In our ongoing interview series with forward-thinking HR and business leaders, we spoke with Seth Rogers — an advisor who helps growth-stage companies align their hiring, incentives, and organizational structure as they scale. The South Carolina–based people strategist has worked across recruiting, benefits, and go-to-market roles at companies like Toast and Favor, and now partners with founders, CFOs, and HR leaders to ensure people strategy doesn’t become a growth bottleneck.

Rogers recently spoke with Basic Capital about what employees actually value in a benefits package, how structure (not just autonomy) shapes performance, and why middle management is often where strong talent stalls out. 

The following is our conversation, edited for length and clarity.

Basic Capital (BC): You’ve been in the hiring and talent world for a while. Would you say American workers today are more in a “live to work” or “work to live” mindset?

Seth Rogers (SR): Among millennials, I think we’re seeing a shift toward “work to live,” but it’s more nuanced. It’s easy to parody as entitlement, but a lot of people understand the tradeoffs. If someone wants to be at their kid’s soccer game on a Tuesday afternoon, and their employer supports that, they also know it might cost them a promotion. And many are okay with that. It’s not that ambition is gone. Quality of life and agency are more consciously factored into the equation.

BC: That’s a healthy tradeoff, but how is it actually playing out in the real world? It’s a wild employer’s market out there right now. Isn’t there a stronger pull toward grinding people down rather than meeting them halfway?

SR: It depends a lot on the size and maturity of the company. When I was at Esurance, we used to run what I called “speed dating” interviews. Fifteen-hundred people would show up at a hotel in Tampa, and we’d do rapid two-minute interviews. “Convince us you want a sales job.” 

It was all about volume. We were hiring people to take 100 inbound calls a day and close 25–30 of them. That kind of high-pressure model doesn’t fly as much today. Even large organizations have become more selective because they’ve seen how expensive turnover is. But smaller companies, especially ones in hyper-growth mode, still expect candidates to be Swiss Army knives — adaptable, broad skill sets, with little room for error.

The problem is, there's often no margin to see someone’s potential. There’s no space to let them stumble a bit in the sandbox. If you want people to grow into the role, you have to build in a little slack. But a lot of companies are playing a different game. They're focused on survival, not development. And job seekers often don’t realize how much that influences what the employer is really optimizing for.

BC: So in many cases candidates are largely expected to be flawless from the get-go, but are they approaching the job search the same way?

SR: Not really. Most applicants are doing what I’d call a shotgun approach: applying to a hundred-plus jobs with generic resumes. But you can’t blame them. Job descriptions are often nearly identical, yet the cultures and expectations are wildly different under the hood.

Ironically, I think a lot of these folks would thrive in smaller companies where they can take on more responsibility and actually build something. But smaller companies under 250 employees can’t afford to wait for potential. You have to prove your value up front.

BC: What should employers be doing to attract and keep the right people?

SR: Build better benefits packages. Especially for younger workers, who often don’t care much about health insurance. They assume they’re healthy and invincible. But what they are asking about is the long-term — retirement, ownership, financial security. That’s where you can speak to their deeper priorities.

If you’re working to live, then you want to know: “What am I building up for when this work part of my life is over?”

BC: Are most employees financially prepared for that conversation?

SR: Honestly? No. Most people, college-educated or not, are financially illiterate. They don’t understand compound interest. I’ve had to explain retirement basics to 23- and 33-year-olds alike.

So if you're building a total comp plan, you need to think about your whole workforce. Single or married, with or without kids, early- or mid-career. You need offerings that meet people where they are, and that includes things like investment support and flexible work arrangements.

BC: So you’re not just adding perks. You’re designing for different life stages, roles, and needs.

SR: Exactly, and when you’re hiring from a strong position, you can afford to be choosy. But that means you owe people something too. You have to give them a path. Tell them: “Here’s what we saw in you. Here’s your potential. Here’s the track.” That’s how you retain serious talent.

And let’s be honest. The biggest threat to retention is bad middle management. So many companies are bloated with people who either can’t manage down or can’t manage up. You give them great people, and the talent just goes there to die.

BC: There’s a lot of talk about autonomy and self-direction, but what do people really want?

SR: Most people say they want autonomy, but what they actually want first is structure. I guarantee when you started at Basic Capital, you wanted to know: “What are my objectives? How do I contribute?”

Once you know your lane, then you want autonomy. Once you’re inside the machine, then you want to be left alone to run. But too often, the managers don’t know what the objective is — and can’t communicate it — because they don’t have clear direction from the top.

BC: So how should smaller or mid-size companies approach all this?

SR: If you're under 500 or 1,000 employees, the key is giving people instant value. And treating every role like a sales job.

BC: What do you mean by that?

SR: Everyone is selling. I’m selling you on my credibility in this conversation. An analyst is selling their insights. A VP is selling their vision. If you’re not communicating your value — inside the company, across teams, up to leadership — then your impact gets lost. That’s true at every level.

BC: So what are you working on selling right now? What should people check out?

SR: Honestly? I’ve got nothing to plug. I wanted to do this because I really believe in what you’re doing. It’s a fascinating idea, and I think it could really help a lot of people.

BC: Appreciate that. But at least tell people where they can find your writing?

SR: Okay, twist my arm. I write a newsletter on LinkedIn where I try to cut through the noise on hiring, retention, benefits, and all the weird, messy parts of building teams. I want to make sense of what I’ve seen work — and what I’ve seen fail, too — inside all kinds of companies.