Keila Gordon, MBA

Keila Gordon, MBAJul 20, 2026

In late April, I learned reMarkable would be downsizing headcount by 40%, about 300 of us. When they showed the new org chart, the enterprise department wasn't on it. By mid June, I'd be wrapping up my contract. Bummer, to say the least. But if you've spent any time in tech or SaaS, this is part of the gig. I'm incredibly proud of the work we did, though. We got reMarkable in the hands of executives at KKR, passed the rigorous security scrutiny of Sony, and carved a path toward AEC becoming a key vertical for us. As most people would, I've had my moments of frustration around the situation. I've been pretty public about picking up my life and moving my family across the country, so there have been a lot of big feelings attached to this. But a lot of people have asked me: would you have taken the role knowing what you know now? 100% yes. Life is short. Blink of an eye short. And I plan to live every moment of it, even if that means both flying and driving across the country with a very loud Siamese cat... twice. (I'm not traumatized or anything.) It's been a restorative time away from capitalism, and I'm looking forward to continuing to share what I've learned. As for what's next? You'll have to wait to find out 👀

Keila Gordon, MBAAug 14, 2026

I just wrapped up my second week as Head of Business Development within Higher Ed, at Protocall Services, Inc. They are a legacy company in behavioral health. Ten years ago I lost my brother Brian. He would have turned 40 this month. Instead of the blowing out candles, I get to celebrate his life by spending my days making sure students can reach someone the moment they need help. A few months ago I shared the story of losing him to suicide. I share it every year, but this year it took off. So many kind messages and comments. The support was overwhelming. When I shared how many people commented on the post, my mom cried. I had no idea that just a few months later I'd return to this work, providing mental health resources to students around the world. It feels good to be back somewhere that cares about this as much as I do. And as my family marks 10 years without Brian, we will continue to hold on to all the little winks he keeps sending us.

Keila Gordon, MBASep 14, 2026

An insurance agent emailed me about my new house before the ink was dry on the inspection report. He knew a concerning amount of details. The address. My agent's name. Probably my dog's name if he'd dug a little deeper. None of this was public yet. His email went straight to the trash. Unfortunately for him I was considering home insurance providers but his email made me uncomfortable. Here's what he didn't get: having the data isn't the hard part anymore. Anyone can pull it. The hard part is knowing when to use it, and how to use it, so it doesn't feel like you're being hunted (or stalked for that matter). That's the real skill in SaaS sales right now, and it has nothing to do with how much data you can pull on a prospect. The reps who win aren't the ones with the most information. They're the ones who know how to make a stranger feel like a person instead of a lead.