I’ve Been the First HR Hire at Multiple Startups — Here’s What Founders Need to Know

Most early-stage founders don’t have a People & Talent partner in the room during their first, most important hires. Yet these decisions shape how a company scales from a few employees to 20, 30, or more. I’ve joined startups at various stages — as employee #30, #65, #77, and beyond. In each case, many critical hiring decisions had already been made.

While I can’t personally advise each founder as they go through this, I can share what I’ve learned. My goal is to give you the context and clarity to make early-stage hiring decisions with intention. Here’s what matters most.

Don’t Wait for Talent to Find You

When you’re just starting out, your employer brand equity is low to nonexistent. That means when you post a role, you’re likely to get a wide and unpredictable mix of applicants. Your best bet is to proactively source the talent you want.

Excellence recognizes excellence. Who are the best people you’ve hired or worked with in your career? The people who set the bar high and surround themselves with the best caliber talent? Reach out to these people and find out who they know for the roles you need in your team.

Leverage your investors. Use their networks and existing credibility to amplify your reach. Many VC firms have job boards or dedicated Talent Partners who can help. Don’t be shy about getting support from your investors, they want you to succeed and will help you elevate your team.

Aim high. Focus on who will raise the bar, not just who will say yes. Look for the talent you’d want sitting beside you on the journey. Don’t be afraid of candidate rejection; it’s inevitable. If you think someone would be an amazing fit, reach out. It’s always worth the shot.

Partner with great recruiters. Specialized recruiting firms can accelerate quality hiring without draining your bandwidth. There are so many out there, so it’s important you are selective about where to spend your time and who recommends them. Here are some people and firms I’ve seen tremendous success with that I’d recommend in a heartbeat.

• Product & Engineering (below Director): Kofi Group
• Sales, Marketing, RevOps, Finance, HR: Brit Suits
• Leadership/Executive Search: Parker Remick

Big Tech ≠ Early-Stage Fit

Hiring from big tech can seem like a shortcut to credibility, but it’s not always a fit. Large companies offer structure, resources, and brand recognition that early-stage startups can’t. What works well in one environment often doesn’t transfer.

Early-stage companies need builders: people who thrive in ambiguity, move quickly and embrace the messy middle. Look for those who’ve seen the movie — folks who’ve worked in fast-moving environments and understand what early-stage chaos really looks like.

Hire for Core Attributes First

In my experience, there are three primary core attributes that successful early-stage team members possess:

Intellectual Curiosity

Defined as a deep and genuine desire to learn, explore, and understand beyond what is required. It’s the drive to ask why, how, and what if — seeking new knowledge, questioning assumptions, and pursuing deeper insights.

I realized the importance of intellectual curiosity when I joined Cypress in 2021. I interviewed every employee and asked them the same question: what attributes make someone successful here? Overwhelmingly, people used phrases like “lifelong learners,” “curious,” and “intellectually driven.” At first, I thought it might be a company-specific trait. But as I reflected on other early-stage environments, I noticed this trait showed up again and again. Curious people are learners at heart. They don’t just react; they anticipate, ideate, and iterate. They understand the value of feedback loops and crave knowledge in all forms. And when you’re building, that mindset becomes a superpower.

Self-Awareness

The ability to see yourself from an outsider’s point of view — your behaviors, emotions, impact on others, strengths, development areas, and how the world perceives you.

This is my favorite one because it’s the hardest to interview for and the most critical, in my opinion. At Cypress, our founder and I spent a lot of time identifying the patterns behind our non-regrettable departures. We asked: what did they have in common? The answer: a lack of self-awareness. While having less of it can sometimes reduce self-doubt or hesitation, we found that a high level of self-awareness created the conditions for stronger feedback loops and personal growth. When you’re building something new, you have to iterate quickly. People who are self-aware can take feedback without defensiveness and apply it with intention. That skill alone can drastically improve team cohesion and output.

Impact-Driven

To be impact-driven, you choose outcomes and results over tasks and activities. You focus on the why and the what, knowing that the how will follow.

At DraftKings, I saw this up close during a period of intense growth across our Engineering and Data teams. We hired with incredible precision, and the caliber of talent showed. What stood out most was how impact-oriented these individuals were. They didn’t define success by how many hours they worked or how many tasks they completed. They were relentless about results — questioning, stretching, and refining solutions until they got to the best possible outcome. In early-stage companies where the structure is thin, and priorities shift, people who are anchored in outcomes help you move forward with clarity and velocity.

Attributes Over Skills

Hiring is full of trade-offs. But I’ve rarely seen a skills-first hire (without the right attributes) work out long-term. Skills can be taught. Attributes can’t. I use talent attributes as the first filter and skills as the second. When we do this in the reverse, we likely end up compromising the wrong side of the coin.

If you urgently need a skill set, consider using a contractor or consultant. Flexible, freelance, and fractional talent can join in a pinch to help alleviate productivity strain and enable you to move forward on the priorities you have. Make permanent hires based on who aligns with your company’s values and trajectory.

Every Hire Shapes Culture

Every person you add impacts your culture. One misaligned hire may seem manageable — but small missteps compound. Culture isn’t static; it’s shaped by behavior, consistency, and what you tolerate.

One of the best metaphors I’ve come back to time and again: companies are like ships. As a founder, you’re not just steering — you’re assembling a crew to help you reach your destination faster, navigate smarter routes, and operate as one. But even a few wrong hires can quietly shift your course. A few degrees off may not seem like much at the start, but over time, that slight deviation can take you far from where you intended to go.

Move Fast When It’s Not Working

Fail fast in everything you do but especially in hiring. Cut misaligned hires quickly. Do it with grace, respect, and transparency but don’t let problems linger. Recognize patterns. Adjust the process. Build in feedback loops.

Every stumble is a chance to learn. But only if you’re willing to act.

Final Thought: Hire as If It Matters — Because It Does

Early-stage work is rewarding, hard, and deeply human. Your team is your company. Choose your early crew wisely.

The people you hire now won’t just do the work — they’ll define how the job gets done, how culture evolves, and how resilient your company becomes. With the right crew, you won’t just reach your destination. You’ll discover new ones along the way.