“Close to half of our final round candidates will wash out.”
The hiring playbook most founders are still following was written for a different world.
We just wrapped a conversation with Michelle Volberg, founder and CEO of tech-enabled recruiting and referral platform Twill, and Ryan Denehy, founder and CEO of ITaaS provider Electric.
The topic was your first ten hires. What’s changed, what hasn’t, and what founders are getting wrong right now.
TL;DR: AI proficiency is now a baseline screen for every function. Lack of stage fit still predicts failure faster than almost anything. Provided references will never surface the real story, so you have to back-channel (yet so many hiring companies rarely do). And take-home assignments are effectively useless now that everything gets done by AI.
This virtual event was presented by Twill
Twill gives you warm introductions to the top 1% of technical and non-technical talent your team actually wants to hire, handpicked by trusted leaders in tech. Every referral comes from our curated network of top engineers & operators who vouch for the best talent in their circles.
What changed, what didn’t
If Ryan were building company four right now, the biggest shift from his first three would be one thing across every hire:
“What would change with my very first hires is AI proficiency regardless of the function in the business that you’re working in. There is a rapidly increasing expectation that whether you’re in finance or HR or sales, that you just are gonna start to have a much higher level of technical proficiency.”
Michelle frames the filter differently than most founders do. It’s no longer about what needs to get done. It’s about what requires human relationship or judgment that AI cannot duplicate or replace. What hasn’t changed? The importance of stage fit match between the company and the candidate. Ryan calls it “probably one of the single biggest predictors of whether or not somebody’s gonna work out, particularly in those first ten hires.” And early-stage is a specific kind of hard. Someone experiencing it for the first time while you’re trying to build a company is a risk founders chronically underestimate. And being able to see if the candidate is truly mission aligned with the company is another. When a candidate isn’t genuinely connected to what the company is doing, six days a week will eventually produce the thought “why am I doing this?” And then they leave.
Ryan’s tell for mission alignment doesn’t come from any questions that he might ask. It comes from the candidate, unprompted. As he told us:
“Some of the best people we hired were at some point in the interview process, they would almost be selling us on the opportunity. Like, ‘This market’s huge, and no one’s done this before. Why aren’t more people talking about this?'”
Two things that will get you the wrong hire every time
Michelle put it plainly:
“Hiring the wrong person is the most expensive mistake you can make.”
She went on to talk about the pitfalls of relying on provided references. No one is ever going to give you a bad reference. You have to back-channel. Ryan’s team found that close to half of their final-round candidates wash out once they do. Not always dramatically or due to skeletons in the closet. Sometimes it’s just a cultural mismatch that would never come up in an interview. He illustrated the point by sharing the story about a VP-level revenue candidate who flew through Electric’s process before a back-channel surfaced that they were “the smartest person in the room … and want to make sure everybody knows it.” That’s the kind of thing you only find out if you ask the right people.
And those take-home assignments everyone seems to love giving during the final stages of the interview process? Michelle did not mince words:
“Please don’t send take home assignments. You don’t even know if they did it. Everything is done by AI. If you wanna really assess for proof of ability, do live sessions. Do live coding sessions. Do live sales questions. Do everything on Zoom. Watch their eye movements so they’re not reading answers off, and don’t prep them.”
Sell first. Scare second. Don’t mix them up.
Founders have to start with the sale. Michelle described coaching a well-credentialed founding team whose candidates were consistently dropping off after round one. The feedback she kept hearing was that the founder came across as condescending. No pitch, no vision, just “why are you the right fit for this role?” as an opening question.
“You should go in there and assume that this is your dream candidate, and you just don’t know it yet. […] Pitch them for five minutes like it’s your dream candidate. Once the candidate understands your founding story, why you’re building this company, your mission, your vision, then you can kind of go into “scare mode and interrogation mode and figure out if they’re the right fit.”
Yes, that scare part is critical, too. This was advice she received from one of her investors, Roy Bahat of Bloomberg Beta. Be honest about how hard it is, how unglamorous it gets. Ryan does a version of this with candidates as well. He compared it to a founder pitching a VC and including a “reasons not to invest in this company” slide in a pitch deck. The best candidates hear the hard stuff and get more energized, not less.
At some point, the candidate does need to believe, without needing to be continually sold. As Ryan put it:
“At a certain point in the process, you should not have to be convincing somebody to come work for you. If you’re still selling all the way at the end, that’s a bad sign.”
Recruiting is a long game
Recruiting has to become a strength of the founder, not something handed off to a firm or a Chief of Staff or whoever has the spare cycles. When a founder personally reaches out to a candidate, the response rate and the quality of attention from the candidate changes. Ryan hired a CMO at Electric where the timeline and approach illustrates the point. He reached out to her when the company was seed-stage. She said she was happy to give advice but wasn’t leaving her job. Years later, she emailed him:
“I’m looking around, and I’ve kept track of you guys. You wanna talk?”
She was hired and ended up working there for four years. An eternity in startupland and more importantly, the mark of a great candidate fit.
Watch the full conversation for more from Michelle and Ryan on how to work with external recruiters effectively, the chief of staff question (and whether you actually need one), and the title inflation trap—including why Ryan spent eight months searching for a CTO when he actually needed a senior director of engineering.
