You guys won’t believe what I just did recently. I stepped onto the other side of the desk and met with the enemy.
I recently went through the interview process for a Territory Manager position with Square. To be completely honest, I didn’t go in with a burning intention to jump ship—I’ve been running my own show for a long time. But curiosity is a powerful thing in this industry, and I wanted to see how the “behemoth” operates from the inside.
Here is what the journey looked like for someone who hasn’t touched a CV or sat for a formal interview in nearly two decades.
Dusting Off the Resume
The first hurdle was psychological: I haven’t had a job interview or a CV in 17 years. If you’ve been in the 1099 or independent sales world for a long time, you know your “resume” is usually just your portfolio and your reputation. Sitting down to document 17 years of hustle into a clean PDF was a trip down memory lane. It forced me to quantify my wins and sharpen my value proposition before I even hopped on the first call.
The Gauntlet: Back-to-Back Sessions
The process moved fast. My first interview was with a Regional Manager based in Boston. It was a high-level alignment meeting where he focused on Block (Square’s parent company) and their expanding ecosystem—moving beyond just the “white dongle” and into banking and software.
Immediately following that, I was ushered into a second interview with the Regional Manager for my specific area. This is where the rubber met the road. While there was some “get to know you” talk, the core of this session was Roleplaying. They wanted to see how I handled objections and how I positioned Square against traditional ISOs.
The “Pass” and the Post-Game Analysis
A few days later, the email landed from the recruiter: They decided to pass on me at this time.
I’ll be honest—I was oddly bummed. Even though I wasn’t sure I wanted the job, the competitive nature of a sales professional hates “losing” a deal. Looking back with the “post-game” clarity we usually reserve for lost accounts, I can pinpoint where I dropped the ball:
- I Winged the Roleplay: They sent over specific instructions beforehand. My “old school” ego kicked in—I figured I’d been doing this for 20 years and could just roll with it. In a corporate ecosystem, they aren’t just testing charisma; they’re testing your ability to follow a specific internal process.
- The Missing Paperwork: Despite getting chat to use my LinkedIn info to create a new CV, I realized I never actually got it over to them. In the corporate fintech world, if it isn’t in the system, you don’t exist.
The “Aha!” Moment: The ISO Disconnect
Despite the rejection, the most amazing part of the experience was a question I asked all three people (the recruiter and both managers):
“What’s the deal with ISOs being able to sell Square now? If I’m the Territory Manager for Mississippi, why would Square allow independent agents to move the same product in my backyard?”
The response? Complete blank stares.
Not the recruiter, and neither of the Regional Managers, had any clue what I was talking about. They actually reassured me that Square wasn’t doing that. As veterans in this space, we know better. We know Square has been opening up channels for independent agents.
Yet, here were the W2 employees—the people actually running the ship—who were totally in the dark about their own company’s channel strategy. It was a massive reminder that the Corporate Silo is real. These managers are so focused on their internal “Block” training that they don’t even see what the partnership wings of their own company are doing on the street.
The Final Verdict
I might have been passed over, but I walked away with my head held high. This experience was a healthy reality check. It reminded me that while the “Big Tech” players have the fancy branding and the streamlined processes, they often have massive blind spots regarding the actual market.
I’m heading back to my current grind with a little less ego, a little more respect for “the process,” and the realization that I clearly have a better handle on the industry landscape than the people who were interviewing me.
Have you ever interviewed with one of the “Big Tech” processors only to find out you knew more about their business than they did? Let’s talk about it in the comments.
Happy Selling,
David
