Hiring Is a Culture Decision, Not a Headcount Decision

Every company says culture matters, but the real test happens during the hiring process.

I’ve been CEO of DealRoom for more than six months now, but over the past two years, I’ve been building this leadership team, and hiring into it, first as COO, then as President, and now as CEO. In that time we’ve more than doubled our revenue and our customer base, moved into a new office in Boston, and gone from a small team to something that actually looks like a company.

If there’s one thing I’d tell any founder or operator who’s about to scale past the “we all know each other” stage, it’s this: your values shouldn’t just be a slide in the onboarding deck.

Don’t get me wrong, I didn’t walk into DealRoom with a fully formed philosophy on this. I learned most of it by hiring people who were talented, but not a culture fit. If you’ve done this before, you know how the story goes. Someone interviews well, checks every box on the skills side, and gets hired even if they don’t fully align with what we’re building and how we’re moving. 

Over time, that misalignment becomes extremely clear. It never has to do with whether the person is smart, talented, or capable of getting the job done. It’s whether or not they fit the culture and have the same growth mindset as the rest of the team..

Culture doesn’t sort itself out. You have to hire for it on purpose.

At DealRoom we’ve got three core values that show up everywhere: Deliver the Wow, Be Kind & Direct, and Own It. Here’s how each one actually shapes who we hire and who we don’t.

Deliver the Wow Means the Candidate, Too

We talk about Deliver the Wow mostly in the context of customers and prospects. It’s the standard we hold ourselves to on every deal our platform touches. But the value is explicit that we WOW our customers, partners, and teammates, and teammates includes the people who haven’t said yes yet.

I track a metric I call CCR, Candidate Conversion Rate: the percentage of our top-choice candidates who accept the offer when we make it. It’s not a vanity number. We’re competing for talent in Boston against established names like HubSpot and Klaviyo, and hot AI startups building hubs here too.

Compensation alone doesn’t win that fight. What wins it is whether a candidate feels the wow during the process itself. If your hiring process is clunky, you’re not just losing candidates, you’re showing them exactly what it’ll be like to work with you.

Be Kind & Direct is the Best Interview Signal I Have

The value has three parts: care deeply, go direct, communicate thoughtfully. On paper it reads like a nice-to-have. In practice it’s the single best predictor I’ve found of whether someone will actually work well on a team that debates hard and moves fast.

Picture the scenario every company has lived through: Employee A is frustrated with Employee B. The common move is Employee A vents to their manager, that manager has an awkward side conversation with Employee B’s manager, and eventually, maybe, Employee B hears about it secondhand. That pattern erodes trust and rarely fixes anything. We’ve codified “go direct” as a Core Value specifically to kill that pattern, and it changes what I listen for in an interview.

I’m not asking whether a candidate has had conflict because everyone has. I’m asking what they did with it. Did they go around the person, or did they get in a room and say the uncomfortable thing directly? If someone’s instinct is to smooth it over instead of name it, that’s not a quirk I can coach later. It’s a values mismatch, and those compound.

This is also where I’ll push back on something I hear from other founders: that a collaborative culture means getting everyone’s input before deciding anything. Consensus-driven management results in watered-down decisions. Don’t get me wrong, getting input from all key stakeholders is critical, and the magic really is in the debate, but there’s a difference between collaborative and consensus-driven.

We practice disagree and commit on purpose. We debate hard because we care deeply and when we hit a crossroads, someone accountable makes the call, and the people who disagree commit anyway. I’m hiring for people who can do that last part. A candidate who needs everyone to agree before they’ll move is going to slow a team like ours down.

Own It Shows up Before Someone’s Even Hired

Own It means we take pride in our work and don’t wait to be told what to do. We’ve built that expectation directly into how we hire.

Instead of writing a job description and hoping for the best, every hiring team runs through a structured process: each person on the hiring team submits the competencies they think matter most for the role, we synthesize the list, then the team votes to rank what’s actually required versus preferred. It might sound like overkill for filling one seat. It’s really just Own It applied to hiring itself and refusing to leave something this important to a generic template or one person’s gut call.

Own It also means treating hiring as urgent, not a side project. Being a bootstrapped, frugal company forces us to make hard calls about where we invest, hiring included, and I’ve come to see that constraint as a feature, not a bug. Every quarter, our leadership team sits down and asks a version of the same question: how are we living our Core Values, and where are we falling short? Hiring is always part of that conversation, because getting it wrong is one of the most expensive mistakes a growing company can make.

Turn Your Values to Actions

None of this means we’ve gotten hiring right every time. What’s changed is that when we get it wrong now, we can usually point to which value we ignored in the process, which is at least a more useful mistake than “the resume looked great.”

If you’re building your own team right now, here’s the actual advice, not the poster version: pick the two or three behaviors that actually predict whether someone thrives at your company, build a real interview question around each one, and weigh the answers. It may slow your hiring down slightly, but it will save you months of cleanup later.

We’re still learning this as we go, which is part of why I like sharing it. If you’re figuring out the same thing at your own company, I’d genuinely love to hear how you’re approaching it.

About the Author: Greg Lord is CEO of DealRoom, the M&A platform behind Buyer-Led M&A™, where he’s leading the company’s next phase of growth after two years as COO and President that saw revenue and the customer base more than double. Before DealRoom, he held go-to-market leadership roles at VergeSense, Elastic Path, and SmartBear, and holds an MBA from the University of Notre Dame’s Mendoza College of Business. A first-time CEO, Greg writes candidly about the realities of building and leading a company, from hiring and culture to disciplined dealmaking.