There's a version of the Executive Assistant role that involves scheduling meetings, booking travel, and managing inboxes. Abigail "Abby" Moss does those things. She also does about forty other things that don't have titles, and she's been doing them long enough that most people at Floof Digital have stopped noticing where the company ends and Abby's influence begins.
That's probably how she prefers it.
Originally from Kings Heath in Birmingham, England / and she will correct you if you say "near London" / Abby came to the United States after several years working her way through increasingly demanding operations and executive support roles in the UK. She landed in Chicago, where she spent time supporting C-suite leadership at a large consolidated firm, before eventually crossing paths with Floof Digital's founder Derek Denney through a mutual friend, a coffee-stained business plan, and a borrowed conference room.
"I've always been drawn to companies that are actually building something. Not managing what already exists. Building."
Systems First, Always
Ask Abby what she actually does at Floof Digital and she'll give you a characteristically measured answer: she builds systems, and she protects culture. The two are not, in her view, separate things.
"A company's culture is visible in its systems long before it's visible in its values statements," she explains. "How decisions get made, how information flows, how people are brought into the organization / those are cultural statements. Whether you mean them to be or not."
This orientation toward systems isn't abstract. Abby is the person who personally manages onboarding for executive-level hires at the company, and she approaches the process with a thoroughness that goes well beyond paperwork. She's involved in the interviews, the transitions, and the early weeks of any significant hire / not because she's asked to be, but because she understands that the first ninety days of any senior role tend to define what that person becomes inside an organization.
Her instinct for this came early. Growing up in Birmingham, her father ran a precision-engineering firm / forty employees, long hours, the kind of operation where a bad quarter meant real consequences for real families. She watched him build something that people trusted, and she watched what that trust cost him to maintain.
"Companies fail when people stop trusting one another. Not when the market shifts or the product isn't right. That's what I took from watching him work. Trust is the actual infrastructure."
The Art of Productive Disagreement
One of the things Abby is known for inside Floof Digital is a very specific kind of candor. She doesn't avoid conflict / she approaches it in stages, with a discipline that makes it hard to dismiss and harder to resent.
"My first question when I disagree with something is always: have you thought this all the way through? Not as a challenge / as a genuine question. Because most of the time, that's where it ends. Someone talks through the logic out loud and they find the problem themselves."
When it doesn't end there, she writes a one-page summary of her position / structured, evidence-based, easy to read. And when she's exhausted those approaches and still believes something is wrong, she says so plainly. Then, once a decision is made, she commits to it completely and doesn't relitigate.
"I've been wrong. Notably wrong, on things that mattered. And I think being willing to be publicly wrong is the only way anyone actually trusts your judgment when you push back. If you're never wrong, people stop listening."
Detail as a Practice
Abby keeps a notebook system that borders on methodical. Right-hand pages record what happened; left-hand pages record what she noticed. Decisions get boxes drawn around them. Promises get starred. Every quarter she re-reads the starred entries.
"Promises are easy to make and easy to forget. The starring system is just a way of treating them as the commitments they actually are."
This attention to detail / to what was said, what was agreed, what was delivered / is part of what makes her effective in a support role that often operates without formal authority. She doesn't manage most of the people she influences. She influences them by being the person in the room who has read everything, remembered everything, and noticed the one thing everyone else let slide.
"Never Ask Someone to Do Something You Wouldn't Do Yourself"
There's a piece of paper by the coffee machine at Floof Digital. It's not laminated. It reads: Never ask someone to do something you wouldn't do yourself. It's been there since Abby joined, and the lack of lamination is intentional.
"The day it needs protecting is the day we've lost it," she says. "If it has to be permanent, it's already become decoration."
It's a small thing. But it's the kind of small thing that tells you a lot about how someone thinks about leadership / as a practice, not a position. As something that has to be demonstrated in ordinary moments, not announced in extraordinary ones.
Abby Moss has been demonstrating it, quietly and consistently, since she arrived.