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HR Insights for Early- to Mid-Stage Founders
Growing a startup comes with challenges that don’t wait until you’re “ready” for them. These posts highlight the turning points and risk areas that can stall growth - and what to watch for - so you can address them before they become costly.
From hiring and retention to compliance and compensation strategy, each insight is written for early- to mid-stage founders and leaders who want to get HR right the first time - and keep it built for scale.
New here? Start with “The Growth Bottleneck” or “Startup Culture Starts at the Top.”
Founder-Focused Insights
Benefits Don’t Close Every Candidate, But They Lose Plenty
Most candidates do not accept a job because of benefits. They accept because of the role, the team, the work, or where the company seems to be heading. Benefits are rarely the deciding factor when someone says yes. But they are often the reason someone hesitates or decides not to move forward. That hesitation does not usually show up clearly. Candidates rarely say that benefits were the issue. More often, the feedback sounds general. The timing is not right. They chose anothe
Steve
Jan 233 min read
Performance Management Is Widely Wanted, and Quietly Avoided
Performance management is widely expected—for growth, alignment, and fair recognition. Yet it often breaks down not because of poor design, but because both employees and managers hesitate around the uncomfortable work it requires.
Steve
Jan 192 min read
When Trust Alone Isn’t Enough to Scale a Startup
Early-stage startups run on trust. Founders know their people. Expectations are mostly implicit. Decisions happen fast. If something’s unclear, it gets handled in a conversation. Context is shared because everyone was there when it was created. At 10 or 15 employees, this works really well. As the company grows, trust stops being sufficient. Nothing suddenly breaks. The same people are still there. The same values apply. But the way the company actually operates starts to cha
Steve
Jan 52 min read
Why Employees Lose Faith - and What Great Founders Do About It
Employees join startups with hope -belief in the team, the mission, and the possibility of something meaningful. But at some point, some lose faith in the promise that brought them in. This post explores why it happens and what great founders do to keep that early hope alive.
Steve
Dec 11, 20252 min read
What Employees Say - But Rarely Openly
Employees share their real experiences privately long before they ever say them out loud. These quiet truths reveal what people feel as companies scale - and what founders often don’t hear until much later.
Steve
Dec 8, 20253 min read
Are Your Portfolio Companies Ready to Scale?
Most startups hit a predictable inflection point between 25–75 employees — too big to wing it, too lean to hire a full-time HR executive. Here’s what investors look for when determining whether a company is truly ready to scale.
Steve
Nov 25, 20254 min read
Startup Stereotypes - How Real They Are, and How Great Founders Lead Through Them
Startups get labeled with the same stereotypes — unstable, overworked, underpaid, unstructured. But most aren’t myths — they’re growing pains. This blog explores how great founders turn those challenges into growth, and how the right HR structure helps them lead through it.
Steve
Oct 22, 20253 min read
The Hidden Co-Employer in Your Company — What Co-Employment Means for Startups and Why Investors Notice
Most founders don’t realize that signing with a Professional Employer Organization (PEO) means sharing legal control of their HR infrastructure. This post explains why that matters - and what investors see when founders give up ownership of their own HR.
Steve
Oct 15, 20253 min read
From Coffee Walks to Identity Shifts: The Startup Growing Pains No One Plans For
Every startup hits an identity shift as it grows - the point where closeness fades and culture starts to drift. This post breaks down why it happens, what it costs, and how to keep your company connected as it scales.
Steve
Oct 6, 20252 min read
Career Velocity - The Startup Advantage Big Companies Can’t Match
Startups enable career velocity big companies can’t match - faster growth, internal leaders, less founder drag. Get the 10-page Career Velocity Guide.
Steve
Sep 12, 20251 min read
Startup Culture Starts at the Top - Early Leaders and Pillars Amplify It.
Culture doesn’t come from a handbook. It starts at the top - with how founders and leaders behave. Early pillars make sure it’s engrained in your company.
Steve
Aug 25, 20251 min read
The Growth Bottleneck: Why Early-Stage Recruiting Makes or Breaks Startup Success
A founder brought me in when their team had exhausted hiring through their network and no longer had the bandwidth to meet their targets. Under 20 employees at the time, we made quick progress on early-stage recruiting — landing key hires and building the foundation to scale.
Steve
Aug 14, 20252 min read
If any of these challenges feel familiar, let’s talk.
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