Learn From the Best: Dandy’s Head of Talent on What Makes a Great Recruiter

He took the team from 13 to 650 at lightning speed. Here’s what recruiters and founders can learn from the legend himself.

Learn From the Best: Dandy’s Head of Talent on What Makes a Great RecruiterLearn From the Best: Dandy’s Head of Talent on What Makes a Great Recruiter

When I first met Will Chinburg back in April 2020, my first impression of him was that he was ‘not your average recruiter.’ It felt like Will had built Vettery and Mint House brick by brick (hiring employee after employee) and knew his calling. Will drops into a business when he gets hired, understands the soul, mission, and what needs to get done, then gets to work building best-in-class teams. He is straight to business, no frills, and appreciates that quality in others. He is confident and self aware, moves at a lightning speed, and has one of the sharpest noses for great talent of anyone I’ve ever met. Immediately, I knew exactly who I had to connect him to.

I introduced him to Toni Oloko at Dandy, a business that is modernizing the way dentists practice, when the company was just 12 employees and he was looking for a recruiter to help scale it. Since joining Dandy as the first recruiter and employee #13, Will has scaled the business to over 650 employees. He is my go-to when I want a second opinion, he always has a fresh take on the market, doesn’t compromise for anything below exceptional, and calls it as he sees it.

We invited him to join as the first member of Primary's first Talent Advisor Program, a tight-knit community of elite Talent leaders who advise the portfolio and our team and share candidates that opt-in to be connected to the portfolio. They gain access to the community, our team, and their talent pipelines and discuss best practices, tools, and market observations.

I sat down and asked him some of his secrets of the trade to learn from the best.

How did you first get into recruiting? What drew you in? How did you know you loved it?

I have a lifelong obsession with the idea that work doesn’t have to suck. I was fortunate to grow up in a household in which both my parents loved their jobs, so from a young age, I thought that was the norm for everybody. Then I went out into the real world and discovered that a lot of people really hate their jobs—including some really successful people in traditionally prestigious career tracks. Recruiting gives me the opportunity to bring talented people into organizations that I really believe in. Helping to give someone a meaningful professional existence has always been the biggest perk of the job. I was hooked after the very first hire I made—a marketing coordinator for Vettery in 2016.

What makes you exceptional at your role?

I keep a high talent bar and use a critical eye to evaluate the candidates I bring in. I’ve spent most of my career working directly for founders, who care deeply about who joins their company, especially during the early stages. Working for founders is the best possible way to learn a ruthlessly high talent bar. A lot of recruiters pride themselves on their ability to sell candidates to hiring managers and push them across the finish line, which actually isn’t their job. The job of the recruiter is to produce top-tier candidates, curate a thorough interview process, and advise the team on general best recruiting practice / strategy. Great recruiters never push and only rarely editorialize—if anything, recruiters should talk hiring managers OUT of making offers more than they talk them INTO making offers.

You are a builder, clearly, and have come in as the first recruiter three times and have built out the program from scratch. What advice do you have for others who are building out their talent program from scratch in attracting talent?

  • Source like crazy. If you’re the first recruiter, your company likely has no brand or public image, so organic talent attraction will be low. Create a cold-sourcing engine capable of reaching out to 100 prospects per role per week for your highest priority openings (don’t prioritize more than five roles, or you’ll only make slow, incremental progress on each). Also diversify your sourcing channels using tools like Gem.
  • Screen for intent on your calls and find candidates who believe. In the early stage, you will find plenty of smart, capable, experienced candidates—but the candidates who believe in your business and are willing to take the leap drive the biggest impact.
  • Create shared ownership with your hiring managers, especially the founders. Good founders spend 50% of their time on recruiting. Great founders spend 75% or more—this means taking initial screens, selling and closing candidates, and even sourcing.
  • Aside from the founders, you are the primary spokesperson for the company. Go out of your way to cultivate a best-in-class candidate experience. This closes candidates in the near term and is also an investment in your future talent brand. I lost count of how many candidates weren’t quite ready to join during the super early stage, but came back to us six or nine months later because of their positive experience interviewing the first time around.
  • Don’t over-complicate your tech stack or bring in too many extra tools / agencies / resources. A great first recruiter on the ground should be able to make the first 30+ hires using LinkedIn Recruiter, an ATS, and an email outreach tool (all told, less than $30k in budget). This also forces you to master the environment without relying on anything or anyone else but yourself. It’s a lot like the Sales Exec who comes in and works as an SDR for a week—there is no better way to learn the org and identify areas for improvement.

You’ve scaled out a business from scratch, so you’ve built the culture. How do you assess and build on that culture? What are you looking for in candidates outside of being excellent at their craft?

Strong company culture starts with the fundamentals of your business—are you solving an actual problem? Do you have product market fit? Do your unit economics work? If you’re building a real and sustainable business, anchor your culture to that. If your business doesn’t fundamentally work, building “culture” becomes a superficial exercise in free Friday lunches and dog-friendly office policies.

As a recruiter, my primary contribution to company culture is the people I help bring into the organization. My two biggest indicators for strong culture fit are low ego and professional self-awareness. Low ego candidates are willing to collaborate and work towards the singular goal of getting your company off the ground—whatever it takes. Professionally self-aware candidates know where they are in their career and what experience they need to continue growing. They don’t have overinflated expectations of what scope, title, or compensation they deserve.

What’s been the secret to your success in scaling exceptional teams?

Treat the recruiting process like a science. Above all else, recruiting is a system of inputs and outputs. If you can put high-quality candidates into the top of the funnel, high quality hires inevitably manifest at the bottom. If you source aggressively, screen candidates rigorously, and have a compelling business, you will be successful—plain and simple.

What do you find that candidates in a competitive market care about / ask you about most when they are assessing opportunities?

  • Access to impact and growth: Candidates want to contribute in meaningful ways. They also want to leverage their time at the company to grow and develop their careers.
  • Talent density: Great candidates want to work with great teammates. As a recruiter, show (don’t tell) candidates you have talent density. Include your best teammates in the interview loop as a signal that competitive, experienced operators work at your company.
  • Compensation: 3 or 4 months ago, it was a candidate’s market—fierce competition was driving the cost of talent up 10-20%. Today, with layoffs and uncertainty in private and public markets alike, the balance has shifted back towards the company’s advantage.  But for top flight talent, as in 99th percentile, companies will still need to be aggressive to close the deal. Candidates looking at startups used to expect to take a cash cut in exchange for meaningful work and equity upside. That expectation isn’t really there today; startups need to shell out both cash and equity in equal measure for the very best talent.

What advice do you have for early stage businesses that are looking to compete for top talent? Is it all a numbers game? What can an early stage business do to set themselves apart in this market?

Designate a single-threaded owner of all talent acquisition goals and outcomes. Even if you haven’t brought on your first full-time recruiter, make sure one person has accountability to the rest of the org on hiring (for example your Chief of Staff or first hardcore operator).  This serves as a forcing function that will increase velocity and drive results.

What does a “great recruiting culture” mean to you?

  • Shared ownership of recruiting goals across all stakeholders.
  • Celebrating wins org-wide (I send a team@ announcement for the first 30 or so hires I make at any company).
  • High candidate NPS, especially among candidates who do not get offers.
  • Strong investment in recruiting headcount, resources / tooling, and team-building spend from the leadership team.

Any tricks/tips/advice you can share on how you close a great candidate?

The closing process starts on your very first call. If a typical recruiter screen is 30 minutes, you should be able to identify strong candidates during the first 15 minutes, and start selling on the back half of the call. Find out what matters to them and thread that through the entire interview process. Make sure everyone on the interview loop knows what is important to each candidate.  I always like to ask on that first call: “What are you not getting at your current gig that you want to get elsewhere?”

Recruiters are high in demand. There seems to be a shortage of excellent recruiters, and the market hasn’t seemed to slow down. Do you have any advice for founders/hiring teams looking to hire recruiters specifically? What drew you into Dandy?

  • Look for recruiters who can be both strategic and tactical. Early stage recruiters need to build infrastructure, develop a culture of recruiting, and partner with the business to determine needs and drive growth. But they also need to get their hands really dirty and make hires at the same time. Don’t bring on an overly strategic talent lead who can’t or won’t do the labor required to actually make hires.
  • Place you and your cofounders at the center of the recruiting process. This gives you perspective on the recruiting process, and also sends the signal to prospective recruiter candidates that you are invested in talent acquisition. This was a deciding factor in why I joined Dandy; as soon as my founders raised their Series A, they started looking for a recruiter. Their energy around recruiting was undeniable—it was clear that they saw talent acquisition as essential to the business.

What about for first Heads of Talent? Does your answer change for founders looking for Heads of Talent vs. IC recruiters?

Every recruiter you hire during the early stages should have Head of Talent or some leadership potential. In a high-growth environment, each of your recruiters needs to be autonomous and hard-charging. Also remember that as you grow, your first Head of Talent may have to get layered by someone with more experience building big recruiting systems. A good first Recruiter / Head of Talent might end up hiring their own boss.

Recruiting pulls on a lot of different skill sets—in your opinion what are the most important skills you assess for recruiters?

  • Organization: Can you drive a high volume of recruiting activity without sacrificing work quality or candidate experience? Are you able to leverage tools to automate your work and scale yourself as a recruiter? In a high-growth environment, you must always be able to increase the velocity.
  • Communication: Can you crystalize complex concepts and explain big ideas in simple but effective terms? Do you know when to hold back? Do you ramble or talk too much when you don’t really know what to say? In recruiting, less is more.
  • Data analysis: are you able to advise the team and shape recruiting strategy using data?  If you’re going to push back against hiring managers on process, use hard data instead of anecdotal evidence.  Instead of saying “I feel like we’re not offering competitive compensation for this role,” show your team the last 10 strong candidates you spoke to and what their compensation expectations were.
  • Ambition: Do you have a firm idea of where you want your career to be in the near and long term? Do you want to grow and take on more?  Recruiting is a field where smart hardworking people can go far quickly. I like candidates who recognize this and aspire to keep moving up in their professional trajectory.
  • Sense of humor: early stage recruiting is back-breaking work, and you’re usually getting pulled in 10 different directions at once.  Most successful recruiters I know are able to take a step back and laugh at the situation, at themselves, at anything in order to stay sane