped implement a new CRM, mobile app, and launched a brand new website in 6 months.

Fast forward 9 months from when I started and my old boss came knocking. She begged me to come back and help her righten a ship that had gone very off course. The one thing I cared about more than anything was just being home with my kids as that was the whole point of my leaving in the first place and she said I could stay home all the time, just come in 3 days a month. Also, she wouldn’t be able to match my salary. How did $175k sound? It sounded crappy, to be honest, but she kicked me a $10k signing bonus.

Enter the pandemic and in June of last year she was transitioned out. I crushed goals by keeping the business flush with leads and helped to restructure our site so that Google would look at it more favorably. It worked and our organic traffic started to recover well past the hit it took. My new boss, who I was nervous about, has been fine. Very genial, very kind, understanding, knows his way around an Excel spreadsheet like no one’s business and is super collaborative. Thing is, it’s just me and my director of marketing, THATS IT, plus our agency and vendor partners. I’m doing good work by staying on top of enhancing our site while supporting his efforts. Still, the Panda Express made sure no one got bonuses last year. We’re on track to maybe get one (I’m eligible for 20%) this year.

Lo and behold, my old boss came knocking last week. She’s now heading a privately held/private equity backed, 1,100 location business that did alright even through the panda. Pretty much gave me an offer to help her at her new gig. Same title, same base pay (which I’m not thrilled with as I took a pay cut to work with her at my current gig), BUT with a possible sign on bonus, 40% bonus opportunity, AND some undetermined amount of equity (I’m still working through the details) but she’s telling me they’d be looking to sell in ~2 years. I’ve never had equity before so that’s new and, from I’ve heard, could be very awesome if everything goes to planned. I wouldn’t have to travel, either, to the new HQ which is in a different state for both her and me.

Still. I’m hesitating. And I don’t know why. This panda has taught me that I’m good at what I do and I’ll do anything to keep my family going. I’ve never had an issue with my current boss and I’m pretty comfortable with my level of responsibility for what I’m paid. I certainly wouldn’t take another pay cut but maybe I’m still perturbed about the salary being the same? Then the other side of my brain is looking towards a more financially beneficial future but even my more base instincts aren’t lighting up at the prospect of more money like they did for the job I had before this one.

I’d definitely have more responsibility managing a few people along with being the director but that’s why I wanted to come to Reddit just to lay it bare and see if someone can pick up on what I’m putting out there and knows what this hesitation means or if there are certain questions I need to ask myself or if I’m always going to be seen as meat to an organization and I just need to “get mine” no matter how friendly a situation I’m in now.

Any advice is going to be much appreciated.

TL/DR: I have a chance to get real equity that is going to cash in in about two years, receive a bigger bonus, manage a few people, but still stay at the same salary I’m at now at a job that has less responsibility but is still OK

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