Failure is not an option: SaaS, Print, and Digital Ads background. 3 years of grit, just hitting a wall
I’m at my wit's end, but I’m a closer and I refuse to quit. I have a heavy background in SaaS, Print, and Digital Ad sales.
The Wall (The Gap):
My resume has a gap that was initiated by COVID, which I used to start a family and travel. However, I haven't been sitting idle; I’ve spent this time identifying and mastering the AI programs and systems needed to stay competitive. In my past tenures, I’ve always been a high-performer—regularly working overtime from home by choice because I love the hunt. I’ve always worked for a base + commission, and when I’m hitting my numbers and enjoying the work, I’m at my best. This is also where my remote experience and self-management skills come in.
The Hustle:
I am now using AI to help me tailor my resume for every single lead and writing custom cover letters for every application. Despite the effort, the background, and the technical upskilling, I’m not even getting bites right now.
What I’m Looking For:
I am looking for a remote role with a solid base salary where I can drive revenue and results. I’m platform-agnostic—I’ve sold software stacks and high-end digital/print campaigns. I know how to speak the language that gets the contract signed and I understand the marketing strategy behind the sale.
The Ask:
I need a reality check—what am I missing here?
Is a COVID-initiated gap still being judged this harshly, even with upskilling?
Is the AI-tailored resume approach actually backfiring?
For anyone in the space: Are there specific industries or companies currently valuing consultative SaaS/Ads experience for remote roles?
I'm ready to get back into a role with a solid base where I can drive revenue. Any insight on how to break through this wall would be life-changing.