Welcome back to the text recap of The Paycast Network! Sponsored by Cygma—a direct processor engineered for faster payments and higher profits—we are bringing you an easy-to-read breakdown of our latest deep-dive episode.
In this episode, host Chase sits down with a true fixture of the merchant services social media community: Andrew Gill, founder of Gill Payment Solutions based out of New York.
Andrew’s career path is a masterclass in self-education, execution, and navigating the critical transition from a structured corporate W2 sales role to the uncapped freedom of a 1099 independent agent. Whether you are a brand-new agent looking for your footing or an industry veteran checking your blind spots, Andrew’s “in-the-streets” insights offer major value.
Warming Up: New York City Trivia
As a proud New Yorker, Andrew was put to the test with some city-specific trivia. See how well you know the Big Apple:
- The Original Name: Before it was New York, the city was established as a Dutch settlement in the 1600s called New Amsterdam. It was renamed New York in 1664 in honor of the Duke of York after the English took control.
- A Building with Its Own ZIP Code: Because of its sheer massive scale and the thousands of businesses operating inside it, the Empire State Building actually has its own dedicated ZIP code: 10118. It is one of just over 40 buildings in Manhattan with this distinction.
The W2 Hustle: Self-Education and the Stairwell Interview
Andrew’s journey started around 2008–2009 at a small independent sales organization (ISO) in Scarsdale, NY. Like many newcomers, he was given almost zero formal training. His manager simply told him to make cold calls and see if he could make something happen.
Instead of getting discouraged, Andrew took his education into his own hands:
- He kept a legal pad by his side and scribbled down every industry term or acronym he overheard in the office (like First Data or MPC).
- Every night, he would go home and Google those terms until he completely understood how processing platforms operated.
When his manager went to the gym for two hours one afternoon, Andrew used his self-taught knowledge to break down a merchant statement, pitch an effective rate, and successfully close a deal on his own. Instead of being thrilled, his manager felt threatened.
Realizing he needed a structured corporate environment to truly scale, Andrew found an open Account Executive position at First Data partnered with CitiBank. To avoid getting caught by his current boss, Andrew conducted his entire First Data interview inside the office building’s concrete stairwell during his one-hour lunch break. He landed the job, managing 15 to 20 CitiBank financial centers across Westchester and Rockland County, where he mastered the core mechanics of statements, deposits, and corporate scaling.
Shifting to Leadership: Coaching vs. Managing
Andrew eventually moved up into sales management, leading a team of 16 to 17 representatives at Bank of America Merchant Services between 2018 and 2021.
Because Andrew had just come from direct, feet-on-the-street selling, his management style was wildly different from career corporate executives. He looked at himself as a coach rather than a boss:
- The Monday Touch Base: Every Monday, after the standard team-wide call, Andrew would personally call his reps. He categorized them dynamically as A, B, or C players to tailor his coaching style.
- Focusing on the “Why”: For top-tier “A” players, he checked in briefly to see if they needed any roadblocks removed. For struggling “C” players, he focused heavily on confidence-building, uncovering their personal motivation, and tweaking their tactical pitch.
- Carrying the Bag: To motivate his team to sell more point-of-sale (POS) systems, Andrew made them a promise: “If you sell your first Clover POS system, I will personally drive out to the merchant’s location and do the installation with you.” Alleviating the technical anxiety for his reps caused team sales to skyrocket.
The Leap to 1099: “32 Flavors” of Freedom
When Andrew and his wife were expecting their third child, he made the deliberate choice to leave his secure corporate W2 job and transition into a 1099 independent agent under his own banner, Gill Payment Solutions. He wanted to completely remove the corporate cap on his earning potential.
The transition was incredibly smooth because he treated his independent business with the exact same military-grade discipline he learned in the corporate world. Andrew notes that as a 1099 agent, “what you eat is what you kill,” meaning self-discipline is your ultimate currency. He even jokes that his middle daughter, Destiny, acts as his family “CEO”—regularly calling him at 2:00 PM to demand a full report on his daily cold-call stats!
Beyond the uncapped financial upside, Andrew highlights the massive advantage of product freedom:
“On the corporate side, you are entirely constrained by whatever technology your specific brand dictates. On the 1099 side, I like to say we are the Baskin-Robbins of the payment processing industry. I’ve got 32 different flavors of technology. If a solution doesn’t fit a merchant’s exact needs, I don’t have to walk away from the deal—I just pivot to a different flavor that does.”
Keeping Clients for Life: From Audemars Piguet to the Pandemic
While many agents chase upfront bonuses and then disappear, Andrew has successfully retained marquee clients across multiple career transitions, company moves, and structural changes. His retention strategy relies on two pillars:
1. The “Sundown Rule”
Inherited from his days at First Data, Andrew operates on a strict rule: Every single merchant phone call or email must be answered before the sun goes down that exact same business day. Even if he doesn’t have the final solution to a technical glitch or billing issue, he reaches out to provide an interim status update so the business owner never feels abandoned in the dark.
2. Patronizing His Own Portfolio
If Andrew is traveling through an area where one of his merchants operates a restaurant or retail boutique, that is exactly where he stops to eat or shop. Supporting the people who support his business builds ironclad, decades-long loyalty.
High-Profile Portfolios
This relationship-first model has allowed Andrew to land and manage some truly legendary accounts:
- Audemars Piguet (AP): Around 2011–2012, Andrew landed the prestigious Swiss luxury watchmaker as a client through a CitiBank referral. They wanted to establish a massive corporate banking relationship, but they explicitly refused to move forward until their merchant services were set up flawlessly because their business was entirely credit-card driven. Andrew successfully structured their high-volume processing across their Clearwater, FL location, their flagship NYC boutique, and their primary luxury service center. Fun fact: Andrew noticed during his meetings that because of strict brand culture, no one in the corporate office wore a watch unless it was a handcrafted Audemars Piguet!
- The Empire State Building: While operating at Bank of America Merchant Services, Andrew managed the merchant processing portfolio for the iconic landmark. This responsibility coincided directly with the onset of the COVID-19 pandemic. Andrew had to navigate the unprecedented logistical challenge of managing credit card processing, refunds, and adjustments for one of the most heavily trafficked tourist destinations on earth during a total global lockdown.
Catch The Paycast Network Live at SEAA!
Are you ready to elevate your independent sales game? The Paycast Network will be traveling to Miami, Florida starting June 8th as an official media partner for the SEAA Conference!
We will be set up right outside the main expo hall broadcasting live, interviewing top processing executives, and hosting our signature interactive road game: “Sell Me the Duck!” Stop by our booth, chat with Chase and the crew, put your sales techniques to the test by trying to sell us a rubber duck, and you could win some incredible prizes. See you in Miami!