Keely Flood

From the Sideline to the Search

Flood came to recruiting out of college football. He had spent five years coaching, and a good share of that time recruiting high school athletes to play D2 and D3 ball, which is to say selling an opportunity without the leverage of a full ride. When he decided to leave coaching and get back to the Chicagoland area where he was from, his ambition was broad and blunt: he wanted to get into sales, and he did not much care what he was selling.

The conversation with that agency recruiter reframed everything. Once she explained what she actually did, Flood ran the math on his own resume in real time. "Well, I coached and recruited high school athletes," he remembers thinking. He decided he would sell that single skill in every interview he took, and from that point forward he applied only to agencies. He landed at Medix. When a leader there walked him through the career path, his first question was how fast he could get into the sales seat. The answer was that he had to start in recruiting. His sole focus became getting promoted, and the recruiting seat he treated as a waystation became the foundation of an eleven year career.

The Email That Reframed the Job

The most formative moment of Flood's career did not come from a mentor. It came from a candidate he still refers to as Kim L, a name he protects out of respect for her privacy but has never forgotten. It was 2015, he was still in the recruiting seat, and his operating model was uncomplicated: fill roles, make spread, repeat. He placed Kim in a data entry role at a client called Dearborn, a company he is not sure still exists.

Then she emailed him. The job had given her proof of employment, and that proof let her keep the apartment where she and her child were living. Medix built its culture around the idea of positively impacting lives, a mantra Flood had heard plenty of times without fully absorbing it. Kim's note, he says, hit him right between the eyes.

It also taught him the inverse. If a recruiter can make a life measurably better, a careless one can push a career in the wrong direction just as easily. That symmetry has stayed with him and shows up in the standard he holds himself and the industry to.

Sit Down and Watch Me Run This Thing

When Flood finally reached the sales seat, two people taught him how to occupy it. The first was his boss, Dan Dumroff, who is still in the space. Ahead of a client meeting at Now Foods in the Chicagoland area, Dumroff gave him the least ceremonious piece of coaching imaginable: sit down, shut up, and watch me run this thing. Flood walked out of that room genuinely stunned by how the meeting had been conducted, by the questions asked, by the sequencing of it all.

The second was Alex Johnson, a sales rep Flood still describes as one of the best he has ever been around. He shadowed both men relentlessly in his first stretch on the sales side, and the lessons on how to sell and what to look for have outlived the jobs where he learned them. That apprenticeship model now sits at the center of the advice he gives to everyone entering the field.

Buying Back the Forty Minutes

Flood is an acronym guy, and his favorite is RGA: revenue generating activities. His case for AI is built entirely around protecting them. Administrative work is a structural tax on this profession, and he has spent real effort engineering it down. Inside CoWork he has built a set of workflows himself, so that he can come off a call, issue a single prompt, and watch a task that used to consume 45 minutes complete in four or five. That is roughly 40 minutes bought back after every meeting, which converts directly into more conversations. He knows of no better proof of future success than talk time.

He is considerably less charitable about the rest of it. Prospects have never been more spammed, he argues, buried under AI slop from people who are frequently not even in the industry, each claiming to have built the go to market tool that will replace everybody. Recruiting has taken some black eyes over the years and has its share of bad actors, and Flood believes the flood of automated garbage has deepened the mistrust that candidates and clients already carried. His challenge to the true believers is pointed. "Point to me a person who's willing to trust their job search to an AI chatbot," he says. "You won't find one."

The conclusion he draws is optimistic for anyone willing to do the harder thing. The human element, meaning the phone call, the face to face meeting, or at absolute minimum a video call, is becoming a premium in this space. If you cannot hold a conversation and cannot make judgment calls, he says plainly, you will not make it in this business over the next decade and beyond.

Model the Masters

Asked what he would tell someone brand new to recruiting, Flood could not hold it to one thing. Start by knowing your prospect's world. Learning the mechanics of the job is unavoidable and takes time, but the people who last are the ones who understand the industry they sell into and what actually fills their prospects' days.

Second, do not be afraid to ask for help. If you work inside an organization, position yourself side by side with the best reps in the building. If they are on calls, ask to be on them. If they are taking meetings, ask to shadow. "Model the masters" is a phrase he picked up long ago and never let go of, and it is the same behavior that put him in the room at Now Foods watching Dan Dumroff work.

And third, get comfortable saying three words: I don't know. It is the least glamorous advice on his list and, coming from someone who once had to ask a stranger to explain what an agency recruiter even was, arguably the most credible.