Keirsten Greggs

Y2K, Monster.com, and a Job Title She Had Never Heard Of

Greggs moved to the DC Metro area at the end of 1999, put her resume on monster.com because that is what you did, and got a call from a staffing company that decided she would make a great recruiter. She had no idea what a technical recruiter was. She did know that 2000 was coming, that the world was supposedly ending, and that if she was going to be around for it, the technical people had better be employed too.

The client list was a snapshot of an era: PSINet, MCI, MicroStrategy, plus a steady run of AOL provisioners, the people who made sure your line was actually connected. Northern Virginia being what it is, government contractors were everywhere, and one of them, a defense company, had HR practitioners handling recruiting rather than a dedicated recruiting team. That is usually why third-party firms get called in, she notes, to cover gaps, surges, hard-to-fill roles, or the requisitions nobody wants. Eventually that client decided to build the function properly and brought three recruiters in-house. Greggs was one of them, and defense and intelligence contracting became her home for most of her career.

All of This Is Prepaid

Ask Greggs about the people who shaped her and she resists naming favorites, because the list is long and she does not want to leave anyone out. Then she tells the story she has told for years. A candidate under consideration for an administrative assistant role at the State Department could not reach her office on the outskirts of Northern Virginia, so she drove out to meet him at a McDonald's, bringing a friend along to sit a few tables away. He arrived on public transportation, sharply dressed and entirely unbothered. He looked good, he told her, and every bit of it was prepaid, which was exactly why he needed the job. He got hired. He also got some more prepaid clothing.

The lesson she pulled from it has stayed operational rather than sentimental: do not judge a book by its cover in the wrong direction. People assume the polished candidate is fine, or does not need anything, or that someone else could do the job better. Greggs has seen the cost of that assumption from both sides of the desk. She still remembers the first time a candidate cried in front of her, and the person she helped after Katrina, and what those moments taught her about how much a job actually carries.

She learned the other half of her philosophy from a VP she supported, a serial startup builder who had come inside a large organization and kept operating like an entrepreneur, an intrapreneur before the word was in circulation. His advice was four words she has never let go of: "Know when it's time to go." When she was laid off from the large defense contractor where she had worked the longest, in 2016, she was told she would be fine. She decided she had had enough of waiting to be told, and built TRAP Recruiter instead.

Automation Yes, Autonomy No

Greggs is blunt about the AI conversation, in part because she thinks the premise is wrong. Talent acquisition has always been paired with technology, always chasing efficiency, always automating something. What is new is not automation but ambition: tools that are agentic, or want to be, and decisions handed to software that was never accountable for the outcome.

She uses AI daily and says so without apology. Claude is her coworker, she jokes, the collaborator she leans on because she is not a marketer or a business development person and often needs her TA voice translated for people who have never configured or implemented a system. What she will not do is let it decide anything. Handing a candidate conversation to a chatbot is where she draws the hardest line, and she will argue about it with actual friends in the profession. Her objection is practical. Siri does not understand her, and English is her first and only language, so she has resorted to British Siri. Now imagine that same system assessing someone whose English is a second or third language, and watch the bias compound: an accent becomes poor communication, typing becomes distraction, and a person with ADHD who needs something to focus on looks disengaged. Many of these tools make no room for accommodations at all.

Her broader warning is aimed at the buyers. There has never been a straight line from job opening to job filled, and there are too many variables for one to exist, which is why a human has to stay in the loop and own the decision. Stacking tech on a broken process, she argues, only automates the breakage. Tech will not fix an inefficient process and it will not build a process for you. Fix that first, then add the tools, and do not let a model write the job description you never read.

Advice for 2026: Read the Data, Then Rest

Greggs publishes a snapshot of the monthly jobs report, and for most of this year she has gone deeper than a summary post, pulling the figures apart and naming the data source so anyone can verify it themselves. That habit is the backbone of her advice to other talent leaders. Pay attention to the workforce. Pay attention to the job numbers. Recruiters lean naturally on relationship building, which she respects, but the moment calls for accountability, responsibility, and strategy over transaction. Filling a role is not the achievement; understanding what that hire does to the wider organization is.

She is candid that the current market is not making sense to her, and that she has grown less willing to defend hiring practices reflexively than she once was. The remedy she proposes is not cynicism but rigor: ask better questions, check the data, and make sure you are not making things worse. Then she adds the part most people skip. Give yourself a rest. You cannot run at one hundred percent indefinitely, and you need time that belongs to you.